Polycyclic Arenes and Heteroarenes E-Book

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

Seitenzahl: 556

Veröffentlichungsjahr: 2015

Beschreibung

The first book of its kind to focus on the chemistry of this promising class of molecules. Edited by an innovator in the field, who has gathered an international team of well-established experts, this is a comprehensive overview of the rapidly developing field of polycyclic (hetero)arenes, specifically highlighting on their molecular design and the latest synthetic procedures, as well as chemical and physical properties. Each chapter is dedicated to a specific compound class, the first eight covering polycyclic arenes, including both planar and non-planar conjugated molecules, while chapters nine to twelve deal with polycylic heteroarenes according to the heteroatoms, namely N, B, S and P. Important current and emergent applications in the field are also discussed, ranging from molecular sensors to electronic devices. The result is an essential reference for researchers in synthetic and physical organic chemistry, supramolecular chemistry, and materials science.

Leseprobe

Table of Contents

Cover

Related Titles

Title Page

Copyright

Preface

References

List of Contributors

Part I: Polycyclic Arenes

Chapter 1: Open-Shell Benzenoid Polycyclic Hydrocarbons

1.1 Introduction

1.2 Higher Order Acenes

1.3 Phenalenyl-Based Diradicaloids

1.4 Anthenes and Periacenes

1.5

π

-Extended

p

-Quinodimethane

1.6 Triangulene-Based Triplet Biradicals

1.7 Potential Applications

1.8 Conclusion

References

Chapter 2: Planar Cyclopenta-Fused Polycyclic Arenes

2.1 Introduction

2.2 Acenaphthylenes

2.3 Dibenzopentalenes

2.4 Indenofluorenes

2.5 Conclusions

Acknowledgment

References

Chapter 3: Growing Buckybowl Chemistry

3.1 Introduction

3.2 π-Extended Buckybowls

3.3 Chiral Buckybowl

3.4 Heterobuckybowl

3.5 Columnar Crystal Packing of Buckybowls

3.6 Summary and Conclusions

References

Chapter 4: Polycyclic Arenes Containing Seven-Membered Carbocycles

4.1 Introduction

4.2 Azulene, Oligo-azulenes, and Fused Azulenes

4.3 Polycyclic Arenes Containing 5

H

-Dibenzo[

a

,

d

]cycloheptene Units

4.4 Cyclohepta[

de

]naphthalene, dicyclohepta[

de

,

ij

]naphthalene, and Their Benzannulated Derivatives

4.5 Curved Polycyclic Arenes Containing Highly Fused Cycloheptatriene

4.6 Conclusions

Acknowledgment

References

Chapter 5: Polycyclic Arenes Containing Eight-Membered Carbocycles

5.1 Introduction

5.2 [8]Annulenes

5.3 Tetraphenylenes

5.4 [8]Circulene

5.5 Concluding Remarks

References

Chapter 6: Cycloparaphenylenes and Carbon Nanorings

6.1 Introduction

6.2 Early Developments

6.3 Strain and HOMO/LUMO Energies of CPPs

6.4 Synthesis of CPPs

6.5 Properties of CPPs

6.6 Summary and Conclusions

References

Chapter 7: Advances in Chemistry of Dehydrobenzoannulenes

7.1 Introduction

7.2 Synthesis and Properties of New DBAs

7.3 DBAs as Graphyne and Graphdiyne Motifs

7.4 DBAs as Supramolecular Building Blocks

7.5 DBAs in Optoelectronic Applications

7.6 DBAs as Synthetic Precursors

7.7 Summary and Conclusions

References

Chapter 8: Tetraarylethenes and Aggregation-Induced Emission

8.1 Introduction

8.2 Fundamentals

8.3 Applications

8.4 Outlook

References

Part II: Polycyclic Heteroarenes

Chapter 9: N-Containing Polycyclic Heteroarenes

9.1 Introduction

9.2 Linear and Extended

N

-Heteroarenes

9.3 Nitrogen-Rich Macrocyclic Arenes

9.4 Miscellaneous

9.5 Summary and Conclusion

References

Chapter 10: Boron-Containing Polycyclic Aromatics

10.1 Introduction

10.2 Historical Perspective and Representative Structures

10.3 General Synthetic Strategies

10.4 Recent Developments in

B

-PAH Structures and Properties

10.5 Conclusions/Outlook

References

Chapter 11: S-Containing Polycyclic Heteroarenes: Thiophene-Fused and Thiadiazole-Fused Arenes as Organic Semiconductors

