Chiral Luminescence E-Book

• Herausgeber: Wiley-VCH GmbH
• Kategorie: Wissenschaft und neue Technologien
• Sprache: Englisch
• Veröffentlichungsjahr: 2024

Seitenzahl: 1651

Beschreibung

comprehensively illustrate the latest stage and development of Chiral Luminescence in science and technology, from the fundamentals to the applications of emerging circularly polarized luminescence properties and functions.

Leseprobe

Table of Contents

Cover

Table of Contents

Title Page

Copyright

Preface

Acknowledgments

Volume 1

Section I Molecules

1 Synthesis and Properties of Circularly Polarized Luminescence-Active Molecules Based on the Binaphthyl Skeleton

1.1 Introduction

1.2 Synthesis and Properties of Carbon-Chain-Bridged BINOL Derivatives

1.3 Synthesis and Properties of BINOL Derivatives with PA Groups at the 3,3′- to 7,7′-positions of the BINOL Skeleton (3-PA

1

to 7-PA

1

)

1.4 Synthesis and Properties of BINOL Derivatives with Multiple PA Groups

1.5 Conclusions

Acknowledgments

References

2 An Approach for the Qualitative Understanding of Electronic and Magnetic Transition Moments Aiming at the Design of CPL Chromophore Having Enhanced Chiroptical Properties

2.1 Introduction

2.2 What are Electronic and Magnetic Transition Moments,

μ

and

m

?

2.3 Tutorial: Why Previous Researchers Used Carbonyl Compounds as the Model of CPL Chromophore?

2.4 Conclusion

References

3 Optical Resolution and Chiroptical Properties of Partially-Overlapped Carbazolophanes

3.1 Introduction

3.2 Synthesis and Structural Feature of Carbazolophanes

3.3 Optical Resolution of Carbazolophanes

3.4 Photophysical and Chiroptical Properties of Carbazolophanes

3.5 Concluding Remark

References

4 Circularly Polarized Luminescence in Stereogenic π-Conjugated Macrocycles

4.1 Introduction

4.2 Basic Concept of Molecular Design

4.3 Stereogenic Cyclic Oligoarene

4.4 Twisted Cycloparaphenylenes

4.5 Figure-eight System

4.6 Chiral Macrocycles Composed of Acetylene Scaffold

4.7 Summary and Outlook

References

5 Developments in Circularly Polarized Luminescence Research Employing Cyclodextrins

5.1 Introduction

5.2 CPL Induction of Achiral Luminophores in a Cyclodextrin Cavity

5.3 Isolated Cyclodextrin Molecules Exhibiting CPL

5.4 CPL Exhibiting Supramolecular Assembly Consisting of Cyclodextrins

5.5 CPL Derived from Organic Frameworks Consisting of Cyclodextrins

5.6 Conclusion

References

6 Circularly Polarized Luminescence Based on Chiral AIEgens

6.1 Introduction

6.2 Molecular Structures of Chiral AIEgens

6.3 Circularly Polarized Luminescence Based on Chiral AIEgens

6.4 Conclusions

References

7 Planar Chiral [2.2]Paracyclophane: Excellent Circularly Polarized Luminescence Emitters

7.1 Introduction

7.2 Chiral π-Stacked Molecules Based on Planar Chiral [2.2]paracyclophane

7.3 Chiral Cyclic Molecules Based on Planar Chiral [2.2]Paracyclophane

7.4 Control of Axial Chirality, Helicity, and Twisted Chirality by Planar Chirality of [2.2]Paracyclophane

7.5 Conclusion

References

8 Nanometrical Helical Structures as Platform to Induce Chiroptical Properties to Achiral Components

8.1 Introduction

8.2 Molecular and Supramolecular Chirality from Gemini-Tartrate Templates

8.3 Silica Nanohelices as Platforms to Organize Nonchiral Objects

8.4 Conclusion

References

Section II Oligomers and Polymers

9 Synthesis and Chiroptical Properties of Helically Stacked Conjugated Polymers

9.1 Introduction

9.2 CPL of Disubstituted Polyacetylenes with Lyotropic LC Behavior

9.3 Dynamic Switching and Amplification of CPL using Selective Reflection/Transmission of N*-LCs

9.4 Blue CPL of Spherulites with a Higher-Order Helical Structure Consisting of Ionic Conjugated Polymers

9.5 Conclusion

References

10 Synthesis and Chiroptical Properties of Helical, Conjugated Polymers, and Twisted Molecules

10.1 Introduction

10.2 Polyurethane and Cyclic Oligomer

10.3 Polyfluorenes

10.4 Poly(fluorene-2,7-diylethene-1,2-diyl)s [poly(fluorenevinylene)s]

10.5 Poly(benzene-1,4-diyl)s [poly(

p

-phenylene)s]

10.6 Chiral Small Molecules Having Twisted Conformation

References

11 Chiroptical and Magneto-optical Properties of Porphyrin Compounds

11.1 Exciton Chirality of Porphyrin Compounds

11.2 Magnetic Circular Dichroism of Porphyrin Compounds

11.3 Magneto-Chiral Dichroism of Porphyrin Aggregates

11.4 Circular Polarized and Magnetic Circular Luminescence of Porphyrin Aggregates

11.5 Harmonic Light of Chiral Porphyrin Aggregates

References

12 CPL Emission from the Photo-Excited Parallel-Oriented Aryl/Aryl Dimer

12.1 Introduction

12.2 Background of this Chapter

12.3 Examples of Parallelly Oriented Aryl/Aryl Dimer

12.4 Conclusion

References

13 Synthesis, Control of Higher-Order Structures, and Optical Properties of Platinum-Containing Poly(aryleneethynylene)s and Related Compounds

13.1 Introduction

13.2 Synthesis of Pt-containing Poly(aryleneethynylene)s by Sonogashira–Hagihara Coupling Polymerization

13.3 Synthesis of Pt-containing Poly(aryleneethynylene)s by the Dehydrochlorination Coupling Polymerization

13.4 Ligand Exchange Reaction for Controlling the Conformation of Pt-containing Polymers

13.5 Photo-Triggered Chiroptical Switching of Pt Complexes Bearing Azobenzene Moieties

13.6 Aggregation of Pt-containing Conjugated Polymers to Fix Chirality

13.7 Highly Photoluminescent Poly(norbornene)s Carrying Pt–acetylide Complex Moieties

13.8 Summary and Outlook

References

14 Chiroptical Supramolecular Assemblies

14.1 Introduction

14.2 CPL of Organic Luminophores Based on Covalent Bonds

14.3 Helical Supramolecular Assemblies

14.4 CPL Produced by Helical Supramolecular Assemblies

14.5 Stimuli-Responsive CPL Using a Supramolecular Assembly

14.6 Summary

References

15 Circularly Polarized Luminescence (CPL) in Helically Assembled Pyrene π-Stacks on RNA Duplex

15.1 Introduction

15.2 Synthesis of Pyrene-Modified RNA and DNA Oligonucleotide

15.3 Single Pyrene-Modified RNA and DNA: Hybridization, Duplex Conformation, and Fluorescence

15.4 Multiple Pyrene Modification of RNA Double Helix: Helically Assembled Pyrene π-Stacks

15.5 Pyrene Excimer CPL in Helically Assembled Pyrene π-Stacks on RNA Duplex

15.6 Pyrene Excimer CPL in Chiral Organic Molecular System

15.7 Conclusion

References

16 Circularly Polarized Luminescence of Helical Network Polymers Synthesized in Chiral Liquid Crystals

16.1 Introduction

16.2 Liquid Crystals

16.3 Chiral Liquid Crystals

16.4 Polymerization in Liquid Crystals

16.5 Helical Network Polymers Synthesized in Chiral Nematic Liquid Crystals

16.6 HNPs Synthesized in Chiral Smectic Liquid Crystals (S*-LCs)

16.7 Conclusion

References

17 Ultraweak Intermolecular Interactions in Chirogenesis from Noncharged CPL-/CD-Silent Molecules, Oligomers, and Polymers Endowed with Noncharged Chiral Terpenes, Mono-/Polysaccharides, and Helical Polysilanes

17.1 Introduction – The Origins of Homochirality and Recent Progress

17.2 General Concepts, Knowledge, and Understanding of Chirogenesis

17.3 Research Showcase

17.4

E

B

= 5–20 kJ mol

−1

(

E

B

∼ 2–8

kT

)

