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Tomas Torres

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Discover a new generation of organic nanomaterials and their applications Recent developments in nanoscience and nanotechnology have given rise to a new generation of functional organic nanomaterials with controlled morphology and well-defined properties, which enable a broad range of useful applications. This book explores some of the most important of these organic nanomaterials, describing how they are synthesized and characterized. Moreover, the book explains how researchers have incorporated organic nanomaterials into devices for real-world applications. Featuring contributions from an international team of leading nanoscientists, Organic Nanomaterials is divided into five parts: * Part One introduces the fundamentals of nanomaterials and self-assembled nanostructures * Part Two examines carbon nanostructures--from fullerenes to carbon nanotubes to graphene--reporting on properties, theoretical studies, and applications * Part Three investigates key aspects of some inorganic materials, self-assembled monolayers, organic field effect transistors, and molecular self-assembly at solid surfaces * Part Four explores topics that involve both biological aspects and nanomaterials such as biofunctionalized surfaces * Part Five offers detailed examples of how organic nanomaterials enhance sensors and molecular photovoltaics Most of the chapters end with a summary highlighting the key points. References at the end of each chapter guide readers to the growing body of original research reports and reviews in the field. Reflecting the interdisciplinary nature of organic nanomaterials, this book is recommended for researchers in chemistry, physics, materials science, polymer science, and chemical and materials engineering. All readers will learn the principles of synthesizing and characterizing new organic nanomaterials in order to support a broad range of exciting new applications.

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Contents

Cover

Title Page

Copyright

Preface

Contributors

Chapter 1: A Proposed Taxonomy and Classification Strategy for Well-Defined, Soft-Matter Nanoscale Building Blocks

1.1 INTRODUCTION

1.2 ADAPTATION OF LINNAEAN TAXONOMY PRINCIPLES TO A NEW NANO-CLASSIFICATION SCHEME

1.3 HOW DOES NATURE TRANSFER STRUCTURAL INFORMATION FROM A LOWER HIERARCHICAL LEVEL TO HIGHER COMPLEXITY?

1.4 THE USE OF CLADOGRAMS FOR CLASSIFICATIONS OF WELL-DEFINED BIOLOGICAL (MICRON SCALE/MACROSCALE), ATOMIC (PICOSCALE), AND NANOSCALE BUILDING BLOCKS

1.5 HEURISTIC MAGIC NUMBER MIMICRY AT THE SUBATOMIC, ATOMIC, AND NANOSCALE LEVELS

1.6 ELEMENT CATEGORIES AND THEIR HYBRIDIZATION INTO NANO-COMPOUNDS AND NANO-ASSEMBLIES

1.7 A NANO-PERIODIC SYSTEM FOR DEFINING AND UNIFYING NANOSCIENCE

1.8 CHEMICAL BOND FORMATION/VALENCY AND STOICHIOMETRIC BINDING RATIOS WITH DENDRIMERS TO FORM NANO-COMPOUNDS

1.9 PROPOSED LINNAEAN-TYPE TAXONOMY FOR SOFT-MATTER-TYPE NANO-ELEMENT CATEGORIES, THEIR COMPOUNDS AND ASSEMBLIES

1.10 CONCLUSIONS

ACKNOWLEDGMENTS

REFERENCES

Chapter 2: On the Role of Hydrogen-Bonding in the Nanoscale Organization of π-Conjugated Materials

2.1 INTRODUCTION

2.2 H-BONDING ALONG THE STACKING POLYMER AXIS

2.3 H-BONDING PERPENDICULAR TO THE STACKING POLYMER AXIS

2.4 MAIN-CHAIN H-BONDED π-FUNCTIONAL POLYMERS

2.5 CONCLUSIONS

ACKNOWLEDGMENTS

REFERENCES

Chapter 3: Chiral Organic Nanomaterials

3.1 INTRODUCTION

3.2 STRUCTURAL AND MECHANISTIC FACTORS IN THE GROWTH OF CHIRAL STRUCTURES

3.3 SINGLE MOLECULE CHIRAL MATERIALS

3.4 CHIRAL ORGANIC NANOPARTICLES

3.5 CHIRAL FIBERS

3.6 CHIRAL NANOTUBES

3.7 CHIRAL MONOLAYERS

3.8 CHIRAL FILMS

3.9 CHIRAL POLYMERS

3.10 CHIRAL NANOPOROUS SOLIDS

3.11 CONCLUDING REMARKS

ACKNOWLEDGMENTS

REFERENCES

Chapter 4: Biochemical Nanomaterials Based on Poly(ε-Caprolactone)

