Skip to main content
E-Book

£99.99

*VAT

Functional Organic Liquids

Takashi Nakanishi (Editor)

ISBN: 978-3-527-80495-5 March 2019 350 Pages

Description

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.

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 π-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 π-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 π-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 UV–vis 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

6 Functional Organic Supercooled Liquids 87
Kyeongwoon Chung, Da Seul Yang, and Jinsang Kim

6.1 Organic Supercooled Liquids 87

6.2 Stimuli-Responsive Organic Supercooled Liquids 88

6.2.1 Shear-triggered Crystallization 88

6.2.2 Scratch-Induced Crystallization of Trifluoromethylquinoline Derivatives 89

6.2.3 Highly Sensitive Shear-Triggered Crystallization in Thermally Stable Organic Supercooled Liquid of a Diketopyrrolopyrrole Derivative 91

6.3 Highly Emissive Supercooled Liquids 95

6.4 Conclusion 97

References 97

7 Organic Liquids in Energy Systems 101
Pengfei Duan, Nobuhiro Yanai, and Nobuo Kimizuka

7.1 Introduction 101

7.2 Photoresponsive π-Liquids for Molecular Solar Thermal Fuels 102

7.3 Azobenzene-Containing Ionic Liquids and the Phase Crossover Approach 107

7.4 Photon Upconversion and Condensed Molecular Systems 113

7.5 TTA-UC Based on the Amorphous π-Liquid Systems 114

7.6 Photon Upconversion Based on Bicontinuous Ionic Liquid Systems 118

7.7 Conclusion and Outlook 121

References 122

8 Organic Light Emitting Diodes with Liquid Emitters 127
Jean-Charles Ribierre, Jun Mizuno, Reiji Hattori, and Chihaya Adachi

8.1 Introduction 127

8.2 Organic Light-emitting Diodes with a Solvent-Free Liquid Organic Light-emitting Layer 129

8.2.1 Basics of Conventional Solid-state OLEDs 129

8.2.2 First Demonstration of a Fluidic OLED Based on a Liquid Carbazole Host 130

8.2.3 Introduction of an Electrolyte to Improve the Liquid OLED Performance 132

8.2.4 Liquid OLED Material Issues 134

8.3 Microfluidic OLEDs 135

8.3.1 Refreshable Liquid Electroluminescent Devices 135

8.3.2 Fabrication of Microfluidic Organic Light-Emitting Devices 137

8.3.3 Large-Area Flexible Microfluidic OLEDs 137

8.3.4 Multicolor Microfluidic OLEDs 140

8.3.5 Microfluidic White OLEDs 143

8.4 Conclusions 147

References 148

9 Liquids Based on Nanocarbons and Inorganic Nanoparticles 151
Avijit Ghosh and Takashi Nakanishi

9.1 Liquid Nanocarbons 151

9.1.1 Introduction 151

9.1.2 General Synthetic Strategies 151

9.1.3 Liquid Fullerenes 152

9.1.4 Liquid-Like Carbon Nanotubes 154

9.1.5 Fluidic Graphene/Graphene Oxide 156

9.2 Liquids Based on Inorganic Nanoparticles 158

9.2.1 Background 158

9.2.2 Liquid-Like Silica Nanoparticles 159

9.2.3 Functional Colloidal Fluids 160

9.2.4 Fluidic Functional Quantum Dots 161

9.3 Conclusions 162

References 164

10 Solvent-Free Nanofluids and Reactive Nanofluids 169
John Texter

10.1 Introduction 169

10.1.1 Solvent-Free Nanofluids 170

10.1.2 Simulation and Theoretical Modeling 180

10.1.3 Reactive Solvent-Free Nanofluids 183

10.2 Syntheses of Nanofluids 184

10.2.1 Core–Corona–Cap Nanofluid 184

10.2.2 Core-Free Corona–Cap Nanofluid 186

10.2.3 Core–Corona Nanofluid 186

10.3 UV Reactive Nanofluids 187

10.3.1 Model Coatings andThermomechanical Characterization 187

10.3.2 UV Protective Coatings 191

10.4 Polyurethane and Polyurea Coupling of Nanofluids 191

10.4.1 Air-Cured Polyurethane Coupling with Isothiocyanate Nanofluid 192

10.4.2 Air-Cured TDI Coupling with Amino Nanofluid 195

10.4.3 Polyurethane Shape-Memory Materials 196

10.4.4 PDMS-Amino Nanofluids Coupling with HMDI 197

10.4.5 Polyurethane Coupling with Hydroxyl Nanofluid 198

10.5 Epoxy Coupling with Amino Nanofluid 198

10.6 Using Nanofluids to Make Composites Tougher 199

10.6.1 Nanosilica Polyacrylate Nanocomposites 199

10.6.2 MWCNT Polyamide Nanocomposites 200

10.6.3 MnSn(OH)6 Thread Epoxy Nanocomposites 201

10.6.4 Graphene Oxide Epoxy Nanocomposites 201

10.7 Summary and Future Prospects 201

Acknowledgments 203

References 203

11 Solvent-Free Liquids and Liquid Crystals from Biomacromolecules 211
Kai Liu, Chao Ma, and Andreas Herrmann

11.1 Introduction 211

11.2 Solvent-Free Nucleic Acid Liquids 212

11.2.1 Fabrication of Solvent-Free Nucleic Acid Liquids 212

11.2.2 Electrical Applications Based on Solvent-Free Nucleic Acid Liquids 215

11.3 Solvent-Free Protein Liquids 217

11.3.1 Fabrication of Solvent-Free Protein Liquids 217

11.3.2 Electrochemical Applications Based on Solvent-Free Protein Liquids 222

11.3.3 Catalysis of Solvent-Free Enzyme Liquids 224

11.4 Solvent-Free Virus Liquids 226

11.5 Mechanism for the Formation of Solvent-Free Bioliquids 228

11.6 Conclusions and Outlook 229

References 230

12 Ionic Liquids 235
Hiroyuki Ohno

12.1 What Is Ionic Liquid? 235

12.2 Some Physicochemical Properties 236

12.3 Preparation 238

12.4 IL Derivatives 239

12.4.1 Zwitterions 239

12.4.2 Self-Assembled ILs 239

12.4.3 Polymers 241

12.5 IL/Water Functional Mixture 241

12.6 Application 243

12.6.1 Reaction Solvents 243

12.6.2 Electrolyte Solution 243

12.6.3 Biomass Treatment 244

12.6.4 Solvents for Proteins and Biofuel Cell 246

12.7 Summary 247

Acknowledgments 247

References 247

13 Room-Temperature Liquid Metals as Functional Liquids 251
Minyung Song and Michael D. Dickey

13.1 Introduction: Room-temperature Liquid Metals 251

13.1.1 Mercury 251

13.1.2 Gallium-Based Alloys 252

13.1.3 Oxide Skin on Ga Alloys 252

13.2 Removal of Oxide Skin 252

13.3 Patterning Techniques for Liquid Metals 253

13.3.1 Lithography-enabled Processes 254

13.3.2 Injection 255

13.3.3 Subtractive 256

13.3.4 Additive 256

13.4 Controlling Interfacial Tension 257

13.4.1 Surface Activity of the Oxide on Liquid Metal Droplets 258

13.5 Applications of Liquid Metals 261

13.6 Conclusions and Outlook 263

References 263

Index 273