Master the unique architecture of azulene and unlock its transformative potential across organic semiconductors, molecular switches, and advanced materials with this authoritative, future-focused guide to the next frontier of organic electronics.
In the era of digitalization, organic electronics are expected to be pivotal in shaping the future. Azulene, a unique bicyclic hydrocarbon with remarkable structural and electronic properties, has found significant applications in organic electronics, optoelectronics, and materials science. This book provides an in-depth exploration of azulene chemistry, from its discovery and isolation to its cutting-edge applications in fields like organic semiconductors, molecular switches, and sensors. It offers detailed insights into the synthesis methods of azulene and its derivatives, focusing on both classical and modern approaches, and highlights the functionalization of azulene systems for use in advanced materials like nanographenes and porous polymers. It also covers the application of azulene derivatives in fields such as organic photovoltaics, field-effect transistors, and photochromic compounds for molecular switching. With a focus on the multidisciplinary nature of azulene chemistry, the text explores its potential in biological applications, including antimicrobial, anti-inflammatory, and antiviral properties, as well as its role in catalysis and energy storage. Designed as a comprehensive guide, this book serves as an invaluable reference for material chemists, organic chemists, physicists, and students engaged in research on azulene-based systems. By compiling the most significant findings in azulene chemistry, it offers a solid foundation for future research and development, addressing challenges in organic synthesis, optoelectronics, and emerging technologies, with an eye toward the future role of artificial intelligence in advancing the field.
The reader will find the volume:
- Serves as an authoritatively comprehensive guide to azulene chemistry;
- Discusses the synthesis of azulene and its derivatives, as well as the applications of azulene and azulene-based materials across a wide array of fields;
- Explores the emerging field of the synthetic chemistry of azulenes and calixazulenes.
Audience
Researchers in academia, material chemists and physicists, industry and government laboratories as well as advanced undergraduate and graduate students working in organic synthesis, organic electronics, organic semiconducting systems.
Table of Contents:
Preface xiii
Part 1: Fundamental Aspects of Azulene Chemistry 1
1 Discovery and Structural Insights into Azulene 3
Sahid S.K., Nasseb Singh, Manda Sathish, Alamgir Ahmad Dar and Neha Rani Kumar
1.1 Introduction 4
1.2 Discovery and Synthesis of Azulene 5
1.3 Structural Insights 8
1.4 Applications of Azulene and Its Derivatives 13
1.5 Conclusion 15
2 Azulene-Containing Natural Products 19
Abhilash Sharma, Hemanta Hazarika and Dhrubajit Borah
2.1 Introduction 19
2.2 Occurrence and Isolation of Guaiazulene and Chamazulene 21
2.3 Synthesis of Guaiazulene 28
2.4 Synthesis of Chamazulene 38
2.5 Applications 44
2.6 Conclusion 45
3 Synthesis of Azulene and Its Functionalized Derivatives 53
G.B. Dharma Rao, Aditi Tiwari, A. Udayasri and Anjaneyulu Bendi
3.1 Introduction 54
3.2 Traditional Process for the Synthesis of Azulene 55
3.3 Synthesis of Azulene Derivatives 57
3.4 Conclusion 76
4 Azaazulenes: Synthesis, Reactivity, and Applications 81
R. Balavardhana Rao Adapa
4.1 Introduction 82
4.2 Types of Azaazulene Isomers 82
4.3 Synthesis of Azaazulenes 85
4.4 Reactions of Azaazulene 102
4.5 Applications 109
Part 2: Azulene in Functional and Bioactive Materials 117
5 Azulene-Based System in Optoelectronics 119