17.5 Conclusion

17.6 Acknowledgments

References

Section III Coordination Compounds

18 Circularly Polarized Luminescence Induced by an External Magnetic Field: Magnetic Circularly Polarized Luminescence

18.1 Introduction

18.2 Magnetic Circularly Polarized Luminescence from Optically Inactive Organic Luminophores

18.3 Magnetic Circularly Polarized Luminescence from Organic–Inorganic Luminescent Materials

18.4 Magnetic Circularly Polarized Luminescence from Inorganic Luminescent Materials

18.5 Conclusion

References

19 Phosphorescent Organometallic Complexes Aimed at Fabrication of Electroluminescent Devices

19.1 Introduction

19.2 Device Structures and Device Fabrication of OLED

19.3 Phosphorescent materials in OLED

19.4 Phosphorescent Iridium(III) Complexes for OLED Application

19.5 Phosphorescent Platinum(II) Complexes for OLED Application

19.6 External Magnetic Field-Driven CPL From Phosphorescent Organometallic Emitters

19.7 Concluding Remarks

References

Volume 2

20 Enhancement of Circularly Polarized Luminescence in the Condensed Molecules and Coordination Complexes

20.1 Introduction

20.2 Challenges of CPL Measurements in the Solid State

20.3 Excitonic Coupling Effect and Excimers

20.4 Aggregation-induced CPL Enhancement

20.5 AIEgens

20.6 Chiral Dopants

20.7 Achiral Dopants

20.8 Other Studies in Organic Systems

20.9 Challenges for Eye-detectable CPL with Multinuclear Eu(III) Systems

References

21 Control of the Emission and Chiroptical Properties of Helicene Derivatives

21.1 Introduction

21.2 Control of the Emission Properties of [5]Helicene Derivatives

21.3 Control of the Emission Properties of [7]Helicene Derivatives

21.4 Control of the Emission Properties of Figure-Eight-Shaped [5]Helicene Dimer with

D

2

Symmetry

21.5 Conclusions

Acknowledgments

References

22 Recent Advances on CP-OLEDs and CPL-Active Materials of Chiral Metal-Containing Complexes

22.1 Introduction

22.2 CP-OLEDs Based on Versatile EML of Chiral Dyes

22.3 CPL Materials Based on Metal-Containing Coordination Compounds

22.4 Summary and Perspectives

References

23 Evolving Fluorophores into Circularly Polarized Luminophores with Chiral Naphthalene Dimers and Tetramers

23.1 Introduction

23.2 Fluorophore-Tethered Naphthalene Dimers and Tetramers

23.3 Binaphthyl–Pyrene Sandwich Dyes and Binaphthyl-Bridged Pyrenophane

23.4 Binaphthyl–Bipyridyl Cyclic Dyads and the Bipyridyl–Ruthenium Complexes

23.5 Binaphthyls with Trialkylsiloxy Groups

23.6 Conclusion

References

24 Polarized Luminescence of Lanthanide Coordination Compounds

24.1 Scope of this Chapter

24.2 Publication Trend on CPL of Lanthanide Complexes

24.3 Luminescence Properties of Ln Complexes and Photo-Antenna Effect for Sensitization of ff-Emissions

24.4 Molecular Design of Lanthanide Complexes for CPL

24.5 Molecular Film Formation and Polarized Luminescence of Lanthanide Complexes

24.6 Summary and Perspective

References

25 CPL in Chiral Metal Nanoclusters

25.1 Introduction

25.2 Intrinsic Chirality in NCs

25.3 CPL in Metal Nanoclusters

25.4 CPL in Aggregates or Self-assemblies of Metal NCs

25.5 Chirality Control in Metal NCs

25.6 Summary

References

26 Circularly Polarized Luminescence Chromophores Based on Metal Complexes

26.1 Introduction

26.2 Ligation Manner Induces CPL

26.3 Helical Chirality of Metal Complexes and Their CPL

26.4 Porphyrin-Based CPL

26.5 Conclusion

References

Section IV Theory and Spectroscopy

27 Recent Advancement of Circularly Polarized Luminescence of Helicenes

27.1 Introduction

27.2 [4]Helicene

27.3 [5]Helicene

27.4 [6]Helicene

27.5 [7]Helicene

27.6 [8]- and [9]Helicenes

27.7 Helicene-embedded Nanographene

27.8 Application of Helicenes in Optoelectronic Devices

27.9 Concluding Remarks

References

28 Systematic Investigation on CPL Properties of Various Chiral Motifs Through Theoretical Calculation

28.1 Introduction

28.2 Prediction of CPL Properties by TDDFT Method

28.3 Examples of the Prediction of CPL Properties

28.4 Conclusion

Appendix

References

29 Principles of CPL Measurement Systems and Advances in Measurement Methods

29.1 Introduction

29.2 Principles of CPL Measurement Systems

29.3 Advanced CPL Measurement Methods

29.4 Summary

Acknowledgments

References

30 Using Chiroptical Spectroscopy to Gain Unique Information about the Solid-State

30.1 Introduction

30.2 Instrumentation

30.3 Applications

30.4 Conclusion

References

31 Circularly Polarized Luminescence for Molecular Systems of Increasing Complexity

31.1 Introduction

31.2 Discussion

31.3 Conclusions

References

32 Luminescence and CPL Spectra of d

10

Metal Complexes

32.1 Introduction

32.2 CPL of Copper(I) Complexes

32.3 CPL of Silver(I) and Gold(I) Complexes

32.4 Palladium(0) Complexes

32.5 Concluding Remarks

References

Section V Devices for Application

33 Development of Organic Light-Emitting Diodes using Aggregation-Induced Enhanced Circularly Polarized Luminescent Perylene Diimides

33.1 Introduction

33.2 Circularly Polarized Light-Emitting Devices

33.3 Supramolecular Assembly of Chiral Perylene Diimide Derivatives

33.4 Solid-state Photophysical Properties of Chiral PDI Derivatives

33.5 Chiroptical Properties of Thin Film of Chiral BPP and Their CP-OLED Devices

33.6 Conclusions

References

34 Chiroptical Properties Enhancement of Chiral Eu(III) Complex in Association with Ionic Materials such as DNA Toward Device Application

34.1 Introduction

34.2 Chiroptical Enhancement of Chiral Eu(III) Complex by Alkyl Ammonium Salts

34.3 Chiroptical Enhancement of Chiral Eu(III) Complex in Association with DNA

34.4 Electrochemiluminescence Devices Using Lanthanide Materials

34.5 Conclusion and Future Scopes

Acknowledgments

References

35 Circularly Polarized Luminescence Materials and Their Organic Light-emitting Device Performances

35.1 Introduction

35.2 Chiral Emitter for CP-OLED

35.3 Conclusions and Outlook

References

36 Intense and Sign-Invertible Circularly Polarized Luminescence

36.1 Introduction to Chiral Luminescence

36.2 Sign Inversion of CPL via Coordination Changes

36.3 Sign Inversion of CPL by Photo-triggered Processes

36.4 Sign Inversion of CPL via Excimer Formation

36.5 Sign Inversion of CPL via Structural Modifications

36.6 Sign Inversion of CPL via Physical Methods

36.7 Conclusions and Outlook

References

37 Direct Emission of Circularly Polarized Light from Twisted Structure of Mesogenic Luminophores and Improvement of OLEDs

37.1 Introduction

37.2 OLED and Direct Emission of Polarized Light

37.3 Twisted Structure by Doping Chiral Molecules

37.4 Numerical Analysis of CP Light in Twisted Structure

37.5 Twisted Structures without Chirality

37.6 Twisted Structure via Vacuum Evaporation

37.7 Concluding Remarks

References

38 Binding Constants as Fundamental Physical Properties for Quantitative Treatments of Sensing Processes in Supramolecular Systems

38.1 Introduction

38.2 Fundamental Binding Processes and a Practical Course for Determination of Binding Constant

38.3 Determination of Stoichiometry

38.4 Evaluation of Complex Concentration

38.5 Precautions to be Taken when Setting Up Concentration Conditions of the Titration Experiment

38.6 Data Treatment

38.7 Application Guide for Luminescence Methods

38.8 Application Guide for CD and CPL Methods

38.9 Conclusion

Appendix

Appendix

References

Index

End User License Agreement

List of Tables

Chapter 1

Table 1.1 Optical properties of 6-PA

n

and 7-PA

n

.

Table 1.2 Electronic transition characteristics obtained by RI-CC2/def2-TZV...

Table 1.3 Optical properties of 3-PA

1

to 7-PA

1

.

Table 1.4 Optical properties of the tetra- and hexa-PA

1

compounds.

Chapter 3

Table 3.1 Cyclization conditions and yields of CZPs prepared from 3

n

and am...

Table 3.2

1

H NMR chemical shifts (ppm) of aromatic protons of 1

3

Me and CZPs...

Table 3.3 Optimized separation conditions of racemic CZPs.

Table 3.4 |

g

lum

| values of CZPs.

Table 3.5 Dihedral angles between two Cz least squares planes, the distance...

Chapter 5

Table 5.1 Sizes and physical properties of CyDs.

Table 5.2 Photophysical and chiroptical properties of PCDs.

Chapter 9

Table 9.1

g

abs

of the disubstituted LCPAs in CHCl

3

solution, cast film, and...

Table 9.2 Emission dissymmetry factors (

g

em

) of the disubstituted LCPAs in ...

Table 9.3 Emission dissymmetry factors (

g

em

), wavelengths, and handedness o...

Chapter 16

Table 16.1 Mixing ratios of host N-LCs, chiral dopants, and monomer mixture...

Table 16.2 Spectroscopic data for absorption (

λ

max

), fluorescence (

E

ma

...

Table 16.3 Mixing ratios of the host S

C

-LC, the chiral dopant, and the mono...

Table 16.4 Spectroscopic data for dissymmetry factors of absorption (

g

abs

) ...