4.1 INTRODUCTION

4.2 LIVING POLYMERIZATION OF ε-CAPROLACTONE

4.3 COPOLYMERS WITH POLY(ɛ-CAPROLACTONE)

4.4 HETEROBIFUNCTIONAL PCL-DERIVED NANOMATERIALS

4.5 CONCLUSIONS AND OUTLOOK

ACRONYMS AND ABBREVIATIONS

REFERENCES

Chapter 5: Self-Assembled Porphyrin Nanostructures and their Potential Applications

5.1 INTRODUCTION

5.2 SYNTHESIS AND STRUCTURE

5.3 OPTICAL, ELECTRONIC, AND PHOTOCATALYTIC PROPERTIES

5.4 APPLICATIONS OF PORPHYRIN NANOSTRUCTURES AND NANOCOMPOSITES TO THE GENERATION, STORAGE, AND UTILIZATION OF SOLAR ENERGY

5.5 FUTURE DIRECTIONS AND CONCLUSIONS

ACRONYMS

ACKNOWLEDGMENTS

REFERENCES

Chapter 6: Nanostructures and Electron-Transfer Functions of Nonplanar Porphyrins

6.1 INTRODUCTION

6.2 INTERMOLECULAR PHOTOINDUCED ELECTRON TRANSFER OF NONPLANAR PORPHYRINS

6.3 PHOTOINDUCED ELECTRON TRANSFER IN SUPRAMOLECULAR COMPLEXES OF NONPLANAR PORPHYRINS

6.4 SUPRAMOLECULAR CONGLOMERATE COMPOSED OF SADDLE-DISTORTED ZINC(II)-PHTHALOCYANINE AND H4DPP2+

6.5 NONPLANAR PORPHYRIN NANOCHANNELS

6.6 PHOTOCONDUCTIVITY OF PORPHYRIN NANOCHANNELS

6.7 SUMMARY AND CONCLUSIONS

ACKNOWLEDGMENTS

REFERENCES

Chapter 7: Tweezers and macrocycles for the molecular recognition of fullerenes

7.1 INTRODUCTION

7.2 PORPHYRIN-BASED MOLECULAR TWEEZERS AND MACROCYCLES

7.3 FULLY ORGANIC MOLECULAR TWEEZERS AND MACROCYCLES

7.4 CONCLUSIONS AND OUTLOOK

REFERENCES AND NOTES

Chapter 8: Covalent, Donor–Acceptor Ensembles based ON Phthalocyanines AND CARBON Nanostructures

8.1 INTRODUCTION

8.2 DONOR–ACCEPTOR, COVALENTLY LINKED PHTHALOCYANINE–FULLERENE SYSTEMS

8.3 PHTHALOCYANINE–C60 COVALENT SYSTEMS PRESENTING LONG-RANGE ORDER

8.4 COVALENTLY LINKED PHTHALOCYANINE–CARBON NANOTUBE ENSEMBLES

8.5 PHTHALOCYANINE–GRAPHENE ENSEMBLES

8.6 CONCLUSIONS AND OUTLOOK

ACKNOWLEDGMENTS

REFERENCES

Chapter 9: Photoinduced Electron Transfer of Supramolecular Carbon Nanotube Materials Decorated with Photoactive Sensitizers

9.1 INTRODUCTION

9.2 MODULATING ELECTRON TRANSFER PATH IN DIAMETER-SORTED SWCNTs

9.3 COVALENTLY LINKED ARCHITECTURES

9.4 DOUBLE-DECKER ARCHITECTURES VIA π–π STACKING AND COVALENT BONDING

9.5 TRIPLE-DECKER ARCHITECTURES VIA π–π STACKING AND COORDINATION BOND FORMATION

9.6 TRIPLE-DECKER ARCHITECTURES VIA π–π STACKING AND ION-PAIR INTERACTIONS

9.7 TRIPLE-DECKER ARCHITECTURES VIA π–π STACKING AND CROWN ETHER INCLUSION COMPLEX FORMATION

9.8 DENDRIMER ARCHITECTURE

9.9 SUMMARY

ACKNOWLEDGMENTS

REFERENCES

Chapter 10: Interfacing Porphyrins/Phthalocyanines with Carbon Nanotubes

10.1 INTRODUCTION

10.2 RESULTS AND DISCUSSIONS

10.3 OUTLOOK

REFERENCES

Chapter 11: Organic Synthesis of Endohedral Fullerenes Encapsulating Helium, Dihydrogen, and Water