Parth, Shivani and Amrit Kaur
5.1 Introduction 120
5.2 Applications in Nonlinear Optics 121
5.3 Applications in Molecular Devices 125
5.4 Applications in Organic Field Effect Transistors 128
5.5 Application in Organic Photovoltaics 135
5.6 Miscellaneous Studies 138
5.7 Conclusions 141
6 Azulene-Based Systems as Molecular Switches 151
Sariful Molla and Sheelbhadra Chatterjee
6.1 Introduction 151
6.2 Azulene-Fused Molecular Switches 153
6.3 Azulene-Functionalized Azobenzene Switches 166
6.4 Conclusion and Future Prospects 173
7 Azulene-Based π-Functional Materials and Their Application as Sensors 179
Bagmita Bhattacharyya and Kangkana Deka
7.1 Introduction 179
7.2 Application of Azulene and Its Derivatives for Sensing of Heavy Metals 181
7.3 Azulene-Based Sensors for Detection of Anions 186
7.4 Bioimaging 192
7.5 Conclusion 195
8 Exploring the Synthesis and Characteristics of Nanographenes and PAHs with Azulene Embedment 199
Dileep Kumar Singh and Bijoy P. Mathew
8.1 Introduction 200
8.2 Azulene-Based Polycyclic Aromatic Hydrocarbon 202
8.3 Azulene-Embedded Nanographenes 226
8.4 Conclusion 237
9 Azulene-Based Systems of Biological Significance 245
Sunita Singh, Pragati Kushwaha, Pankaj Kumar Chaurasia, Shashi Lata Bharati, Ayman Younes Fathy Allam, Dhananjay Kumar Singh and Naveen Kumar
9.1 Azulenes, Their Sources, and Therapeutic Innovations 246
9.2 Azulene and Its Derivatives with Biological Significance 248
9.3 Challenges and Future Prospects 265
Part 3: Azulene in Porous and Coordination Chemistry 275
10 Azulene-Based Porous Materials: Synthesis and Applications 277
Debajit Bora, Bikash Chandra Mushahary, Chayanika Goswami and Sanjeev Pran Mahanta
10.1 Porous Materials 278
10.2 Azulene and Its Electronic Properties 279
10.3 Functionalization of the Azulene Derivatives 281
10.4 Synthetic Methods to Prepare Porous Materials 282
10.5 Different Types of Azulene-Based Porous Materials and Their Applications 284
10.6 Conclusion 302
11 Calixazulenes and Azuliporphyrins 311
Nitika Grover
11.1 Introduction 312
11.2 Azuliporphyrin 313
11.3 Calixazulenes 322
11.4 Conclusion and Outlook 329
12 Functionalization and Utilization of Azulene in Organometallic and Coordination Chemistry 333
Sulendar K. Mahato and Rakesh Kumar Rai
12.1 Introduction 333
12.2 Metallaazulenes 336
12.3 Metal Carbonyl Complexes of Azulene 342
12.4 Coordination Complexes of Azulene 343
12.5 Conclusions 348
Part 4: Theoretical and Future Perspectives 351
13 Theoretical Insights into Azulene Chemistry 353
Manash Protim Borpuzari and Abhijit Boruah
13.1 Introduction 353
13.2 Computational Methods to Study Azulene Chemistry 356
13.3 Recent Advances 360
13.4 Conclusion and Outlook 372
14 Future Perspectives of Azulene Chemistry 377
Kalyan Jyoti Kalita and Neha Rani Kumar
14.1 Introduction 377
14.2 Advances in Synthesis 379
14.3 Applications and Future Directions 382
14.4 Role of Computational Techniques, Including Artificial Intelligence, in Azulene Chemistry 389
14.5 Conclusion 389
References 390
Index 395
About the Author :
Neha Rani Kumar, PhD is an Assistant Professor in the Department of Chemistry, Dhemaji College, Dhemaji, Assam, India. She has authored several publications on azulenes and porous organic polymers. Her research interests include azulene chemistry, conjugated organic systems, and porous organic polymers and their applications in environmental remediation.
Abhijeet R. Agrawal, PhD is a post-doctoral fellow at the Institute of Chemistry, The Hebrew University of Jerusalem, Israel. He has authored several publications on the design and synthesis of heteroacenes and helicenes. His research interests encompass the synthesis of heteroacenes, design and synthesis of flexible conjugated systems, crystallography, and helicenes.