Chapter 19

Table 19.1 Device performance of Device-M1 and -M2.

a

Table 19.2 MCPL profiles of Ir(piq)

3

, Ir(ppy)

3

, FIrpic, and Ir(BT)

2

(acac) i...

Chapter 21

Table 21.1 Emission properties of the [5]helicene derivatives.

Table 21.2 Electronic transition properties of 8, 9, and 10.a)

Table 21.3 Emission properties of the [7]helicene derivatives.a)

Table 21.4 Dissymmetry factors of the [7]helicene derivatives.a)

Table 21.5 Electronic transition properties of figure-eight-shaped molecule...

Table 21.6 Absorption and fluorescence properties of 16 and 1.

Chapter 25

Table 25.1 Ligand structure, sample state, and |

g

PL

| of chiral metal NCs

Chapter 27

Table 27.1 Emission properties of recent [4]helicenes.

Table 27.2 Emission properties of recent [5]helicenes.

Table 27.3 Emission properties of recent [6]helicenes.

Table 27.4 Emission properties of recent [7] helicenes.

Table 27.5 Emission properties of recent [8]- and [9]helicenes.

Table 27.6 Emission properties of helicene-embedded nanographenes.

Chapter 28

Table 28.1 Experimental and calculated (CAM-B3LYP/aug-cc-pVDZ) spectroscopi...

Table 28.2 Observed and calculated chiroptical properties of 18–20.

Table 28.3 Observed and calculated chiroptical properties of 21–23.

Table 28.4 Observed and calculated

g

lum

values of 30–33.

Table 28.5 Observed and calculated

g

lum

values of 34–38.

Table 28.6 Observed and calculated

g

lum

values of 39–42.

Table 28.7 Observed and calculated

g

lum

values of (

S

p

)-47, (

S

p

)-48, and (

S

p

Table 28.8 Observed and calculated

g

lum

values of 50–54.

Chapter 30

Table 30.1 Secondary structure of Aβ (1–40) and (1–42) in the aqueous solut...

Chapter 31

Table 31.1 Characteristics of the first electronic transition in the ground...

Chapter 33

Table 33.1 Fluorescence decay times

τ

(ns) and relative amplitude

a

(%...

Chapter 34

Table 34.1 Luminescence lifetimes (

τ

), total quantum yields (

Φ

tot

Chapter 37

Table 37.1 Intensities with a circular polarizer for various samples.

List of Illustrations

Chapter 1

Figure 1.1 Relationship between the number of carbon atoms in the crosslink ...

Figure 1.2 Molecular structures of 6-PA

n

and 7-PA

n

.

Figure 1.3 Synthetic route for 6-PA

1

.

Figure 1.4 (a, b) UV-vis, (c, d) CD, (e, f) FL, and (g, h) CPL spectra of 6-...

Figure 1.5 HOMOs and LUMOs of (a) 6-PA

1

and (b) 7-PA

1

in the gro...

Figure 1.6 HOMOs and LUMOs of (a) 6-PA

1

and (b) 7-PA

1

in the exc...

Figure 1.7 Conformations of (a) 6-PA

1

and (b) 7-PA

1

in the excit...

Figure 1.8 (a) HOMO and LUMO and (b) conformation of 6-PA

Me

in the exc...

Figure 1.9 Halogenation of BINOL derivatives by conventional methods.

Figure 1.10 Synthesis of 4-PA

1

.

Figure 1.11 Synthesis of 5-PA

1

.

Figure 1.12 (a) UV-vis, (b) FL, (c) CD, and (d) CPL spectra of 3-PA

1

t...

Figure 1.13 Synthesis of 3,6-PA

1

.

Figure 1.14 Synthesis of 5,6-PA

1

.

Figure 1.15 Synthesis of 6,7-PA

1

.

Figure 1.16 Synthesis of 3,4,6-PA

1

.

Figure 1.17 (a) UV-vis, (b) FL, (c) CD, and (d) CPL spectra of 3,6-PA

1

Figure 1.18 HOMOs and LUMOs of the tetra- and hexa-PA

1

compounds.

Chapter 2

Figure 2.1 Treatment of position operator...

Figure 2.2 Operation of

x

, ...

Figure 2.3 Operation of

z

on the HOMO (11) of naphthalene 10 generating wav...

Figure 2.4 Polar coordinate system defined on the unit sphere

r

and two angl...

Figure 2.5

z

operations on 1s, 2p

x

, 2p

y

, 2p

z

orbitals.

Figure 2.6 ...

Figure 2.7

z

operations on 3d

z

orbital.

Figure 2.8 (a) Schematic drawing of the 1s orbital wavefunction at

r

=

r

0

an...

Figure 2.9 The

z

operation on the wavefunction of 2p

z

orbital (12). Stepwis...

Figure 2.10 The

z

operation on the wavefunction of 2p

x

orbital (16). Stepwi...

Figure 2.11 The

z

operation on the wavefunction of 2p

x

orbital (20). Stepwi...

Figure 2.12 (a) Partial differentiation on the wavefunction of 2p

y

orbital w...

Figure 2.13 The

z

operation on the wavefunction of orbital (23). Stepwise...

Figure 2.14 (a) Energy diagram of molecular orbital of water 26. (b) Shapes ...

Figure 2.15 Molecular structures of some chiral ketones 35, 35, and 37 studi...

Figure 2.16 (a) Energy diagram of molecular orbital of formaldehyde 38. (b) ...

Chapter 3

Figure 3.1 Chemical structure of Cz and PVCz.

Figure 3.2 Chemical structure of PCDTBT1 and Spiro-OMeTAD.

Figure 3.3 Chemical structure of CBP.

Figure 3.4 The molecular structure of Cz-dicyanobenzene derivatives.

Figure 3.5 Partially-overlapped (PO) and fully-overlapped (FO) carbazolophan...

Figure 3.6 The proposed structure of two types of excimer in Cz chromophore....

Scheme 3.1 Synthetic route of Carbazolophanes.

Figure 3.7

1

H NMR spectra of (a) PO-CZP 4a

3

and (b) FO-CZP 5a

3

(CDCl

3

, 400 M...

Figure 3.8 Chemical structure of CZpPhTrz.

Figure 3.9 Chiral HPLC traces for 4c

n

. (a) 4c

2

with DCM as eluent (left) and...

Figure 3.10 Chemical structures of chiral amines.

Scheme 3.2 Cyclization reaction between chiral amine 8d and 3

3

.

Figure 3.11 X-ray analysis of the compound with

R

f

= 0.35.

Figure 3.12

1

H NMR spectra of a mixture of diastereomers, (

S

p

R

)-9PO, and (

R

p

Figure 3.13 The molecular structure of planar chiral tetrasubstituted [2.2]p...

Figure 3.14 (a) Electronic absorption spectra of 1

3

(red), (

S

p

,

R

)-9PO (green...

Figure 3.15 Alignments of transition dipole moments in PO- and FO-CZPs. The ...

Figure 3.16 Exciton band diagram for a molecular dimer with (a) parallel and...

Figure 3.17 Fluorescence spectra of 1

3

(red), (

S

p

,

R

)-9PO (green), (

R

p

,

R

)-9PO

Figure 3.18 Electronic absorption spectra (A) and fluorescence spectra (F) o...

Figure 3.19 Molecular structures of 4a

3

(left) and 4a

4

(right).

Figure 3.20 ORTEP drawings (50% probability ellipsoids) for crystals of the ...

Figure 3.21 (a) CD spectra of 4b

3

in THF at 25 °C. Blue and red lines corres...

Figure 3.22 CD spectra of 4a

3

in THF at 25 °C. Blue (F1) and red (F2) lines ...

Figure 3.23 Theoretical (solid) and experimental (dashed) CD spectra of (

R

p

)...

Figure 3.24 CD spectra of 4c

2

(left) and 4c

4

(right) in benzene. Red (F1) an...

Figure 3.25 Chemical structures of optically pure CZPs.

Figure 3.26 The

g

lum

charts of cyanamide-bridged PO-CZPs, 4a

n

. (a) 4a

2

, (b)...

Figure 3.27 The

g

lum

charts of

tert-

butylamine-bridged 4c

n

. (a) 4c

2

, (...

Figure 3.28 The

g

lum

charts spectra of (a) 4a

2

and (b) 4c

3

, dispersed in KBr...

Figure 3.29 CD spectra (left) of phenetylamine-bridged (

S

p

,

R

)-9PO (green) an...

Figure 3.30 CPL spectrum (top) and

g

lum

chart (bottom) of (

R

)-9FO in benzen...

Figure 3.31 Molecular structure of cyanamide-bridged 4a

3

(CCDC 151873) and d...

Chapter 4

Figure 4.1 (a)

D

4

symmetric alleno-acetylenic macrocycle 1 (b) Side view of ...

Figure 4.2 Molecular structures of highly symmetrical CPL-emitter.

Figure 4.3 Schematic of two types of macrocycle synthesis by Ni(cod)

2

. Chira...

Figure 4.4 Cylinder-shaped molecules of (

P

)-(12,8)-5a...

