Supramolecular Materials for Opto-Electronics

[BOOK DESCRIPTION]

For years, concepts and models relevant to the fields of molecular electronics and organic electronics have been invented in parallel, slowing down progress in the field. This book illustrates how synthetic chemists, materials scientists, physicists, and device engineers can work together to reach their desired, shared goals, and provides the knowledge and intellectual basis for this venture. Supramolecular Materials for Opto-Electronics covers the basic principles of building supramolecular organic systems that fulfil the requirements of the targeted opto-electronic function; specific material properties based on the fundamental synthesis and assembly processes; and provides an overview of the current uses of supramolecular materials in opto-electronic devices. To conclude, a "what's next" section provides an outlook on the future of the field, outlining the ways overarching work between research disciplines can be utilised. Postgraduate researchers and academics will appreciate the fundamental insight into concepts and practices of supramolecular systems for opto-electronic device integration.

[TABLE OF CONTENTS]

Chapter 1 Self-assembled Supramolecular            1  (52)
Materials in Organic Electronics
          Emilie Moulin
          Eric Busseron
          Nicolas Giuseppone
    1.1 Introduction                               1  (1)
    1.2 Conducting Supramolecular Materials        2  (16)
      1.2.1 Thiophene Derivatives                  2  (4)
      1.2.2 Tetrathiafulvalene Derivatives         6  (1)
      1.2.3 Porphyrins and Pyrroles Derivatives    7  (3)
      1.2.4 Polyaromatic Derivatives               10 (1)
      1.2.5 Perylene Derivatives                   11 (3)
      1.2.6 Triarylamine Derivatives               14 (1)
      1.2.7 Other Aromatic Molecules               15 (3)
    1.3 Organic Field Effect Transistors           18 (8)
      1.3.1 Thiophene Derivatives                  19 (1)
      1.3.2 Tetrathiafulvalene Derivatives         20 (1)
      1.3.3 Phthalocyanine Derivatives             21 (1)
      1.3.4 Perylene Derivatives                   21 (3)
      1.3.5 Other Aromatic Molecules               24 (2)
    1.4 Organic Light-Emitting Devices             26 (6)
      1.4.1 Oligo(phenylenevinylene) Derivatives   26 (1)
      1.4.2 Fluorene Derivatives                   27 (1)
      1.4.3 Polyaromatic Molecules                 27 (2)
      1.4.4 Metallic and Inclusion Complexes       29 (1)
      1.4.5 H-bond and Metallo-supramolecular      30 (2)
      Polymers
    1.5 Organic Photovoltaic Devices               32 (9)
      1.5.1 Thiophene Derivatives                  32 (4)
      1.5.2 Porphyrin and Phthalocyanine           36 (1)
      Derivatives
      1.5.3 Diketopyrrolopyrrole Derivatives       37 (1)
      1.5.4 Hexabenzocoronene Derivatives          38 (1)
      1.5.5 Rylene Derivatives                     39 (1)
      1.5.6 Triarylamines Molecules                40 (1)
      1.5.7 Other Aromatic Molecules               40 (1)
    1.6 Conclusion                                 41 (1)
    Acknowledgements                               42 (1)
    References                                     42 (11)
Chapter 2 Multicomponent Assembly Strategies       53 (45)
for Supramolecular Systems
          Dimas G. de Oteyza
    2.1 Introduction                               53 (2)
    2.2 Taming the Driving Forces behind           55 (25)
    Multicomponent Self-Assembly
      2.2.1 Molecule-Substrate Interactions        57 (6)
      2.2.2 Intermolecular Interactions            63 (17)
    2.3 Electronic Considerations in               80 (8)
    Multicomponent Molecular Assemblies
      2.3.1 Standard Interfacial Models            80 (4)
      2.3.2 Supramolecular                         84 (4)
      Environment-Dependent Electronic
      Properties
    2.4 Concluding Remarks                         88 (1)
    References                                     89 (9)
Chapter 3 Low-Dimensional Supramolecular           98 (21)
Assemblies on Surfaces
          Tianchao Niu
          Jia Lin Zhang
          Wei Chen
    3.1 Introduction                               98 (1)
    3.2 1D Molecular Chains                        99 (7)
      3.2.1 Substrate Template Directed            100(1)
      Self-Assembly of 1D Molecular Chains
      3.2.2 1D Molecular Chains Assembled          101(2)
      through Hydrogen Bonding
      3.2.3 Metal-Organic Coordination Bonds       103(1)
      Assisted Assembly of 1D Molecular Chains
      3.2.4 On-Surface Synthesis towards           104(2)
      Covalently Bonded 1D Molecular Chains
    3.3 2D Molecular Networks                      106(9)
      3.3.1 Single-Component Supramolecular        107(2)
      Structures on Surfaces
      3.3.2 Binary Molecular Networks              109(3)
      3.3.3 On-Surface Covalent-Bonded             112(3)
      Molecular Networks
    3.4 Conclusion                                 115(1)
    Acknowledgement                                116(1)
    References                                     116(3)
Chapter 4 Self-Assembled Mono- and Multilayers     119(54)
for Functional Opto-Electronic Devices
          Antonio Facchetti
          Rocio Ponce Ortiz
          Tobin J. Marks
    4.1 Introduction                               119(1)
    4.2 Concepts of Molecular Self-Assembly for    120(5)
    Mono- and Multilayer Fabrication and
    Function
    4.3 Applications of SAM and SAMT to Organic    125(34)
    Opto-Electronic Devices
      4.3.1 Organic Field-Effect Transistors       128(16)
      4.3.2 Bulk-Heterojunction Solar Cells        144(8)
      4.3.3 Organic Light-Emitting Diodes          152(2)