11.1 INTRODUCTION

11.2 HOW WE STARTED THE RESEARCH—REACTIONS OF C60 WITH POLYAZA-AROMATICS

11.3 ENDOHEDRAL C60 ENCAPSULATING DIHYDROGEN, H2@C60

11.4 ENDOHEDRAL C70 ENCAPSULATING DIHYDROGEN, H2@C70 AND (H2)2@C70

11.5 ENDOHEDRAL FULLERENES ENCAPSULATING HELIUM, He@C60 AND He@C70

11.6 SPIN CHEMISTRY

11.7 SYNTHESIS AND PROPERTIES OF H2O@C60

11.8 APPLICATION OF OPEN-CAGE FULLERENES TO ORGANIC SOLAR CELLS

11.9 OUTLOOK

REFERENCES

Chapter 12: Fundamental and Applied Aspects of Endohedral Metallofullerenes as Promising Carbon Nanomaterials

12.1 INTRODUCTION

12.2 SYNTHESIS, SEPARATION, AND PURIFICATION OF EMFs

12.3 STRUCTURE ELUCIDATION OF EMFs

12.4 ELECTRONIC PROPERTIES

12.5 CHEMICAL REACTIVITY

12.6 CONTROL OF DYNAMIC MOTION OF METAL ATOMS IN FULLERENE CAGES

12.7 ELECTRONIC MODULATION OF EMFs BY EXOHEDRAL CHEMICAL FUNCTIONALIZATION

12.8 MISSING EMFs

12.9 METAL CARBIDE EMFs: STRUCTURES AND CHEMISTRY

12.10 SYNTHESIS AND PHOTOPHYSICS OF EMF-BASED DYADS

12.11 EMFs AS ACTIVE COMPONENTS IN ORGANIC SOLAR CELLS

12.12 CARRIER TRANSPORT PROPERTIES OF EMFs

12.13 CONCLUSION

REFERENCES

Chapter 13: An update on electrochemical characterization and potential applications of carbon materials

13.1 INTRODUCTION

13.2 PRISTINE FULLERENES

13.3 ENDOHEDRAL FULLERENES

13.4 ELECTROSYNTHESIS OF C60 AND C70 FULLERENE DERIVATIVES

13.5 CARBON NANO-ONIONS (CNOs)

13.6 FULLERENE-BASED COMPOUNDS FOR POTENTIAL PHOTOVOLTAIC APPLICATIONS

13.7 SUMMARY AND OUTLOOK

REFERENCES

Chapter 14: Solvating Insoluble Carbon Nanostructures by Molecular Dynamics

14.1 CNT IN LIQUIDS

14.2 NONCOVALENT FUNCTIONALIZATION OF CNTs

14.3 CONCLUSION

REFERENCES

Chapter 15: Inorganic Capsules: Redox-Active Guests in Metal Cages

15.1 INTRODUCTION

15.2 POLYOXOMETALATES

15.3 THE WELLS–DAWSON CLUSTER [X2M18O62]N−

15.4 THE KEGGIN CLUSTER

15.5 CONCLUSION

REFERENCES

Chapter 16: Stimuli-Responsive Monolayers

16.1 INTRODUCTION

16.2 LIGHT-RESPONSIVE MONOLAYERS

16.3 TEMPERATURE-RESPONSIVE LAYERS

16.4 PH-RESPONSIVE MONOLAYERS

16.5 ELECTROCHEMICALLY RESPONSIVE MONOLAYERS

16.6 MULTI-RESPONSIVE MONOLAYERS

16.7 CONCLUSIONS AND FUTURE PERSPECTIVES

REFERENCES

Chapter 17: Self-Assembled Monolayers as Model Biosurfaces

17.1 INTRODUCTION

17.2 ORGANIC MONOLAYER FILMS

17.3 SELF-ASSEMBLED MONOLAYERS

17.4 BIOLOGICAL SURFACES

17.5 CONCLUSIONS

REFERENCES

Chapter 18: Low-Dimensionality Effects in Organic Field Effect Transistors

18.1 INTRODUCTION

18.2 PHENOMENOLOGICAL DESCRIPTION OF OFETs

18.3 OFET FABRICATION

18.4 CHARGE INJECTION IN OFETs: THE ORGANIC–METAL INTERFACE

18.5 LOW-DIMENSIONAL CHARGE TRANSPORT IN OFETs: DIELECTRIC/ORGANIC AND ORGANIC/ORGANIC INTERFACES

18.6 COUPLING THE CHANNEL TO AMBIENT: SENSING PRINCIPLES AND APPLICATIONS

18.7 CONCLUSION AND OUTLOOK

REFERENCES

Chapter 19: The Growth of Organic Nanomaterials by Molecular Self-Assembly at Solid Surfaces