Figure 4.5 (a) Macrocyclization of pyrene by Ni(cod)

2

. (b) Woven-pattern mol...

Figure 4.6 (a) Relationship between the dihedral angle

θ

A

and helicity....

Figure 4.7 Molecular structures of 11 and 12.

Figure 4.8 Molecular structure of [8]CPP and schematic illustration of calcu...

Figure 4.9 Molecular structures of 14 and 15.

Figure 4.10 (a) Molecular structure of (

S

)-16. (b) CPL spectra of (

S

)-16 in ...

Figure 4.11 Molecular structures of 17, 18, 19, and 20.

Figure 4.12 (a) Rh-catalyzed [2+2+2] cycloaddition and molecular structure o...

Figure 4.13 Molecular structures of 23 and 24.

Figure 4.14 (a) Synthesis of 28 (b) Molecular structure of 29.

Figure 4.15 (a) Molecular structures of 30a–c and related compounds (b...

Figure 4.16 Figure-eight BODIPY dimer 32.

Figure 4.17 Molecular structures of (a) (

R

...

Figure 4.18 Molecular structures of 35-[

n

] (

n

= 2–4).

Figure 4.19 Molecular structures of parallel-#-36 and weave-#-37.

Figure 4.20 Molecular structure of (a) (

M

)-38 and (

M

)-39 (b) (

P

)-(

E

,

E

)-40 an...

Figure 4.21 Molecular structures of 41 and 42.

Chapter 5

Figure 5.1 (a) Chemical structures of CyDs, and (b) schematic representation...

Figure 5.2 (a) Chemical structure of fluorescein. (b) Total luminescence (TL...

Figure 5.3 (a) Chemical structures of pyrene, P(3)P, and M-γ-CyD. (b) Fluore...

Figure 5.4 (a) Schematic representation of pyrene-[4]rotaxane and perylene-[...

Figure 5.5 (a) Chemical structures of PCDs. (b) Calculated PCD-C0 stru...

Figure 5.6 Photophysical and chiroptical properties of PCDs. (a) UV–vis and ...

Figure 5.7 (a) Schematic representation of supramolecular assemblies of PGAc

Figure 5.8 (a) Schematic representation of CPL emission form supramolecular ...

Figure 5.9 (a) Chemical structures of AC-P4 and AD-P4, and the q...

Figure 5.10 (a) Chemical structures of ThT and SDS. (b) Schematic representa...

Figure 5.11 Schematic representations of thermoresponse of supramolecular as...

Figure 5.12 (a) Chemical structures of CG and the supramolecular complex for...

Figure 5.13 (a) (i) Two typical examples of CPL materials based on CyDs and ...

Figure 5.14 (a) Synthesis process for two-dimensional chiral polyrotaxane (2...

Chapter 6

Figure 6.1 Photos of perylene (a) and hexaphenylsilole (HPS) (b) taken under...

Figure 6.2 Molecular structures of silole-based chiral AIEgens.

Figure 6.3 Molecular structures of cyanostilbene-based chiral AIEgens.

Figure 6.4 Molecular structures of TPE-based chiral AIEgens.

Figure 6.5 Molecular structures of TPE-BINOL-based chiral AIEgens.

Figure 6.6 Molecular structures of chiral TPE-based polymers.

Figure 6.7 Molecular structures of other chiral AIEgens.

Figure 6.8 Molecular structures of prochiral AIEgens.

Figure 6.9 Molecular structures of chiral induction through supramolecular A...

Figure 6.10 (a) PL spectra of 1 in a mixed solvent of dichloromethane and he...

Figure 6.11 (a) Chemical structure of 20. (b) SEM image of xerogel made from...

Figure 6.12 (a) UV absorption and (b) CD spectra of 5 in 1,2-dichloroethane ...

Figure 6.13 (a) CD spectra of (

R

)-/(

S

)-48 in THF and (b) in THF/H

2

O 5 : 95. ...

Figure 6.14 (a) Molecular structure of 93 and its crystal structures. (b) PL...

Figure 6.15 (a) Molecular structure 109 and different AIEgens. A schematic d...

Figure 6.16 (a) Device structure of a top-emission CP-OLED built by a typica...

Chapter 7

Figure 7.1 Structure of [2.2]paracyclophane, its planar chirality, and subst...

Figure 7.2 Structures and CPL profiles of (

R

p

)-V(60)-1, (

S

p

)-V(120)-2, (

R

p

)-...

Figure 7.3 Molecular orbitals and simulated transition dipole moments (μ...

Figure 7.4 Structures of X-shaped molecules and the dendrimer.

Figure 7.5 Vessel-shaped microcrystals of (

S

p

)-X-8 and the use of the microc...

Figure 7.6 Structures of V- and X-shaped molecules with the extended π-elect...

Figure 7.7 CPL change of the solution and the thin films of X-shaped molecul...

Figure 7.8 V-Shaped molecules consisting of

p

-arylenes.

Figure 7.9 Structures of coumarin-stacked [2.2]paracyclophane and PRODAN-bas...

Figure 7.10 Structures of CP-TADF emitters.

Figure 7.11 Synthesis of [2.2]paracyclophane-based cyclic trimer and polymer...

Figure 7.12 Plausible zig-zag and folded helical structures of the linear tr...

Figure 7.13 Structures of thiophene- and selenophene-containing molecules.

Figure 7.14 Structures of cyclic dimer and trimer consisting of

para

-quaterp...

Figure 7.15 Structures of cyclic dimer, trimer, and tetramer based on

para

-a...

Figure 7.16 Structures of cyclic trimer to hexamer by the oxidative coupling...

Figure 7.17 #-Shaped cyclic tetramers based on

para

-arylene-ethynylene.

Figure 7.18 Structure of a one-handed double helical molecule.

Figure 7.19 Structures of propeller-shaped cyclic molecules.

Figure 7.20 Structures of an X-shaped molecule based on

para

-arylene.

Figure 7.21 VT-CPL spectra of the X-shaped molecule in methylcyclohexane (1....

Figure 7.22 Plausible CPL-emission mechanism of the X-shaped molecule.

Figure 7.23 Cyclic molecule consisting of folded

o

-arylene-ethynylene.

Figure 7.24 Cyclic molecules consisting of pseudo-

meta

-diethynyl[2.2]paracyc...

Figure 7.25 Helicene-stacked molecules: control of helicity by planar chiral...

Figure 7.26 Structure of anthracene-containing cyclic molecule: control of t...

Chapter 8

Figure 8.1 Chemical structure of 16-2-16

L

-tartrate. Transmission electron m...

Figure 8.2 (a) Schematic illustrations of cross-sectional surfaces of nanori...

Figure 8.3 (a) Schematic illustration of the preparation procedure of lantha...

Figure 8.4 (a) Process for the preparation of silica helices covalently graf...

Figure 8.5 Silica nanohelices synthesized from sol–gel condensation of TEOS ...

Figure 8.6 (a) TEM image of nanohelices@PNCs and the cross-sections obtained...

Figure 8.7 (top) Schematic representation of silica-coated organic nanohelic...

Figure 8.8 Molecular structures of achiral inorganic or polyaromatic anions....

Figure 8.9 CD (top) and UV-vis absorption (bottom) spectra of RH- (red lines...

Figure 8.10 CPL and fluorescence spectra of (a) PSA (ex 340 nm), (b) PTCTK (...

Figure 8.11 Multistep transmission of chirality information from tartrate an...

Chapter 9

Figure 9.1 Structures of the disubstituted LCPA derivatives and chiral dopan...

Figure 9.2 (a) POM image of the N*-LC phase of (

S

)-PA2 in a 10 wt% lyotropic...

Figure 9.3 Schematic model of the chiral induction in (

rac

)-PA2 to form an N...

Figure 9.4 UV-vis (upper) and CD spectra (lower) in CHCl

3

solution (

c

 = 1.2 ...

Figure 9.5 UV-vis (upper) and CD spectra (lower) of (a) (

R

)-/(

S

)-PA1 cast fi...

Figure 9.6 PL (upper), CPL (middle), and

g

em

(lower) spectra of (a) (

R

)-/(

S

)...

Figure 9.7 Structures of the N-LC hosts PCH302 and PCH304, chiral dopants (

R

Figure 9.8 PL emission (black) of the (

R

)-PA2 film upon excitation at 367 nm...

Figure 9.9 (a) Schematic representation of the (

R

)-PA2/(

S

)-N*-LC CPL-switcha...

Figure 9.10 Poly(

para

-phenylene) derivative (PPP) and binaphthyl derivatives...

Figure 9.11 (a) UV-vis absorption, CD, and

g

abs

spectra and (b) PL, CPL, and...

Figure 9.12 SEM images of the polymer assemblies (PPP-BNP) (1.0 : 2.0 mol mo...

Figure 9.13 (a) Plausible model of assembly of polymers with the helically π...

Chapter 10

Chart 10.1 Polymers having helical conformation for CPL applications....

Scheme 10.1 Synthesis of helical poly(BINOL-

alt

-27DIF) and BINOL-

alt

-...

Figure 10.1 CD-UV spectra of poly((

R

)-BINOL-

alt

-27DIF)s of

M

n

’s 4100 (a) and...

