Molecular photoswitches : chemistry, properties, and applications / edited by Zbigniew L. Pianowski

Format:

Book

Contributor:

Pianowski, Zbigniew L., editor.

Wiley InterScience (Online service)

Language:

English

Subjects (All):

Molecular machinery.

Optical detectors.

Photochromism.

Physical Description:

1 online resource (2 volumes (1148 pages))

Place of Publication:

Weinheim, Germany : Wiley-VCH, [2022]

System Details:

text file

Contents:

Cover

Title Page

Copyright

Contents

Foreword

Preface

Part I Interplay of Light and Matter

Chapter 1 Physicochemical Aspects of Photoswitching

1.1 Introduction

1.2 Essentials of Photophysics

1.2.1 Quantum Yield

1.2.2 Photostationary State

1.2.3 Photoactivation

1.3 Spectroscopy of Photoswitching

1.4 Two Case Examples

1.4.1 Diarylethenes

1.4.2 Azobenzene and Its Derivatives

References

Chapter 2 Computational Methods and Photochromism

2.1 Introduction

2.2 Basics of Computational Photochemistry

2.2.1 Electronic Structure Methods

2.2.2 Photochemical Pathway and Conical Intersections

2.3 Applications: Photoswitching Mechanisms of Photochromic Compounds

2.3.1 Dihydroazulene Photochromism

2.3.2 Dihydropyrene Photochromism

2.4 Conclusions and Perspectives

Part II Chemical Classes of Molecular Photoswitches

Chapter 3 Azobenzenes: The Quest for Visible Light Triggering

3.1 Introduction

3.1.1 Azobenzene and Its Physical Characteristics

3.2 Synthesis of Azobenzenes

3.2.1 Synthesis of Symmetrical Azobenzenes by Oxidation of Anilines

3.2.2 Azo Coupling

3.2.3 Mills Reaction

3.2.4 Modern Methods

3.3 Visible Light-Activated Azobenzenes as Photoswitches

3.3.1 The Effect of Electron-Donating Groups on Direct Photoexcitation

3.3.2 The Effect of Electron-Withdrawing Groups on Direct Photoexcitation

3.3.3 Further Modification Leading to Visible Light Photoswitches

3.3.4 Complex Molecular and Supramolecular Systems Containing Azobenzenes

3.4 Applications of Azobenzenes in Biological Systems

3.5 Conclusion

Chapter 4 Diazocines: Photoswitches with Excellent Photophysical Properties and Inverted Stabilities

4.1 Photophysical Properties and Conformations of Parent Diazocine

4.2 Synthesis of Diazocines.

11.2.4 Third-Generation Rotary Molecular Motors

11.3 Dynamics and Kinetics of Molecular Motors

11.3.1 Thermal Isomerization

11.3.2 Tuning the Speed of Rotation

11.3.3 Photoisomerization

11.3.4 Tuning the Absorption Wavelength

11.3.5 Photochemical Motors

11.3.6 Novel Motor Core Designs

11.4 Applications

11.4.1 Transfer of Chirality

11.4.2 Transfer of Motion

11.4.2.1 Coupled Rotary Systems

11.4.2.2 Translation of Motion

11.4.2.3 Control Over Motion

11.4.3 Biological Applications

11.4.4 Other Applications

11.5 Perspective and Outlook

Chapter 12 Stilbenes Revisited: Understanding the Mechanism of Mechanochemical Coupling

12.1 Introduction

12.2 Stiff Stilbene as a Molecular Force Probe

12.2.1 Introduction to Polymer Mechanochemistry

12.2.2 The Importance of Model Studies in Polymer Mechanochemistry

12.2.3 Stiff Stilbene Is an Effective Molecular Force Probe

12.2.4 How Intrinsic Mechanochemical Reactivity Is Measured with Stiff Stilbene

12.2.5 How Stiff Stilbene Advanced Our Understanding of Mechanochemistry

12.2.5.1 The Restoring Force of a Stretched Monomer Predicts Its Reactivity Independent of How the Force Is Generated

12.2.5.2 Experimental Validation of a Simple Model of Mechanochemical Kinetics Over Complex Energy Landscapes

12.2.5.3 The Diversity of Force-Reactivity Relationships

12.3 Stilbenes in Fundamental Studies of Energy Transduction by Molecular Motors

12.3.1 Introduction to Molecular Machines

12.3.2 Minimalist Design of a Molecular Rotor Realized Using Stilbenes

12.4 Summary

Chapter 13 Indigoid Photoswitches

13.1 Indigo

13.2 Thioindigo

13.3 Hemiindigo

13.4 Hemithioindigo

13.5 Iminothioindoxyls

13.6 Oxindoles and Isoindolinones

Chapter 14 Donor-Acceptor Stenhouse Adducts.

14.1 Introduction

14.2 DASA Synthesis

14.2.1 Molecular Photoswitch

14.2.2 Photoswitches in Macromolecules

14.3 Photoswitching Properties

14.3.1 Mechanism

14.3.2 The Absorption Properties

14.3.3 Dark Equilibria

14.3.4 Cyclization Efficiency Under Illumination

14.3.5 Electronic Effects

14.3.6 Steric Effects

14.3.7 Solvent Effects

14.3.8 Concentration Effects

14.3.9 Cyclization Under Exclusion of Light

14.3.10 Role of Water and Substituents on Cyclization and Ring Opening

14.4 Illustrative Applications

14.4.1 Polarity Change

14.4.2 Wavelength Selectivity

14.4.3 Sensing

14.4.4 Photothermal

14.5 Conclusion

Chapter 15 Imines as Threefold Functional Devices: Motional, Photochemical, Constitutional

15.1 Introduction

15.2 Imine Photoswitches

15.2.1 Electronic Spectra and Photochemical E/Z-Isomerization of Imines

15.2.2 Thermal E/Z-Isomerization of Imines

15.2.3 Imines as Photoswitches

15.2.4 Imines as Light-Driven Molecular Motors

15.3 Acylhydrazone and Hydrazone Photoswitches

15.3.1 The Triple Dynamics of Imine-Based Photoswitches

15.3.2 The Consequences of Pyridyl-Hydrazones Shape Switching

15.3.2.1 Photo-Responsive Receptor

15.3.2.2 Switchable Catalysis

15.3.2.3 Control of Supramolecular Polymerization

15.3.2.4 The Dynamics of Molecular Movements

15.3.2.5 Adaptation

15.3.3 Constitutional Dynamic Networks

15.3.3.1 Photoswitching of Constitutional Dynamic Networks

15.3.3.2 Photoswitching in Dynamic Covalent Chemistry: The Photodynamic Covalent Bond

15.4 Conclusion

Chapter 16 Norbornadiene/Quadricyclane (NBD/QC) and Conversion of Solar Energy

16.1 Introduction

16.2 Synthesis

16.2.1 Norbornadiene (NBD)

16.2.2 Quadricyclane (QC).

16.3 Molecular Engineering of the Norbornadiene/Quadricyclane Photoswitch Toward MOST Application.

Notes:

Includes bibliographical references

Electronic reproduction. Hoboken, N.J. Available via World Wide Web.

Description based on online resource; title from PDF title page (Wiley Online LIbrary, viewed June 14, 2022)

Other Format:

Print version: Molecular photoswitches.

ISBN:

9783527827602

3527827609

9783527827619

3527827617

9783527827626

3527827625

Publisher Number:

99993745629

Access Restriction:

Restricted for use by site license.