19.1 INTRODUCTION: MOLECULAR SELF-ASSEMBLY

19.2 LIGHT-HARVESTING SYSTEMS: ZN-TMP/CU(100)

19.3 OPTIMIZED GEOMETRIES FOR BULK HETEROJUNCTIONS SOLAR CELLS: PCBM–EXTTF/AU(111)

19.4 ORGANIC NANOCRYSTALS: SUBPC/CU(111)

19.5 CONCLUSIONS AND OUTLOOK

ACKNOWLEDGMENTS

REFERENCES

Chapter 20: Biofunctionalized Surfaces

20.1 INTRODUCTION

20.2 ASSEMBLING BIOLOGICAL MATERIALS ON INORGANIC SURFACES

20.3 SURFACE PATTERNING

20.4 SOME EXAMPLES

REFERENCES

Chapter 21: Carbon nanotube derivatives as anticancer drug delivery systems

21.1 INTRODUCTION

21.2 CNT FUNCTIONALIZATION

21.3 NONCOVALENT FUNCTIONALIZATION

21.4 COVALENT FUNCTIONALIZATION

21.5 CNT TOXICITY

21.6 CNT AS DELIVERY SYSTEM FOR CANCER

21.7 UPTAKE MECHANISM

21.8 DELIVERY OF ANTINEOPLASTIC CHEMOTHERAPEUTIC DRUGS

21.9 CONCLUSIONS

REFERENCES

Chapter 22: Porous nanomaterials for biomedical applications

22.1 INTRODUCTION

22.2 MICRO- AND MESOPOROUS MATERIALS MEETS BIOLOGY

22.3 IN VITRO STUDIES: INTERACTION OF ZEOLITES AND MESOPOROUS MATERIALS WITH CELLS

22.4 IN VIVO STUDIES: IMAGING AND DRUG DELIVERY

22.5 SELF-ASSEMBLY OF ZEOLITES INTO ORDERED MONOLAYERS

22.6 FUNCTIONALIZATION OF ZEOLITE MONOLAYERS

REFERENCES

Chapter 23: Dicationic gemini nanoparticle design for gene therapy

23.1 GENE THERAPY AND CHALLENGES

23.2 GEMINI SURFACTANTS AS NOVEL BIOMATERIALS

23.3 RATIONAL DESIGN OF GEMINI NANOPARTICLES

23.4 CHARACTERIZATION OF GEMINI NANOPARTICLES

23.5 TRANSFECTION PROPERTIES— STRUCTURE–ACTIVITY IN VITRO STUDIES

23.6 IN VIVO STUDIES

23.7 NANOPARTICLE DESIGN FOR SUBCELLULAR INTELLIGENCE

23.8 SUMMARY

ACKNOWLEDGMENTS

REFERENCES

Chapter 24: Sensing Hg(II) Ions in Water: From Molecules to Nanostructured Molecular Materials

24.1 INTRODUCTION

24.2 Hg(II) RESPONSIVE SMALL-MOLECULE RECEPTORS

24.3 NANOSTRUCTURED MOLECULAR MATERIALS AS Hg(II) SENSORS

24.4 SUMMARY

REFERENCES

Chapter 25: Organic nanomaterials for efficient bulk heterojunction solar cells

25.1 INTRODUCTION

25.2 MAJOR TRENDS IN THE DESIGN OF NOVEL PHOTOACTIVE MATERIALS FOR BULK HETEROJUNCTION SOLAR CELLS

25.3 ACTIVE LAYER NANOMORPHOLOGY AS A MAJOR FACTOR LIMITING PHOTOVOLTAIC PERFORMANCE OF BULK HETEROJUNCTION SOLAR CELLS

25.4 ADVANCED ELECTRON ACCEPTOR MATERIALS FOR BULK HETEROJUNCTION SOLAR CELLS

25.5 ADVANCED ELECTRON DONOR MATERIALS FOR BULK HETEROJUNCTION SOLAR CELLS

25.6 CONCLUSION AND OUTLOOK

ACKNOWLEDGMENTS

REFERENCES

Chapter 26: Mesoscopic Dye-Sensitized Solar Cells

26.1 INTRODUCTION

26.2 MESOSCOPIC NANOMATERIALS

26.3 MOLECULAR ABSORBERS

26.4 REDOX MEDIATORS

26.5 COUNTERELECTRODE

26.6 CONCLUSIONS

REFERENCES

Index

Copyright © 2013 by John Wiley & Sons, Inc. All rights reserved.

