Metal-Free Synthetic Organic Dyes

By Ghodsi Mohammadi Ziarani, Razieh Moradi, Negar Lashgari and Hendrik G. Kruger

Metal- Free Synthetic Organic Dyes is a comprehensive guide to the synthetic, organic dyes that are classified by their chemical structure. As synthetic dyes are playing an increasingly important role in modern life, with applications in both industry and scientific research, this book provides insights on the many research attempts that have been made to explore new photosensitizers in the development of dye sensitized solar cells (DSCs). These novel photosensitizers have incorporated, within their structure, different organic groups, such as coumarins, cyanines, hemicyanines, indolines, triphenylamines, bis(dimethylfluorenyl) aminophenyls, phenothiazines, tetrahydroquinolines, carbazoles, polyenes, fluorenes, and many others.

This comprehensive resource contains color figures and schemes for each dye discussed, and is an invaluable resource for organic, inorganic and analytical chemists working in academia and industry.

• Features a discussion of the synthesis of the new, high-value synthetic dyes and pigments and their applications and performance
• Includes coverage of new photosensitizers and their role in the development of dye sensitized solar cells (DSCs)
• Covers synthesis of the functional dyes that are ideal for applications in the dye and pigment industry, textiles, color science, solar energy materials and solar cells, biomedical sensors, advanced materials, structure and synthesis of materials, and more

• Language: English
• Publisher: Elsevier Science
• Release date: Jul 25, 2018
• ISBN: 9780128156483

Ghodsi Mohammadi Ziarani

Dr. Ziarani received her B.Sc. degree in Chemistry from Teacher Training University, Tehran, Iran, in 1987, her M.Sc. degree in Organic Chemistry from the Teacher Training University, Tehran, Iran, under the supervision of Professor Jafar Asgarin and Professor Mohammad Ali Bigdeli in 1991 and her Ph.D. degree in asymmetric synthesis (Biotransformation) from Laval University, Quebec, Canada under the supervision of Professor Chenevert, in 2000. She is Full Professor of Organic Chemistry in the chemistry department of Alzahra University. Her research interests include organic synthesis, heterocyclic synthesis, asymmetric synthesis, natural products synthesis, synthetic methodology and applications of nano-heterogeneous catalysts in multicomponent reactions.