Figure 10.2 Crystal structure of cyclic dimer of (

S

)-BINOL and 27DIF (A) and...

Figure 10.3 CPL spectra (a), total emission (PL) spectra (b), and

g

lum

spect...

Figure 10.4 CD/UV spectra of poly(DOF) (

M

n

76,700) films prepared by irradia...

Scheme 10.2 Stepwise chirality switching on racemic poly(DOF) (

s

G

 = 0...

Figure 10.5 ECD spectra calculated at the ZINDO level for the negative (−) a...

Scheme 10.3 CPL-driven chirality induction mechanism of poly(DOF)....

Scheme 10.4 Enantiomer-selective

twisted-coplanar transition

(

T

...

Scheme 10.5 Photo-induced racemization of poly(2,7-bis(4-

t

-butylpheny...

Figure 10.6 Circularly polarized luminescence (a), total luminescence (b), a...

Scheme 10.6 Synthesis of chiral poly(fluorene-2,7-diylethene-1,2-diyl...

Figure 10.7 CD-UV spectra of poly(fluorene-2,7-diylethene-1,2-diyl)s (a) at ...

Figure 10.8 Representation of ten chains of 55-mer models of poly(NMPF-E...

Figure 10.9 Experimental CPL spectra (A-a), total emission (PL) spectra (A-b...

Scheme 10.7 Structures of chiral poly(benzene-1,4-diyl)s.

Figure 10.10 CPL emission spectra (a), total emission (PL) spectra (b), and

Figure 10.11 CPL emission spectra (a), total emission (PL) spectra (b), and

Scheme 10.8 Star-shaped molecules, S1, S2, and S3, emitting blue ligh...

Figure 10.12 Experimental CD spectra induced upon L-CPL irradiation (a) and ...

Figure 10.13 Circularly polarized luminescence (top), DC (middle), and

g

lum

...

Chapter 11

Figure 11.1 Electronic absorption spectra of ZnOEP (solid line) and ZntBPc (...

Figure 11.2 Four frontier π molecular orbital energies of Zn porphyrin and Z...

Figure 11.3 Explanation of exciton chirality using a porphyrin dimer. (a) Mo...

Figure 11.4 (a) Preparation methods for chiral aggregates of phthalocyanines...

Figure 11.5 Representative explanation for intensifying MCD by the orbital a...

Figure 11.6 (a) Molecular structures of low-symmetry H

2

TAP derivatives, 1H

2

,...

Figure 11.7 Molecular structure of PtOEP and electronic absorption (upper, s...

Figure 11.8 Molecular structures of (a) H

4

TPPS

4

and (b) J-aggregates of H

4

TP...

Figure 11.9 (a) Molecular structure of ZnChl and (b) schematic image of the ...

Figure 11.10 Laser wavelength dependence of the THS (a, b) and SHS and (c, d...

Chapter 12

Figure 12.1 CPL from chiral pyrene excimer encapsulated in

γ

-cyclodextr...

Figure 12.2 Three types of parallelly oriented aryl/aryl dimer using naphtha...

Figure 12.3 Uv-vis, fluorescence, and CPL spectra of D2 (left), n3 (center),...

Scheme 12.1 Synthesis of NDI dimers.

Figure 12.4 Transition density matrix (TDM) mapping for D2 in AO basis. TDM ...

Figure 12.5 Transition density matrix (TDM) mapping for n3 in AO ...

Figure 12.6 Transition density matrix (TDM) mapping for n5 in AO basis. TDM ...

Figure 12.7 Transition electric density matrix (TEDM) and transition magneti...

Scheme 12.2 Synthesis of 1,4(2,6)-dinaphthalenacyclohexaphane.

Figure 12.8 Uv–vis, fluorescence, and CPL spectra of 1,4(2,6)-dinaphthalenac...

Figure 12.9 Transition density matrix (TDM) mapping for 1,4(2,6)-dinaphthale...

Figure 12.10 Transition electric density matrix (TEDM) and transition magnet...

Chapter 13

Scheme 13.1 Synthesis of poly(aryleneethynylene)s bearing Pt in the m...

Figure 13.1 Pt-containing optically active poly(phenyleneethynylene)s with v...

Scheme 13.2 Synthesis of poly(aryleneethynylene)s bearing Pt in the m...

Scheme 13.3 Ligand exchange reaction of a Pt(PPh

3

)

2

-containing polyme...

Figure 13.2 Possible structures of Pt[Ph

2

P(CH

2

)

m

PPh

2

]-containing polymers (

m

Figure 13.3 Top and tilt views of a 12-mer model for a Pt[Ph

2

P(CH

2

)

3

PPh

2

]-co...

Scheme 13.4 Ligand exchange reaction of a Pt(PPh

3

)

2

-containing polyme...

Scheme 13.5 Ligand exchange reaction of a Pt(PPh

3

)

2

-containing polyme...

Scheme 13.6 Photoisomerization of azobenzene moieties of a Pt complex...

Scheme 13.7 Synthesis of Pt-containing polymers bearing amino-acid-fu...

Scheme 13.8 Synthesis of Pt(bipyridine)-containing polymers bearing a...

Scheme 13.9 Synthesis of a polynorbornene bearing Pt moieties at the ...

Scheme 13.10 Synthesis of polynorbornenes end-functionalized with Pt–...

Chapter 14

Figure 14.1 CPL-active supramolecular assembly.

Figure 14.2 CPL-active PBI attached to binaphthyl unit.

Figure 14.3 CPL-active chiral cyclophanes.

Figure 14.4 (a) One-dimensional hydrogen bond network of amide units. (b) He...

Figure 14.5 Induction of helicity in helical supramolecular assembly.

Figure 14.6 CPL-active supramolecular assembly of PBI derivatives 6.

Figure 14.7 CPL-active helical assembly of pyrene derivatives 7.

Figure 14.8 CPL-active helical assembly of PBI derivatives possessing tris(p...

Figure 14.9 CPL-active helical assembly of a Pt(II)phenylbipyridine complex ...

Figure 14.10 CPL-active helical assembly of organic luminophores possessing ...

Figure 14.11 CPL-active helical assemblies of organic luminophores.

Figure 14.12 Fmoc-protected tripeptides for constructing helical HHAs.

Figure 14.13 CPL-induction through encapsulation by coordination capsule 14....

Figure 14.14 Photoresponsive CPL-active polymers.

Figure 14.15 CPL-active helical assembly of a photoresponsive oligo-

p-

Figure 14.16 Gelation-induced CPL of 19, a Pt(II)phenylbipyridine complex po...

Figure 14.17 Anion-responsive CPL of pyrrole-based anion-receptors.

Figure 14.18 Solvent polarity responsive CPL of tetraphenylethylene derivati...

Chapter 15

Figure 15.1 Sequences and structures of single pyrene-modified DNA and RNA o...

Figure 15.2 (Panel a) shows UV-melting curves for the pyrene-modified RNA ol...

Figure 15.3 (a) CD spectra for the pyrene-modified RNA duplex, I/VIII (bold ...

Figure 15.4 Fluorescence spectra for the single-strand pyrene-modified RNA (...

Figure 15.5 Pyrene is located outside the pyrene-modified RNA duplex, as sho...

Figure 15.6 Sequences and structures of multiple pyrene-modified RNAs.

T

m

va...

Figure 15.7 CD (a) and fluorescence (b) spectra for the pyrene-modified dupl...

Figure 15.8 Sequences of pyrene-modified RNAs, duplex melting temperatures, ...

Figure 15.9 (Panel a): Schematic representation of duplex formation of multi...

Figure 15.10 Fluorescence (a) and CD (b) spectra for pyrene-modified RNA dup...

Figure 15.11 Sequences of multiple pyrene-modified RNAs used for CPL measure...

Figure 15.12 Absorption (a), CD (b), steady-state fluorescence (c), and exci...

Figure 15.13 The left panel shows CPL spectra obtained at room temperature f...

Figure 15.14 Chemical structures of bis-pyrene-modified peptides that exhibi...

Figure 15.15 Chemical structure of multiple pyrene-modified cyclodextrin tha...

Figure 15.16 (b) Chemical structure, fluorescence quantum yield, and

g

lum

va...

Chapter 16

Figure 16.1 Schematic representation of the molecular arrangement in nematic...

Figure 16.2 Schematic representation of the molecular arrangement in chiral ...

Figure 16.3 Molecular structures of the host N-LCs (PCH302, PCH304, PCH506, ...

Figure 16.4 Polymerization procedures of photo-cross-link polymerization for...

Figure 16.5 Illustration of the formation of the helical network polymer in ...

Figure 16.6 POM images before and after polymerization and SEM images of res...

Figure 16.7 UV–vis absorption and CD spectra of the helical network polymer ...

Figure 16.8 Photoluminescence (PL),

circularly polarized luminescence

(

CPL

),...

Figure 16.9 Molecular structures of the host S

C

-LC (PhB-8 and PhB-10), the c...

Figure 16.10 (a) UV–vis absorption and CD spectra of (

R

)- and (

S

)-system-S

C

*...