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Library of Congress Cataloging-in-Publication Data

Organic nanomaterials : synthesis, characterization, and device applications / [edited by] Tomas Torres, Giovanni Bottari. pages cm Includes index. ISBN 978-1-118-01601-5 (hardback) 1. Organic compounds--Synthesis. 2. Nanostructured materials. I. Torres, Tomas, editor of compilation. II. Bottari, Giovanni, editor of compilation. QD262.O64 2013 620.1′17–dc23 2013000335

PREFACE

In the last decade, much progress has been made in the field of organic nanomaterials. Recent developments in nanoscience and nanotechnology have driven this field forward, thus allowing the preparation of novel materials with controlled morphology and well-defined properties, with clear and exciting technological applications. The new insights into the optoelectronic properties of molecules, together with the recent development of techniques such as scanning probe microscopy, among many others, have pushed chemists to design novel molecular and supramolecular functional architectures. The implications range from the basic molecular self-assembly of complementary organic systems, which constitute an important part of the so-called “bottom-up approach” to exciting new applications of pure organic or hybrid materials, like the ones expected for low dimensional carbon nanostructures, such as fullerenes, nanotubes, and graphenes, or the recent developments in molecular photovoltaics, for example, in nanostructured hybrid materials for energy conversion and storage. The aim of this book entitled Organic Nanomaterials: Synthesis, Characterization, and Device Applications, is to present an appropriate and representative coverage of these materials, which constitute one of the most actively pursued fields of science.

This book contains 26 chapters, which have been rationally organized in five main parts. The first part is concerned with introductory and general chapters on nanomaterials and self-assembled nanostructures. Christensen and Tomalia propose a classification strategy for well-defined, soft-matter nanoscale building blocks (Chapter 1), Schenning and González-Rodríguez analyze the role of hydrogen bonding in the nanoscale organization of π-conjugated materials (Chapter 2), and Amabilino reviews some interesting aspects of chiral, organic nanomaterials (Chapter 3). An overview of a class of biochemical nanomaterials is given by Javakhishvili and Hvilsted (Chapter 4), followed by thorough studies of self-assembled porphyrin nanostructures and their potential applications by Shelnutt and Medforth (Chapter 5); finally, electron-transfer functions of nonplanar porphyrins are studied by Fukuzumi and Kojima (Chapter 6).

The second part of the book consists of a series of chapters devoted to carbon nanostructures ranging from fullerenes (including endohedral fullerenes) and carbon nanotubes to graphene, which report on properties, theoretical studies, and applications. The supramolecular aspects of receptors for the molecular recognition of fullerenes are described by Canevet, Pérez, and Martín (Chapter 7), whereas covalent, donor–acceptor ensembles based on phthalocyanines and carbon nanostructures, including graphene, are reviewed by Bottari, Urbani, and Torres (Chapter 8). Breakthroughs in the photophysics of carbon nanotubes are covered by two excellent contributions addressing (a) the photoinduced electron-transfer properties of supramolecular carbon nanotube materials decorated with photoactive sensitizers, outlined by D'Souza, Sandanayaka, and Ito (Chapter 9), and (b) the study of the interactions of porphyrins and phthalocyanines with carbon nanotubes, which is presented by Bartelmeß and Guldi (Chapter 10). The next two chapters are dedicated to endohedral fullerenes, namely to the synthesis of systems encapsulating helium, dihydrogen, and water, by Murata, Murata, and Komatsu (Chapter 11), and to fundamental and applied aspects of endohedral metallofullerenes by Akasaka and co-workers (Chapter 12). In these two interesting chapters, the authors present new insights into the chemistry and properties of endohedral fullerenes. This block of the book mainly devoted to carbon nanostructures is closed with an excellent update on electrochemical characterization and potential applications of carbon materials by Echegoyen and co-workers (Chapter 13), followed by a theoretical approach to solvating insoluble carbon nanostructures by molecular dynamics by Calvaresi and Zerbetto (Chapter 14).

The third group of chapters focuses on different aspects of some inorganic materials, self-assembled monolayers, organic field effect transistors, and molecular self-assembly at solid surfaces. Thus, the topic of inorganic metal capsules with redox-active guests is treated by Macdonell and Cronin (Chapter 15), whereas the following two chapters developed by Huskens and co-workers (Chapter 16) and by Laromaine and Mace (Chapter 17) review the use of stimuli-responsive monolayers and self-assembled monolayers as model biosurfaces, respectively. Finally, the low- dimensionality effects in organic field effect are described by Biscarini and co-workers (Chapter 18), and the block is well-complemented by the growth of organic nanomaterials by molecular self-assembly at solid surfaces, which is developed by Gallego, Otero, and Miranda (Chapter 19).

