Functional Organic Liquids

The first book to comprehensively cover the burgeoning new class of soft materials known as functional organic liquids

Functional organic liquids, a new concept in soft matter materials science, exhibit favorable properties compared to amorphous polymers and ionic liquids. They are composed of a functional core unit and a side chain, which induces fluidity even at room temperature. Due to their fluidity, functional organic liquids can adopt any shape and geometry and fulfill their function in stretchable and bendable devices for applications in photovoltaics, organic electronics, biomedicine, and biochemistry.

Presented in five parts, this book starts with an overview of the design methods and properties of functional organic liquids. The next three parts focus on the applications of this exciting new class of soft materials in the fields of energy conversion, nanotechnology, and biomaterials. They study the liquids for energy conversion, those containing inorganic nanoclusters, and solvent-free soft biomaterials. Functional Organic Liquids concludes with a comparison in terms of properties and application potential between functional organic liquids and more conventional soft matter such as ionic liquids and liquid metals.

-Examines the current state of science and technology for functional organic liquids
-Focuses on potential and already realized applications such as functional organic liquids for energy conversion
-Stimulates researchers to move forward on future development and applications

Functional Organic Liquids is an excellent book for materials scientists, polymer chemists, organic chemists, physical chemists, surface chemists, and surface physicists.

Autorentext

Takashi Nakanishi, PhD, is a group leader at the International Center for Materials Nanoarchitectonics (WPI-MANA) at the National Institute for Materials Science (NIMS), Japan. He obtained his PhD from Nagasaki University, Japan, and subsequently was postdoctoral researcher at Houston University, USA, and Oxford University, UK. Takashi Nakanishi was group leader at the Max Planck Institute of Colloids and Interfaces and researcher at the Japanese Science and Technology Agency before taking up his current position.

Inhalt
Preface xi

1 Room-Temperature Liquid Dyes **1
**Bhawani Narayan and Takashi Nakanishi

1.1 Introduction 1

1.2 Design Strategy: Alkyl Chain Engineering 2

1.3 Alkylated -Molecular Liquids 3

1.3.1 Carbazoles 3

1.3.2 Azobenzenes 5

1.3.3 Naphthalenes 6

1.3.4 Anthracenes 6

1.3.5 Pyrenes 8

1.3.6 -Conjugated Oligomers 10

1.3.6.1 Oligo-(p-phenylenevinylene)s (OPVs) 10

1.3.6.2 Oligo-(p-phenyleneethylene)s (OPEs) 11

1.3.6.3 Benzothiadiazoles (BTDs) 12

1.3.7 Porphyrins 12

1.3.8 Fullerenes 12

1.4 Alkylsilane-Chain-Appended -Molecular Liquids 13

1.4.1 Triarylamines 14

1.4.2 Phthalocyanines 15

1.4.3 Oligofluorenes 15

1.5 Analytical Tools for Functional Molecular Liquids 16

1.5.1 Analytical Tools for Bulk Physical Properties 16

1.5.1.1 Structural Analysis 16

1.5.1.2 Microscopy Techniques 16

1.5.1.3 Rheology 16

1.5.1.4 Calorimetric Techniques 17

1.5.2 Analytical Tools for Spectroscopic Properties 17

1.5.2.1 UVvis Analysis 17

1.5.2.2 Fluorescence Measurements 17

1.5.2.3 Fluorescence Lifetime Analysis 17

1.5.2.4 FTIR Measurements 17

1.6 Conclusion 18

References 18

2 Low-Melting Porphyrins and Their Photophysical Properties **21
**Agnieszka Nowak-Król and Daniel T. Gryko

2.1 Introduction 21

2.2 Liquid Porphyrins 22

2.3 Low-Melting trans-A2B2-Arylethynyl Porphyrins 28

2.4 Liquid Crystalline trans-A2B2-Arylethynyl Porphyrins 31

2.5 Bis-porphyrins 31

2.6 Low-Melting Corroles 34

2.7 Summary and Outlook 34

References 35

3 Porous Liquids **39
**Stuart L. James and Ben Hutchings

3.1 Introduction 39

3.2 Porosity in Solids 40

3.3 Porosity in Liquids 41

3.4 Porous Liquids Reported in the Literature 43

3.4.1 Type 1 43

3.4.2 Type 2 46

3.4.3 Type 3 48

3.4.4 Other Types of Porous Liquids and Theoretical Studies 48

3.5 Opportunities for Applications and Current Challenges 49

3.6 Concluding Remarks 50

References 50

4 Cyclic Host Liquids for the Formation of Rotaxanes and Their Applications **53
**Tomoki Ogoshi, Takahiro Kakuta, and Tada-aki Yamagishi

4.1 Introduction 53

4.2 Liquid Pillar[n]arenes at Room Temperature 54

4.2.1 Synthesis and Structure of Pillar[n]arenes 54

4.2.2 Versatile Functionality of Pillar[n]arenes 55

4.2.3 Molecular Design to Produce Liquid-State Macrocyclic Hosts 56

4.2.3.1 Pillar[n]arenes 56

4.2.3.2 Cyclodextrins 58

4.2.3.3 Crown Ethers 60

4.2.3.4 Calix[n]arenes and Cucurbit[n]urils 60

4.3 Complexation of Guest Molecules by Pillar[5]arenes 61

4.3.1 Host Properties of Pillar[5]arenes 61

4.3.2 Complexation of Guest Molecules in Liquid Pillar[5]arenes 62

4.4 High Yield Synthesis of [2]Rotaxane and Polyrotaxane Using Liquid Pillar[5]arenes as Solvents 63

4.5 Conclusion and Remarks 70

References 71

5 Photochemically Reversible Liquefaction/Solidification of Sugar-Alcohol Derivatives **75
**Haruhisa Akiyama

5.1 Introduction 75

5.2 Mechanism of the Phase Transition Between Liquid and Solid State 76

5.3 Effect of Molecular Structure 79

5.3.1 Number of Azobenzene Units 79

5.3.2 Alkyl Chain Length 80

5.3.3 Mixed Arms 82

5.3.4 Structure of Sugar Alcohol 83

5.4 Summary 85

Acknowledgments 85

References 85 <p&gt...