Figure 16.11 Schematic images of the (a) photocrosslinking polymerization of...

Figure 16.12 Temperature dependence of the UV–vis absorption, CD, and

g

abs

s...

Figure 16.13 PL, CPL, and

g

lum

spectra of (

R

)- and (

S

)-HNP-S

C

* films before ...

Chapter 17

Figure 17.1 (a) Hypothetical Jablonski diagrams of

L

- and

R

-enantiomers in t...

Figure 17.2 Chemical structures of poly(9,9-di-

n

-octylfluorene) (PF8), poly(

Figure 17.3 Racemization at the ground states of flexible [4]helicene, semi-...

Figure 17.4 LRE in the GS and ES of Eu

III

(dpa)

3

3–

and Eu

III

(cda)

3

6–

...

Figure 17.5 LRE between

P

- and

M

-rotamers of biphenyl and

syn

-/

anti

-bis-fluo...

Figure 17.6 CD-active helical Q1D assemblies from (a) CD-silent tamPcM carry...

Figure 17.7 LRE between

P

- and

M

-rotamers of rhodamine B, Congo red, and twi...

Figure 17.8 Two free Tb

III

ions (green filled circles) embedded into two chi...

Figure 17.9

Λ

/

Δ

-Interconversion of

fac-

/

mer

-Eu(fod)

3

, Eu

III

(...

Figure 17.10 Chirality-/helicity-inducing scaffolds via IMFs to CD-silent ch...

Figure 17.11 Mulliken charges between fod ligand and (1

R

)-

α

-pinene, lea...

Figure 17.12 CD-/CPL-silent helical polysilanes and CD-inactive achiral poly...

Figure 17.13 Left–right equilibrium of rotamers of

π-

conjugated o...

Figure 17.14 One-handed helical

S

-PDMBS with SiH termini, CD-silent helical...

Chapter 18

Figure 18.1 Magnetic circularly polarized luminescence (MCPL) and magnetic c...

Figure 18.2 MCPL (upper panel) and MPL (lower panel) spectra of the pyrene l...

Figure 18.3 MCPL (upper panel) and MPL (lower panel) spectra of the (a) 1-me...

Figure 18.4 MCPL (upper panel) and MPL (lower panel) spectra of [4]helicene ...

Figure 18.5 MCPL (upper panel) and MPL (lower panel) spectra of (a, b) 2-met...

Figure 18.6 MCPL spectra of Eu(III)(hfa)

3

in CHCl

3

under a 1.6 T magnetic fi...

Figure 18.7 MCPL spectra of Tb(III)(hfa)

3

in CHCl

3

(blue line) and acetone (...

Figure 18.8 CPL (black lines, 0.0 T), MCPL [N-up (blue lines) and S-up (red ...

Figure 18.9 MCPL spectra of CdS/ZnS in a PMMA film (blue line) and powder (r...

Figure 18.10 MCPL spectra of CH

5

N

2

PbBr

3

QDs (black) and CsPbBr

3

QDs (gray) i...

Figure 18.11 MCPL spectra of BaMgAl

10

O

17

/Eu(II) (black lines), BaMgAl

10

O

17

/E...

Chapter 19

Figure 19.1 Illustrations of device structures for (a) a typical OLED, (b) a...

Figure 19.2 General structures, representative geometrical isomers, and typi...

Figure 19.3 Representative structures of phosphorescent platinum(II) complex...

Figure 19.4 Strategy to a blue phosphorescent iridium(III) emitter based on ...

Figure 19.5 Structures of Ir(Bzdfppy)

2

(pic) and Ir(Bzdfppy)

3

and their PL sp...

Figure 19.6 Structures of Ir-D-1, Ir-D-2, and Dn and...

Figure 19.7 Structures of red and near-infrared phosphorescent iridium(III) ...

Figure 19.8 EL spectra of OLEDs containing Pt(dbfq)(bdbp) in the emitting la...

Figure 19.9 (a) Structures of Pt(Bzdfppy)(acac), Pt-Dn-1, and Pt...

Figure 19.10 MCPL spectra of Ir(ppy)

3

and Ir(ppy)

2

(acac) in CH

2

Cl

2

and DMSO ...

Figure 19.11 Structures of PtOEP and Pt(dfppy)(acac) and their MCPL spectra ...

Figure 19.12 Illustration of the MCPEL system involving a standard OLED stru...

Figure 19.13 MCPEL (upper panel) and EL (lower panel) spectra of (a) Device-...

Chapter 20

Figure 20.1 Structures of organic derivatives 1 [14], 2 [15], and 3 [16] dis...

Figure 20.2 (a) Schematic structures of the chiral binaphthlene bisimide bui...

Figure 20.3 (a) Structure of 8, a propeller-shape silole functionalized with ...

Figure 20.4 (a) Structure of the achiral soldier and chiral sergeant platinu...

Figure 20.5 (a) Structure of the chiral molecule capable of self-assembly gi...

Figure 20.6 (a) Structure of 27. 27 can form gel from DMF/water mixture. The...

Figure 20.7 (a) Structure of M

+

[Eu(hfbc)

4

]

−.

, in which a Na

+

i...

Figure 20.8 (a) I Structure of the chiral ligands L

1

, L

2

and L

3

, II. Assembl...

Chapter 21

Figure 21.1 Chemical structure of [5]helicene derivatives.

Figure 21.2 Synthesis of 5,10-bis(2,2-dicyanovinyl)[5]helicene derivative 4....

Figure 21.3 Absorption (black) and normalized fluorescence (red) spectra of ...

Figure 21.4 Orbital correlation diagram and composition of the S

1

→S

0

transit...

Figure 21.5 Chemical structures of [7]helicenes and their major CD and CPL t...

Figure 21.6 Orbital correlation diagram and composition of the S

1

→S

0

transit...

Figure 21.7 Synthesis of [7]helicene derivatives.

Figure 21.8 Absorption (black dashed line) and normalized emission (solid li...

Figure 21.9 Theoretically estimated UV-vis absorption (bottom) and CD spectr...

Figure 21.10 Chemical structures and the |

g

CPL

| values of the figure-eight-s...

Figure 21.11 (a) Orbital correlation diagram and transition configurations o...

Figure 21.12 (a) Synthesis and (b) X-ray single crystal structure of 16. One...

Figure 21.13 (a) CD (solid line) and CPL (dashed line) spectra of 16 in chlo...

Chapter 22

Figure 22.1 Chemical structures of chiral

S-/R-

1-10. (The ...

Figure 22.2 (a) Chemical structures of chiral

S-/R-

11. (b) EQE-l...

Figure 22.3 Chemical structures of chiral

S-/R-

13-27. (All...

Figure 22.4 (a) Chemical structures of chiral

S-/R-

25. (b) Struc...

Figure 22.5 (a) Chemical structures of chiral

S-/R-

29. (b) Vacuu...

Figure 22.6 Chemical structures of chiral

S-/R-

31-47 and S...

Figure 22.7 (a) Chemical structures of chiral

S-/R-

48. (b) Devic...

Figure 22.8 Chemical structures of chiral

S-/R-

51-62. (All...

Figure 22.9 (a) Chemical structures of chiral

S-/R-

63-64. ...

Figure 22.10 (a) Chemical structure of chiral

S-/R-

65. (b) Devic...

Figure 22.11 (a) Chemical structures of chiral

S-/R-

67-71....

Figure 22.12 (a) Schematic diagram of the helical alignment of the Ln

3

+

...

Figure 22.13 (a) Size-matched DAEC distributed in the channels and large-siz...

Figure 22.14 (a) The crystal structure of pure chiral two-dimensional (2D) p...

Figure 22.15 (a) Preparing CPL-active chiral helical polymer/perovskite hybr...

Figure 22.16 (a) Schematic illustration of the synthesis and self-resolution...

Figure 22.17 (a) The structure, CD, and CPL spectra of enantiomeric Ag

6

L

6

/D

6

Figure 22.18 (a) The overall structures of

R/S

-Au

3

, SEM and TEM images of

R/

...

Chapter 23

Figure 23.1 Axially chiral naphthalene dimer and tetramer.

Figure 23.2 (a) Chemical structures and optical properties of pyrene-tethere...

Figure 23.3 CPL and structural properties of fluorophore-tethered naphthalen...

Figure 23.4 CPL and structural properties of fluorophore-tethered naphthalen...

Figure 23.5 (a) Chemical structures of binaphthyl–pyrene sandwich dyes 9–10 ...

Figure 23.6 (a) Chemical structure and (b) TD DFT-optimized excited-state st...

Figure 23.7 (a, b) Structural properties of binaphthyl–bipyridyl cyclic dyad...

Figure 23.8 (a) Chemical structures of chiral bipyridyl–ruthenium complexes

Figure 23.9 (a) CPL properties and (TD) DFT-optimized structures of 16 and 1...

Chapter 24

Figure 24.1 Number of publications on CPL from 1980 to November 2022 in SciF...

Figure 24.2 (a) Schematic representation of photo-antenna effect using intra...

Figure 24.3 Ligands for the design of CPL lanthanide complexes. (a) camphore...

Figure 24.4 Electronic absorption and luminescence spectra of polymerization...