11.1 Introduction

11.2 Electronic Structures of Fused Thiophenes and Thiadiazoles

11.3 p-Type Semiconductors with Fused Thiophenes

11.4 n-Type Semiconductors with Fused Thiophenes

11.5 Thiadiazole Derivatives

11.6 Summary and Conclusions

References

Chapter 12: P-Containing Heteroarenes: Synthesis, Properties, Applications

12.1 Introduction

12.2 Five-Membered Ring Systems

12.3 Six-Membered Ring Systems

12.4 Seven-Membered Ring Systems

12.5 Other Phosphorus-Containing Diketo-Ring Systems

12.6 Summary and Conclusions

Acknowledgments

References

Index

End User License Agreement

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Guide

Cover

Table of Contents

Preface

Part I: Polycyclic Arenes

Begin Reading

List of Illustrations

Chapter 1: Open-Shell Benzenoid Polycyclic Hydrocarbons

Figure 1.1 Molecular graphenes by fusion of benzene rings in different modes.

Figure 1.2 Resonance forms of pentacene

11.

Figure 1.3 Nonacene derivatives. (ESR spectra of

26

is adapted with permission from Ref. [27]. Copyright 2011, John Wiley and Sons.)

Figure 1.4 (a) Resonance forms of bis(phenalenyls) with different aromatic linkers. (b) Crystal structure of

28d

. (Adapted with permission from Ref. [33]. Copyright 2005, John Wiley and Sons.) (c) Crystal structure of

31b

. (Adapted with permission from Ref. [36]. Copyright 2004, John Wiley and Sons.) (d) Intra and intermolecular covalent bonding interactions in a schematic 1D stack of

30a (

blue and orange dotted lines). (Adapted with permission from Ref. [35]. Copyright 2012, Royal Society of Chemistry.)

Figure 1.5 (a) Resonance structures of radical

33

. (b) Single-crystal structures of

33b

. (Adapted with permission from Ref. [39]. Copyright 2011, American Chemical Society.) (c) Structure of trisphenalenyl radical

34

. (d) Cyclic voltammogram of

34b

. (Adapted with permission from Ref. [6]. Copyright 2014, John Wiley and Sons.)

Figure 1.6 Resonance structures of zethrene and higher order zethrenes.

Figure 1.7 Synthesis of zethrene derivatives.

Figure 1.8 Heptazethrene and octazethrene derivatives. (Crystal Figure are adapted with permission from Ref. [49]. Copyright 2012, American Chemical Society.)

Figure 1.9 Exercise of Clar's sextet rule in isomeric dibenzoheptazethrene systems.

Figure 1.10

p

-QDM bridged perylene dimers.

Figure 1.11 A persistent triplet biradical based on isomeric heptazethrene.

Figure 1.12 Structures of anthenes.

Figure 1.13 Syntheses of teranthene and quarteranthene derivatives.

Figure 1.14 Structures of periacenes.

Figure 1.15 Preliminary studies toward the synthesis of peripentacene.

Figure 1.16 Parent

p

-QDM and its derivative.

Figure 1.17 Tetrabenzo-Tschitschibabin's hydrocarbons.

Figure 1.18 Tetracyano-N-annulated perylene quinodimethanes.

Figure 1.19 Fused tetracyano-N-annulated rylene quinodimethanes.

Figure 1.20 Tetracyanothiophene-capped N-annulated perylene quinodimethanes.

Figure 1.21 Synthetic route to tri-

tert

-butyl triangulene biradical

113

and its characterization by variable-temperature ESR spectroscopy. (Adapted with permission from Ref. [71]. Copyright 2001, American Chemical Society.)

Figure 1.22 Synthesis of the biradical trianion

117

.

Chapter 2: Planar Cyclopenta-Fused Polycyclic Arenes

Figure 2.1 Selected cyclopenta-fused polycyclic arenes with subunit in bold: (a) Cyclopent[]aceanthrylene, (b) dibenzopentalene, and (c) indeno[1,2-]fluorene.