      4.3.4 Electro-Optic Devices                  154(5)
    4.4 Conclusions 158 Acknowledgments            159(1)
    References                                     159(14)
Chapter 5 Amphiphilic Design for Supramolecular    173(30)
Materials with Opto-Electronic Functions
          Subi J. George
          Ankit Jain
          K. Venkata Rao
    5.1 Introduction                               173(3)
    5.2 Electronic Functionality                   176(15)
      5.2.1 p-Type Semiconducting Amphiphiles      176(5)
      5.2.2 n-Type Semiconducting Amphiphiles      181(2)
      5.2.3 Miscellaneous π-Conjugated          183(3)
      Amphiphiles
      5.2.4 Multi-chromophoric p-n Amphiphiles     186(4)
      5.2.5 Supramolecular Amphiphiles             190(1)
    5.3 Optical Functionality                      191(7)
    5.4 Conclusion                                 198(1)
    References                                     198(5)
Chapter 6 Chiral Supramolecular Structures as      203(23)
Spin Filters
          Ron Naaman
          David H. Waldeck
    6.1 Introduction                               203(2)
    6.2 Theory                                     205(3)
      6.2.1 Spin-Orbit Coupling Magnitude          207(1)
      6.2.2 Resonances                             207(1)
    6.3 Experimental Results                       208(10)
      6.3.1 Spin-Dependent Photoelectron           208(3)
      Transmission
      6.3.2 Spin-Dependent Conductivity            211(7)
    6.4 Applications and Implications              218(4)
      6.4.1 Memory Device                          218(4)
    6.5 Conclusions                                222(1)
    Acknowledgements                               223(1)
    References                                     223(3)
Chapter 7 Solution Processed Multilayer Organic    226(47)
Light Emitting Diodes
          Manuel Auer
          Leonid Pevzner
          Stefan Sax
          Emil J.W. List-Kratochvil
    7.1 Introduction                               226(3)
    7.2 Multilayer Structures from the same        229(6)
    Solvent by Diverse Fabrication Strategies
      7.2.1 Blade Coating                          230(1)
      7.2.2 Liquid Buffer Layer                    231(1)
      7.2.3 Electrospray Deposition                232(1)
      7.2.4 Transfer Printing                      233(1)
      7.2.5 Lamination                             234(1)
    7.3 Multilayer Structures from the same        235(15)
    Solvent by Chemical Reaction
      7.3.1 Cross-Linking by the Addition of       236(10)
      Reactive Groups
      7.3.2 Thermal Stabilization                  246(1)
      7.3.3 The Precursor Route                    247(1)
      7.3.4 Universal Cross-Linking                248(2)
    7.4 Multilayer Structures from Orthogonal      250(15)
    Solvents
      7.4.1 Polar Solvents                         252(5)
      7.4.2 Fluorinated Solvents                   257(2)
      7.4.3 Hybrid Approaches                      259(6)
    7.5 Conclusion and Outlook                     265(1)
    Acknowledgements                               266(1)
    References                                     266(7)
Chapter 8 Concepts and Modeling for Charge         273(36)
Transport in Organic Electronic Materials
          K. Sebastian Radke
          F. Ortmann
          G. Cuniberti
    8.1 Introduction                               273(2)
    8.2 Kubo Formalism                             275(2)
    8.3 Ab Initio Material Parameters and          277(5)
    Disorder Models
      8.3.1 Hamiltonian for Coupled Electrons      277(2)
      and Phonons
      8.3.2 Ab Initio Material Parameters          279(3)
      8.3.3 Disorder Models                        282(1)
    8.4 Polaron Transport Approaches               282(7)
      8.4.1 Three-Dimensional Anisotropic          283(3)
      Mobility
      8.4.2 Limiting Cases                         286(3)
    8.5 Quantum Dynamic Charge Propagation         289(15)
    Techniques
      8.5.1 Introduction                           289(2)
      8.5.2 Polaron Theory Based Charge            291(1)
      Propagation
      8.5.3 Mixed Quantum-Classical Propagation    292(12)
    8.6 R駸um?                                     304(1)
    Acknowledgements                               305(1)
    References                                     305(4)
Chapter 9 Simulations of Morphology and Charge     309(54)
Transport in Supramolecular Organic Materials
          Denis Andrienko
    9.1 Introduction                               309(5)
    9.2 Morphology Simulations                     314(6)
      9.2.1 first-Principles Calculations          315(1)
      9.2.2 Atomistic Models                       316(2)
      9.2.3 Coarse-Grained Models                  318(2)
    9.3 Charge Transport                           320(17)
      9.3.1 Diabatic States                        321(3)
      9.3.2 Charge Transfer Rates                  324(1)
      9.3.3 Electronic Coupling Elements           325(3)
      9.3.4 Reorganization Energies                328(1)
      9.3.5 Driving Forces                         328(7)
      9.3.6 Charge Mobility                        335(2)
    9.4 Finite-Size Effects                        337(1)
    9.5 Stochastic Models                          338(1)
    9.6 Interfaces and Long-Range Interactions     339(2)
    9.7 Excited States                             341(1)
    9.8 Software                                   342(2)
    9.9 Outlook                                    344(1)
    Acknowledgements                               344(1)
    References                                     345(18)
Subject Index                                      363