Figure 24.5 Selected aromatic ligand inducing polarized luminescence in the ...

Figure 24.6 (a) Magnetic induced circularly polarized luminescence of Eu(III...

Chapter 25

Figure 25.1 (a) Structural motifs for constructing Au

13

(PRP)

5

X

2

NC. (b) Top ...

Figure 25.2 (a) Absorption, (b) CD, (c) PL, and (d) CPL spectra of Ag

29

(DHLA...

Figure 25.3 Structure models of Ag

29

(dithiolate)

12

NCs with a

C

3

-symmetric a...

Figure 25.4 Plots of

g

abs

values (at 500 nm) of Ag

29

(

R

/

S

-DHLA)

12

NCs prepare...

Figure 25.5 Comparison of relative stability of

AC

- and

C

-NC models in the (...

Chapter 26

Figure 26.1 Schematic drawing of chirality of octahedral complexes containin...

Figure 26.2 Structures of 2 and 3. Depending on the stereochemistry of 1,2-d...

Figure 26.3 Reversible Zn complexation of 4 with Zn(OAc)

2

.

Figure 26.4 Heteroleptic (dipyrrinato)Zn(II) complexes 5.

Figure 26.5 Zn complexation to form chiroptical 1-D coordination polymer (

R

/

Figure 26.6 Zn complexation to form optically active dinuclear Zn complex 9....

Figure 26.7 Formation of a chiral homoleptic Zn(II) complex 11.

Figure 26.8 Ring-opened hemiporphyrazine Zn complex 12.

Figure 26.9 Helicene-based

fac

-rhenium(I) complexes.

Figure 26.10 Chiral Cr luminophores with tridentate ligands.

Figure 26.11 Chemical structure of helicene-porphyrin conjugates 26.

Figure 26.12 Chemical structures of porphyrin dimers 27.

Figure 26.13 Chemical structures of oligoamylose-strapped porphyrin 28.

Figure 26.14 Chemical structures of binaphthyl-strapped porphyrins 29 (a) an...

Figure 26.15 Chemical structures of palladium porphyrin linked to chiral lan...

Figure 26.16 Chemical structure of porphyrin 32 with four AIE cyanostilbene ...

Figure 26.17 Chemical structure of tetraanionic porphyrin 33 and the cationi...

Figure 26.18 Self-assembled crystalline CPL materials based on γCD-MOF and a...

Figure 26.19 (a) Illustration of the UC-CPL emission via triplet–triplet ann...

Chapter 27

Figure 27.1 CPL spectra of 22 in dichloromethane.

Figure 27.2 CPL (top) and total emission (bottom) spectra of 52a (left) and

Figure 27.3 CPL spectra of 55 (left) and 56 (right) in tetrahydrofuran.

Figure 27.4 CPL spectra of 57a and 57b in dichloromethane.

Chapter 28

Figure 28.1 Two definitions of the handedness of the same circularly polariz...

Figure 28.2 Structures of

d

-camphorquinone (1) and (

S

,

S

)-trans-β-hydrindanon...

Figure 28.3 Structures of (1

S

,3

R

)-4-methyleneadamantan-2-one (3), (1

S

,3

R

)-4-...

Figure 28.4 Structures of the chiral [2.2.1] bicyclic compounds 1 and 8–10 a...

Figure 28.5 Structures of [6]helicene derivatives, 14–17.

Figure 28.6 Structures of nonsubstituted and substituted [7]helicenes.

Figure 28.7 Structures of [7]helicene-like molecules21–23.

Figure 28.8 Structure of a pyridyl containing heterohelicene24, and its reve...

Figure 28.9 Structures of BODIPY dimers25 and 26.

Figure 28.10 Structures of chiral oligothiophenes27–29.

Figure 28.11 Structures of a

peri

-xanthenoxanthenes30–33.

Figure 28.12 Structure of axially chiral 1,1′-binaphthyls with triethyllsilo...

Figure 28.13 Structures of double-twisted cyclic binaphthyls39–42.

Figure 28.14 †- and ‡-shaped molecules based on [2,2]paracyclophane (

R

p

)-43 ...

Figure 28.15 V-shaped molecules based on [2,2]paracyclophane (

R

p

)-45 and (

S

p

Figure 28.16 V- and X-shaped molecules consisting of five-ringed

para

-phenyl...

Figure 28.17 Structures of π-extended molecules based on [2,2]paracyclophane

Figure 28.18 Structures of a figure-eight-shaped molecule having two [5]heli...

Figure 28.19 Structures of chiral cylindrical molecules56 and 57.

Chapter 29

Figure 29.1 Configuration of CPL measurement system.

Figure 29.2 Optical system for CPL-300.

Figure 29.3 Schematic diagram of monochromator.

Figure 29.4 Wood’s anomalies.

Figure 29.5 Effect of polarization of excitation light on polarization of fl...

Figure 29.6 Relationship between PEM phase difference, and polarization dire...

Figure 29.7 Temporal change in emission intensity.

Figure 29.8 Relationship between electric field vector and degree of ellipti...

Figure 29.9 Schematic diagram of reflection measurement using integrating sp...

Figure 29.10 Diffuse reflectance CD spectrum (top), and LD spectra of (+)/(−...

Figure 29.11 CPL spectra (top) and fluorescence (bottom) spectra of (+)/(−)-...

Figure 29.12 Preparation of KBr pellet sample and measurement setup.

Figure 29.13 CPL and fluorescence spectra of Eu(facam)

3

: (a) KBr method, and...

Figure 29.14 Measurement setup for (a) mull and (b) film samples.

Figure 29.15 (a) CD and LD spectra of binaphthol samples prepared by Nujol m...

Chapter 30

Figure 30.1 Solid-state CD spectra. (a) CD spectra of Δ-1 (1 = [Co(

R,R

-ptn)

3

Figure 30.2 Block diagram of UCS-1.

Figure 30.3 CD spectra of a stretched PVA film dyed with Congo Red measured ...

Figure 30.4 Artifact-free CD and the artifact-free CB satisfy the Kramers–Kr...

Figure 30.5 Block diagram of UCS-2 and UCS-3. Abbreviations are the same as ...

Figure 30.6 DRCD spectra of (

d

) (solid line) and (

l

)-(dotted line) ammonium ...

Figure 30.7 Efficiency curves of DRCD calculated from dc voltages for transm...

Figure 30.8 Block diagram of MC-CD spectrophotometer. (LS) 150 W Xe lamp, (L

Figure 30.9 CD spectrum is obtained by subtracting left-handed from the righ...

Figure 30.10 Transmittance CD and absorption spectra of non-chiral, highly-s...

Figure 30.11 Solid-state CD and absorption spectra of enantiomorphous α-Ni(H

Figure 30.12 Schematic representation of the HAUP/G-HAUP optics with optical...

Figure 30.13 Block diagram of the circularly polarized luminescence spectrop...

Figure 30.14 True CPL, DC and

g

lum

spectra of enantiomeric benzil crystals (...

Figure 30.15 Block diagram of D-CCS; LS; Xe lamp, Mo1: first monochromator, ...

Figure 30.16 (I) CD spectra of a stretched PVA film dyed with Congo red. (a)...

Figure 30.17 Observed CD spectra of the same α-Ni(H

2

O)

6

·SO

4

single crystal (

Figure 30.18 (a) Chiral adduct crystals of Q and PYR, and the DRCD spectra f...

Figure 30.19 CD of hornet silk film after exposure to steam. Representative ...

Figure 30.20 CD spectra of Aβ(1–40) (a) and (1–42) (b) in Tris–HCl buffer (p...

Figure 30.21 (a) Real-time measurement of CD, LD signals, and HV at 230 nm d...

Figure 30.22 Comparison of CHCl

3

solution, KBr-pellet, and PMMA-film dispers...

Chapter 31

Figure 31.1 CD and CPL spectra of a [2.2]paracyclo[2](5,8)quinolinophane der...

Figure 31.2 CPL spectra of two [2.2]paracyclo[2](5,8)quinolinophane derivati...

Figure 31.3 (Left) CPL spectra in forward geometry of syndiotactic polystyre...

Figure 31.4 (Top-left) CPL spectrum (black trace), corrected CPL spectrum (r...

Figure 31.5 CD and CPL spectra of two differently substituted pyreno[

a

]pyren...

Figure 31.6 CD and CPL spectra of tris(2-pyridylmethyl)amine Zinc complex (R...

Figure 31.7 CD and CPL spectra of chiral sulfoxide-containing

ortho

-phenylen...

Figure 31.8 CD and CPL spectra of G-quartet complexes based on the indicated...

Figure 31.9 (Left) CD spectra of (

R

)- and (

S

)-tricarboxamide molecules in me...

Chapter 32

Figure 32.1 Trefoil knot structure of complex 1.

Figure 32.2 (Left) Structures of copper(I) complexes bearing diimine and DIO...

Figure 32.3 Two conformational diastereomers of complex 4.

Figure 32.4 Structures of complexes 5–8. The label X represents O, S, ...

Figure 32.5 (Top) CPL and (bottom) emission spectra of 5, 6, and 7.