The fourth part of the book consists of a series of chapters dealing with different areas involving both biological aspects and nanomaterials. In this part, Vélez reports on the interesting area of biofunctionalized surfaces (Chapter 20), whereas Fabbro, Da Ros, and Prato describe carbon nanotube derivatives as anticancer drug delivery systems (Chapter 21), with a special attention to the medical applications of different kinds of carbon nanotube-based nanomaterials. Closing this section, a study on porous nanomaterials for biomedical applications is outlined by De Cola and co-workers (Chapter 22), whereas Foldvari and co-workers report on nanoparticle design for gene therapy (Chapter 23).

The book ends with three comprehensive applied chapters, as examples of the potential use of organic nanostructured materials in nanoscience, which are devoted to sensors and molecular photovoltaics. This part starts with a chapter by Ratera, Tárraga, Molina, and Vecianna which discusses the sensing of Hg(II) ions in water (Chapter 24), and it is followed by two chapters on the main fields of organic solar cells, namely, organic nanomaterials for efficient bulk heterojunctions by Troshin and Sariciftci (Chapter 25), and mesoscopic dye-sensitized solar cells by Nazeeruddin, Ko, and Grätzel (Chapter 26).

Most chapters end with a summarizing conclusion that also serves as an abstract. The combined authors of the chapters give a good representation of the organic nanomaterials, although with different styles as is often the case in multi-author books.

Finally, and most importantly, we are indebted to all the authors for all their efforts in the preparation of their contributions, which we hope the readers will appreciate.

The editors would like to dedicate this book to the memory of our colleague and friend Christian G. Claessens, who recently passed away.

TOMÁS TORRES GIOVANNI BOTTARI

Universidad Autónoma de Madrid, SpainApril 2013

CONTRIBUTORS

Takeshi Akasaka, Life Science Center of Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Ibaraki 305-8577, Japan; and College of Materials Science and Engineering, Huazhong University of Science and Technology, Wuhan, Hubei 430074, China

David B. Amabilino, Institut de Ciència de Materials de Barcelona, Consejo Superior de Investigaciones Científicas, Campus Universitari de Bellaterra, 08193 Cerdanyola del Vallès, Catalonia, Spain

Ildiko Badea, College of Pharmacy and Nutrition, University of Saskatchewan, Saskatoon, Saskatchewan, S7N 5C9, Canada

Juergen Bartelmeß, Department of Chemistry and Pharmacy, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, 91058 Erlangen, Germany

Mario Barteri, Department of Chemistry, Universitá “La Sapienza”, 00195, Rome, Italy

Fabio Biscarini, Università degli Studi di Modena e Reggio Emilia, Dipartimento di Scienze della Vita, via Campi 183, I-41125, Modena Italy and Consiglio Nazionale delle Ricerche (CNR), Istituto per lo Studio dei Materiali Nanostrutturati (ISMN), 40129 Bologna, Italy

Giovanni Bottari, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain; and IMDEA Nanociencia, C/Faraday 9, Ciudad Universitaria de Canto Blanco, E28049 Madrid, Spain

Matteo Calvaresi, Dipartimento di Chimica “G. Ciamician”, Università di Bologna, 40126 Bologna, Italy

David Canevet, Laboratoire MOLTECH-Anjou, 49045 ANGERS Cedex 01, France

Stefano Casalini, Consiglio Nazionale delle Ricerche (CNR), Istituto per lo Studio dei Materiali Nanostrutturati (ISMN), 40129 Bologna, Italy

Massimiliano Cavallini, Consiglio Nazionale delle Ricerche (CNR), Istituto per lo Studio dei Materiali Nanostrutturati (ISMN), 40129 Bologna, Italy

Jørn B. Christensen, Department of Chemistry, University of Copenhagen, DK-2100 Copenhagen, Denmark

Tobias Cramer, Consiglio Nazionale delle Ricerche (CNR), Istituto per lo Studio dei Materiali Nanostrutturati (ISMN), 40129 Bologna, Italy

Leroy Cronin, School of Chemistry, University of Glasgow, Glasgow, G12 8QQ, United Kingdom

Tatiana Da Ros, Center of Excellence for Nanostructured Materials (CENMAT), INSTM—Unit of Trieste, Dipartimento di Scienze Chimiche e Farmaceutiche, Università degli Studi di Trieste, 34127 Trieste, Italy