Book preview

Metal-Free Synthetic Organic Dyes

Ghodsi Mohammadi Ziarani

Razieh Moradi

Negar Lashgari

Alzahra University, Tehran, Iran

Hendrik G. Kruger

University of KwaZulu-Natal, Durban, South Africa

Table of Contents

Cover image

Title page

Copyright

Biography

Acknowledgments

Chapter 1. Introduction and Importance of Synthetic Organic Dyes

Chapter 2. Anthraquinone Dyes

2.1. Synthesis of Anthraquinone Dyes

2.2. Application of Anthraquinone Dyes

Chapter 3. Amine Dyes

3.1. Synthesis of Amine Dyes

3.2. Application of Amine Dyes

Chapter 4. Azo Dyes

4.1. Synthesis of Azo Dyes

4.2. Application of Azo Dyes

Chapter 5. BODIPY Dyes

5.1. Synthesis of Boron Dipyrromethene Dyes

5.2. Application of Boron Dipyrromethene Dyes

Chapter 6. Carbazole Dyes

6.1. Synthesis of Carbazole Dyes

6.2. Application of Carbazole Dyes

Chapter 7. Coumarin Dyes

7.1. Synthesis of Coumarin Dyes

7.2. Application of Coumarin Dyes

Chapter 8. Cyanine Dyes

8.1. Synthesis of Cyanine Dyes

8.2. Application of Cyanine Dyes

Chapter 9. Fluorene Dyes

9.1. Synthesis of Fluorene Dyes

9.2. Application of Fluorene Dyes

Chapter 10. Fluorescein Dyes

10.1. Synthesis of Fluorescein Dyes

10.2. Application of Fluorescein Dyes

Chapter 11. Imide Dyes

11.1. Synthesis of Imide Dyes

11.2. Application of Imide Dyes

Chapter 12. Oxazine Dyes

12.1. Synthesis and Application of Oxazine Dyes

Chapter 13. Phenothiazine Dyes

13.1. Synthesis of Phenothiazine Dyes

13.2. Application of Phenothiazine Dyes

Chapter 14. Rhodamine Dyes

14.1. Synthesis of Rhodamine Dyes

14.2. Application of Rhodamine Dyes

Chapter 15. Squaraine Dyes

15.1. Synthesis of Squaraine Dyes

Chapter 16. Thiophene Dyes

16.1. Synthesis of Thiophene Dyes

16.2. Application of Thiophene Dyes

Chapter 17. Triazine Dyes

17.1. Synthesis of Triazine Dyes

17.2. Application of Triazine Dyes

Chapter 18. The Dyes Based on Several Chromophores

18.1. Synthesis of Dyes Based on Several Chromophores

18.2. Application of Dyes Based on Several Chromophores

Chapter 19. Miscellaneous Dyes

19.1. Synthesis of Miscellaneous Dyes

19.2. Application of Miscellaneous Dyes

Chapter 20. Conclusions

Abbreviations

Index

Copyright

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Biography

Ghodsi Mohammadi Ziarani was born in Iran, in 1964. She received her BSc degree in Chemistry from Teacher Training University, Tehran, Iran, in 1987, her MSc degree in Organic Chemistry from the Teacher Training University, Tehran, Iran, under the supervision of Professor Jafar Asgarin and Professor Mohammad Ali Bigdeli in 1991, and her PhD degree in asymmetric synthesis (Biotransformation) from Laval University, Quebec, Canada under the supervision of Professor Chenevert, in 2000. She is Full Professor of Organic Chemistry in the chemistry department of Alzahra University. Her research interests include organic synthesis, heterocyclic synthesis, asymmetric synthesis, natural products synthesis, synthetic methodology, and applications of nanoheterogeneous catalysts in multicomponent reactions.

Razieh Moradi was born in 1990 in Delfan, Lorestan, Iran. She obtained her BSc degree in Chemistry from the University of Lorestan (2012) and her MSc degree in Organic Chemistry at Alzahra University under the supervision of Dr. Ghodsi Mohammadi Ziarani. She is currently a PhD student in Organic Chemistry at Alzahra University under the supervision of Dr. Ghodsi Mohammadi Ziarani. Her research field is on the synthesis of heterocyclic compounds, synthesis of organic dyes, and application of nanoheterogeneous catalysts in organic synthesis and multicomponent reactions.

Negar Lashgari was born in 1985 in Tehran, Iran. She received her BSc degree in Applied Chemistry from Kharazmi University, Karaj, Iran (2008) and her MSc degree in Organic Chemistry at Alzahra University, Tehran, Iran (2011) under the supervision of Dr. Ghodsi Mohammadi Ziarani. She obtained her PhD degree in Nano Chemistry from University of Tehran under the supervision of Dr. Alireza Badiei and Dr. Ghodsi Mohammadi Ziarani in 2017. Her research field is synthesis and functionalization of mesoporous silica materials and their application as nanoheterogeneous catalysts in multicomponent reactions and also as chemosensors for detection of various anions and cations.

Gert (H.G.) Kruger graduated from Potchefstroom University, South Africa, in 1996 under the supervision of Frans (F.J.C.) Martins and Attie (A.M.) Viljoen. His PhD lineage is traced back to Rudolf Criegee (Wurzburg) via Johan Dekker (Karlsruhe). The Dekkers introduced cage chemistry to South Africa, and Kruger actively pursues the synthesis, computational chemistry, and biological application of cage compounds at the Catalysis and Peptide Research Unit, University of KwaZulu Natal as a research professor.