Figure 32.6 Three-coordinate copper(I) complexes 9 (R = H) and 10 (R =

t

Bu)....

Figure 32.7 Emissive carbene complexes. 11, R1 =

i

-Pr, R2 = H, R3 = Me, R4 =...

Figure 32.8 Structures of (

P

)-19 (left) and (

M

)-19 (right) complexes.

Figure 32.9 (Top) Structure of [Cu

2

I

2

(

R

-BINAP)] (20). (Bottom) Layered struc...

Figure 32.10 Tetranuclear copper(I) cluster with chiral aminoethylbenzene li...

Figure 32.11 (Left) Structure of the [Cu

5

(S

t

Bu)

6

]

−

anion. (Right) Crys...

Figure 32.12 (Left) Monomer unit and (right) 2D polymer sheet structure of c...

Figure 32.13 Structure of trinuclear copper(I) complex 26. Figure 32.13 show...

Figure 32.14 Copper(I) complex bearing a chiral NHC ligand and an amido liga...

Figure 32.15 Structure of (left) DPM ligands and (right) [Cu

14

(DPM)

8

]

6

+

...

Figure 32.16 Ethynylene-bridged (

S

,

S

)-29

n

molecules (left,

n

 = 1,2,3, and 5)...

Figure 32.17 Ligand of multipodal structure (left) and the metal complexes w...

Figure 32.18 Structure of cluster compound 31. (Left) Top view of cluster pr...

Figure 32.19 Structure of enantiomers of chiral cluster complex 33. The Au

1

A...

Figure 32.20 Structure of gold(I) double salt 34.

Figure 32.21 Homoleptic palladium(0) complexes (35, 36, and 37) with chiral ...

Chapter 33

Figure 33.1 (a) Selection rules for the interband transitions of GaAs; CB, c...

Figure 33.2 Schematic drawing of the device structure of spin-LED, and the s...

Figure 33.3 Chemical structures of chiral Eu complexes and TADF molecules.

Figure 33.4 Chemical structures of F8BT, azahelicene, and

R

5011.

Figure 33.5 Chemical structures of Pt metallomesogen complexes, (

R

/

S

)-BN-CF,...

Figure 33.6 Chemical structures of PDI and PDI derivatives substituted with ...

Figure 33.7 (a) Chemical structures of (

R

,

R

)-/(

S

,

S

)-BPP and (b) the crystal ...

Figure 33.8 Chemical structures of PDI derivative with tris(phenylisoxazolyl...

Figure 33.9 (a) Absorption (black) and fluorescence spectra (gray) of (

S

,

S

)-...

Figure 33.10 (a) Absorption (black) and fluorescence (gray) spectra of the d...

Figure 33.11 (a) CD and CPL (

λ

ex

 = 450 nm) spectra of the thin film and...

Figure 33.12 (a) Optimized molecular structure of the monomer of (

S

,

S

)-BPP a...

Figure 33.13 (a) Schematic drawing of the device structure of CP-OLED based ...

Chapter 34

Scheme 34.1 Molecular structures of (a) Eu(

D

-facam)

3

, (b) ammonium sa...

Figure 34.1 (a) Emission spectra of Eu(

D

-facam)

3

alone and Eu(

D

-facam)

3

/TMA

Figure 34.2 (a) CD (top) and absorption (bottom) spectra of a solution of Eu...

Figure 34.3 (a) Digital photographs of luminescent PMMA/Eu(

D

-facam)

3

and DNA...

Figure 34.4 (a) CD (top) and absorption (bottom) spectra of PMMA/Eu(

D

-facam)

Figure 34.5 (a) Molecular structures of Eu(tta)

3

(H

2

O)

2

, Eu(tta)

3

phen, and Eu...

Chapter 35

Figure 35.1 Electroluminescent exciton dynamic processes of the three genera...

Figure 35.2 OLED structures with single layer and multilayers.

Figure 35.3 Chemical structures of chiral conjugated oligomers and polymers

Figure 35.4 Chemical structures of 9–17 enantiomers.

Figure 35.5 (a) Chemical structures of 18 enantiomers. (b) The model diagram...

Figure 35.6 (a) Chemical structures of 22–24 enantiomers. (b) CPL and CPEL s...

Figure 35.7 Chemical structures of 25–30 enantiomers.

Figure 35.8 Chemical structures of 31–34 enantiomers.

Figure 35.9 Chemical structures of 35–41 enantiomers.

Figure 35.10 Molecule structures of 42–49 enantiomers.

Figure 35.11 Chemical structures of 50–61 enantiomers.

Figure 35.12 Chemical structures of 62 and 63 enantiomers.

Figure 35.13 Chemical structures of 64 and 65 enantiomers.

Figure 35.14 Chemical structures of 66–70 enantiomers.

Figure 35.15 Chemical structures of 71–77 enantiomers.

Chapter 36

Figure 36.1 Schematic illustration representing the underlying processes tha...

Figure 36.2 (a) Schematic representation for the equilibrium between

s-cis

...

Figure 36.3 (a) Illustration of inversion and switching of CPL regulated by ...

Figure 36.4 (a) Schematic illustration of coassembly of 4 with achiral couma...

Figure 36.5 (a) Coordination mode of 5 and Zn

2+

weakening the H-bonding ...

Figure 36.6 (a) Photoisomerization of 6. A mixture of

E,E

;

E,Z

and

Z,Z

isome...

Figure 36.7 (a) Molecular structure of 7 showing

Z–E

isomerization und...

Figure 36.8 (a) Photoisomerization process of 8. (b) Schematic illustration ...

Figure 36.9 (a) Reversible isomerization process of 9 induced by two lights ...

Figure 36.10 (a) Reversible photo-driven chiral inversion of molecular motor...

Figure 36.11 (a) Self-assembly of 11 and coassembly of 11 with a chiral fluo...

Figure 36.12 (a) The formation of radical anions of 12 upon UV irradiation.

Figure 36.13 (a) Chemical structure of 13 (b) UV/Vis absorption spectra, (c)...

Figure 36.14 (a) Chemical structure of 14. CPL (top) and fluorescence (botto...

Figure 36.15 (a) Chemical structures of 17–20. (b) The

g

em

(filled cir...

Figure 36.16 (a) Chemical structures of 21a–f. (b) Chemical structures...

Figure 36.17 (a) Illustration of the bio-inspired proton shuttle strategy of...

Figure 36.18 Chemical structures of 27–31.

Figure 36.19 (a) (i) Jablonski diagram explaining the change of the CPL hand...

Figure 36.20 Schematic illustration of the process of coassembly of 37 with ...

Figure 36.21 (a) Chemical Structures of 38 and 39. (b) Schematic illustratio...

Figure 36.22 (a) Structures of gelator polymer 40 and Rhodamine B. (b) CPL of...

Figure 36.23 (a) Schematic illustration of CW and CCW stirring-induced rearr...

Figure 36.24 (a) Chemical structures of 41 and 42. (b)

g

PL

as a function of ...

Chapter 37

Figure 37.1 Schematic diagram of OLED with antireflection film to illustrate...

Figure 37.2 Efficiency enhancement of the OLED as a function of the dissymme...

Figure 37.3 (a) The schematic diagram of OLED structure and energy levels fo...

Figure 37.4 (a) CPEL spectra for the pure F8BT film (

d

 = 200 nm) without dop...

Figure 37.5 Schematic diagrams of the twisted stacking of rigid rods describ...

Figure 37.6 Experimental results of

g

PL

(represented by symbols) as a functi...

Figure 37.7 (a) Contour map of the calculated

g

EL

as a function of the twist...

Figure 37.8 Schematic diagrams of the fabrication process. (a) The first rub...

Figure 37.9 EL spectra and

g

-factors. (a)–(c) EL spectra for various twisted...

Figure 37.10 The orthogonal CPPL and CPEL from a single EML. (a) Schematic d...

Figure 37.11 Chemical structures and energy levels. The chemical structures ...

Figure 37.12 Schematic diagram of EL sample and characteristics of CP light....

Chapter 38

Figure 38.1 Correlation of Δ

H

, Δ

S

,

K,

and temperature according to the van’t...

Figure 38.2 Representative binding model of multiple binding host with guest...

Figure 38.3 Correlation between stoichiometry (

a

,

b

) and

x

-coordinate at the...

Figure 38.4 Representative example of host–guest complexation: (a) with colo...

Figure 38.5 Representative UV–visible spectra to show correlation of observe...

Figure 38.6 Graphical expression showing exemplified ways (a)–(e) to change ...

Figure 38.7 The correlation between complexation ratio (

x

) and binding const...

Figure 38.8 The correlation between complexation ratio (

x

) and binding const...

Figure 38.9 The calculated curves plotted between [

G

]

0

/[

H

]

0

and [

C

]/[

H

]

0

use...

Figure 38.10 Useful graph for [

G

]

0

range determination of titration experime...

Figure 38.11 Spreadsheet for statistical data-treatment based on Students

t

-...

Guide

Cover

Table of Contents

Title Page

Copyright

Preface

Acknowledgments

Section I Molecules

Begin Reading

Index

End User License Agreement

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