Luisa De Cola, Université de Strasbourg, Institut de Science et d'Ingénierie Supramoléculaires (ISIS), 67083 Strasbourg, France

André Devaux, Department of Chemistry, University of Fribourg, CH- 1700 Fribourg, Switzerland

McDonald Donkuru, College of Pharmacy and Nutrition, University of Saskatchewan, Saskatoon, Saskatchewan, S7N 5C9, Canada

Francis D'Souza, Department of Chemistry, University of North Texas, Denton, TX 76203-5017, United States

Lourdes E. Echegoyen, Department of Chemistry, University of Texas at El Paso, El Paso, TX 79968, United States

Luis Echegoyen, Department of Chemistry, University of Texas at El Paso, El Paso, TX 79968, United States

Mahmoud Elsabahy, School of Pharmacy, University of Waterloo, Waterloo, Ontario, N2L 3G1, Canada. Current affiliations: Department of Pharmaceutics, Faculty of Pharmacy, Assiut University, Assiut, Egypt; and Laboratory for Synthetic-Biologic Interactions, Department of Chemistry, Texas A&M University, College Station Texas, 77842, United States

Chiara Fabbro, Center of Excellence for Nanostructured Materials (CENMAT), INSTM—Unit of Trieste, Dipartimento di Scienze Chimiche e Farmaceutiche, Università degli Studi di Trieste, 34127 Trieste, Italy. Current affiliation: Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca' Foscari di Venezia, 30123 Venezia, Italy

Lai Feng, Department of Physical Science and Technology, School of Energy, Soochow University, Suzhou, Jiangsu 215006, China; and Life Science Center of Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Ibaraki 305-8577, Japan

Marianna Foldvari, Canada Research Chair in Bionanotechnology and Nanomedicine, Waterloo Institute of Nanotechnology, School of Pharmacy, University of Waterloo, Waterloo, Ontario, N2L 3G1, Canada

Shunichi Fukuzumi, Department of Material and Life Science, Graduate School of Engineering, Osaka University and ALCA (JST), 2-1 Yamada-oka, Suita, Osaka 565-0871, Japan; and Department of Bioinspired Science, Ewha Womans University, Seoul 120-750, Korea

José M. Gallego, Instituto de Ciencia de Materiales de Madrid, Consejo Superior de Investigaciones Científicas, 28049 Madrid, Spain

Michael Grätzel, Laboratory of Photonics and Interfaces (LPI), Ecole Polytechnique Federale de Lausanne, CH-1015 Lausanne, Switzerland

Dirk M. Guldi, Department of Chemistry and Pharmacy, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, 91058 Erlangen, Germany

Jurriaan Huskens, Department of Science and Technology, Molecular Nanofabrication Group, MESA+ Institute for Nanotechnology, University of Twente, 7500 AE Enschede, Netherlands

Søren Hvilsted, Danish Polymer Centre, Department of Chemical and Biochemical Engineering, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark

Osamu Ito, CarbonPhotoScience Lab., Kita-Nakayama 2-1-6, Izumi-ku, Sendai, 981-3215, Japan

Irakli Javakhishvili, Danish Polymer Centre, Department of Chemical and Biochemical Engineering, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark

Pascal Jonkheijm, Department of Science and Technology, Molecular Nanofabrication Group, MESA+ Institute for Nanotechnology, University of Twente, 7500 AE Enschede, Netherlands

Jaejung Ko, Department of New Material Chemistry, Korea University, Jochiwon, Chungnam 339-700, Korea.

Takahiko Kojima, Department of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennoudai, Tsukuba, Ibaraki 305-8571, Japan

Koichi Komatsu, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan

Anna Laromaine, Institut de Ciència dels Materials de Barcelona, ICMAB-CSIC, Campus UAB, 08193 Bellaterra, Spain

Francesca Leonardi, Consiglio Nazionale delle Ricerche (CNR), Istituto per lo Studio dei Materiali Nanostrutturati (ISMN), 40129 Bologna, Italy

Fang-Fang Li, Department of Chemistry, University of Texas at El Paso, El Paso, TX 79968, United States

Xing Lu, State Key Laboratory of Material Processing and Die & Mould Technology, College of Materials Science and Engineering, Huazhong University of Science and Technology, Wuhan, Hubei 430074, China; and Life Science Center of Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Ibaraki 305-8577, Japan

Henning Lülf, Université de Strasbourg, Institut de Science et d'Ingénierie Supramoléculaires (ISIS), 67083 Strasbourg, France

Andrew Macdonell, School of Chemistry, University of Glasgow, Glasgow, G12 8QQ, United Kingdom