Acknowledgments

We are grateful for financial support from the Research Council of Alzahra University.

Chapter 1

Introduction and Importance of Synthetic Organic Dyes

Abstract

Synthetic dyes, manufactured from organic molecules, are more and more playing important roles in our modern life with applications in both industry (e.g., paint industry) and scientific laboratories (e.g., fluorescent tracers and photoredox catalysts). A plethora of strategies were invented by chemists to facilitate the synthesis of complex synthetic organic dyes. This book presents comprehensive information on the respective synthetic organic dyes. In this regard, a variety of dyes, including anthraquinones, aryl amines, azo dyes, BODIPY, carbazoles, cyanines, fluoresceins, oxazines, phenothiazines, rhodamines, squaraines, thiophene dyes, etc., were collected and discussed.

Keywords

Dye-sensitized solar cells; Industry; Organic dyes; Photosensitizer; Synthetic dyes

Chapter Outline

References

Synthetic dyes are manufactured from organic molecules. Before the discovery of synthetic dyes in 1856, the majority of natural dyes were prepared from plant sources: roots, berries, bark, leaves, wood, fungi, and lichens (Fig. 1.1) [1–4]. Batches of natural dyes were never exactly alike in hue and intensity, whereas synthetic dyestuffs can be manufactured consistently (Fig. 1.2) [5–10]. These dyes are made from synthetic resources such as chemicals, petroleum by-products, and earth minerals. The first human-made organic aniline dye, mauveine, was discovered by William Henry Perkin in 1856 [11], the result of a failed attempt in total synthesis of quinine. Since then, thousands of synthetic dyes have been prepared [12,13].

Synthetic dyes have been widely used in supramolecular chemistry not only to probe fundamental chemical interactions but also as components of functional materials [14–20]. Many of them have been widely utilized as fluorescent tracers in medicinal [13,21–23] and biological [24–30] applications and tumor-infected tissues tracers [31–33]. Organic dyes were also applied as photoredox catalysts in organic synthesis [34–37], laser [38–47], nanofiber [48], and in the paint industry [49–52].

During the past decade, numerous research attempts have been made on exploring new photosensitizers in the development of dye-sensitized solar cells (DSSCs). In the last decade, DSSCs have received considerable attention as one of the most promising new renewable photovoltaic cells alternative to conventional solid-state cells because of their advantageous properties, including low cost, environmental compatibility, and simplicity of the fabrication process. In recent years, metal-free organic dyes have been central in the development of DSSCs and are known to improve photovoltaic performance of DSSCs. In this regard, a variety of metal-free organic sensitizers have been developed [53–90].

Metal-free organic dyes offer the advantages of superior molar extinction coefficients, lower cost, and large diversity of molecular structures. Several versatile metal-free organic dyes have been synthesized over the past decade. These novel photosensitizers have incorporated different organic groups such as coumarins [91], cyanines [92,93], hemicyanines [94], indolines [95], triphenylamines [96], bis(dimethylfluorenyl) aminophenyls [97], phenothiazines [98,99], carbazoles [100], polyenes [101], fluorenes [102], and many others.

Figure 1.1  Representative natural dyes.

Figure 1.2  Representative synthetic dyes.

Because of the widespread use of organic dyes and also tremendous interest of researchers in the area of synthetic organic dyes, and since there is no comprehensive book on the synthesis of different organic dyes, this book aims to review the synthetic organic dyes by classifying them based on their chemical structure and describing the synthesis and application of these structures. To make it easier for the reader to find the respective synthetic organic dyes, we chose to arrange this book based on the names of the organic dyes in alphabetical order. As far as possible, we have also indicated the color of the respective dyes in the various figures and schemes. Because of the vast area of organic synthetic dyes, it is virtually impossible to present all examples here; however, we attempted to summarize the most important structures and functional groups.

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Chapter 2

Anthraquinone Dyes

Abstract

Anthraquinone (AQ) derivatives