Charles R. Mace, Diagnostics For All, 840 Memorial Drive, Cambridge, MA 02139, United States

Nazario Martín, Facultad de Ciencias Químicas, Departamento de Química Orgánica, Universidad Complutense de Madrid, 28040 Madrid, Spain; and IMDEA Nanociencia, Ciudad Universitaria de Canto Blanco, E28049 Madrid, Spain

Craig J. Medforth, REQUIMTE/Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto, Portugal

Rodolfo Miranda, Departamento de Física de la Materia Condensada, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain

Pedro Molina, Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, Campus de Espinardo, E-30100 Murcia, Spain

Michihisa Murata, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan

Yasujiro Murata, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan

Shigeru Nagase, Fukui Institute for Fundamental Chemistry, Kyoto University, Sakyo-ku, Kyoto 606-8103, Japan

Mohammad Khaja Nazeeruddin, Laboratory of Photonics and Interfaces (LPI), Ecole Polytechnique Federale de Lausanne, CH-1015 Lausanne, Switzerland; and University, Jochiwon, Chungnam 339-700, Korea

Roberto Otero, Departamento de Física de la Materia Condensada, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain

Emilio M. Pérez, IMDEA Nanociencia, Ciudad Universitaria de Canto Blanco, E28049 Madrid, Spain

Eko Adi Prasetyanto, Université de Strasbourg, Institut de Science et d'Ingénierie Supramoléculaires (ISIS), 67083 Strasbourg, France

Maurizio Prato, Center of Excellence for Nanostructured Materials (CENMAT), INSTM—Unit of Trieste, Dipartimento di Scienze Chimiche e Farmaceutiche, Università degli Studi di Trieste, 34127 Trieste, Italy

Imma Ratera, Department of Molecular Nanoscience and Organic Materials, Institut de Ciència de Materials de Barcelona (ICMAB-CSIC)/CIBER-BBN, Campus de la UAB, 08193 Bellaterra, Spain

David González-Rodríguez, Nanostructured Molecular Systems and Materials Laboratory, Departamento de Química Orgánica, Universidad Autónoma de Madrid, 28049 Madrid, Spain

Atula S. D. Sandanayaka, School of Materials Science, Japan Advanced Institute of Science and Technology (JAIST), Nomi, Ishikawa, 923-1292, Japan

Niyazi Serdar Sariciftci, Linz Institute for Organic Solar Cells (LIOS), Physical Chemistry, Johannes Kepler University of Linz, A-4040 Linz, Austria

Satoru Sato, Life Science Center of Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Ibaraki 305-8577, Japan

Francesca A. Scaramuzzo, Department of Science and Technology, Molecular Nanofabrication Group, MESA+ Institute for Nanotechnology, University of Twente, 7500 AE Enschede, Netherlands

Albertus P. H. J. Schenning, Laboratory for Functional Organic Materials and Devices, Eindhoven University of Technology, 5600 MB Eindhoven, The Netherlands

John A. Shelnutt, Department of Chemistry, University of Georgia, Athens, GA 30602, United States

Yuta Takano, Life Science Center of Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Ibaraki 305-8577, Japan

Alberto Tárraga, Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, Campus de Espinardo, E-30100 Murcia, Spain

Donald A. Tomalia, NanoSynthons LLC, The National Dendrimer and Nanotechnology Center, 1200 N. Fancher Avenue, Mount Pleasant, MI, 48858, United States

Tomás Torres, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain; and IMDEA Nanociencia, C/Faraday 9, Ciudad Universitaria de Canto Blanco, E28049 Madrid, Spain

Pavel A. Troshin, Institute for Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Moscow Region, 142432, Russia

Maxence Urbani, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain

Jaume Veciana, Department of Molecular Nanoscience and Organic Materials, Institut de Ciència de Materials de Barcelona (ICMAB-CSIC)/CIBER-BBN, Campus de la UAB, 08193 Bellaterra, Spain

Marisela Vélez, Instituto de Catálisis y Petroleoquímica, Consejo Superior de Investigaciones Científicas, Campus de Cantoblanco, 28049 Madrid, Spain

Ronald Verrall, Department of Chemistry, University of Saskatchewan, Saskatoon, Saskatchewan, S7N 5C9, Canada

Adrián Villalta-Cerdas, Department of Chemistry, University of Texas at El Paso, El Paso, TX 79968, United States

Michio Yamada, Department of Chemistry, Tokyo Gakugei University, Koganei, Tokyo 184-8501, Japan

Francesco Zerbetto, Dipartimento di Chimica “G. Ciamician”, Università di Bologna, 40126 Bologna, Italy