Metal-Free Synthetic Organic Dyes

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

• Publisher: Elsevier
• Year: 2018
• ISBN:
  9780128156483
• Topic: Ciencias físicas
• Subtopic: Química orgánica

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

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

1. 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.

References

[1] Brightman R. Perkin and the dyestuffs industry in Britain. Nature. 1956;177:805–856.

[2] Vankar P.S, Shanker R, Mahanta D, Tiwari S. Ecofriendly sonicator dyeing of cotton with Rubia cordifolia Linn. using biomordant. Dyes Pigment. 2008;76(1):207–212.

[3] McGovern P.E, Michel R.H. Royal purple dye: tracing the chemical origins of the industry. Anal Chem. 1985;57(14):1514–1522.

[4] Hunger K, Herbst W. Pigments, organic. In: Ullmann’s encyclopedia of industrial chemistry. Weinheim: Wiley-VCH; 2012.

[5] Macleod L.C, Allen C.F.H. Benzanthrone. Org Synth. 1934;2:62–69.

[6] Clarke H.T, Kirner W.R. Methyl red. Org Synth. 1941;1:374–375. .

[7] Caro H, [Inventor]. U.S. Patent, assignee. Improvement in the production of dye-stuffs from methyl-aniline patent U. S. Patent 204796 A; June 11, 1878.

[8] Fittig R. Ueber einen neuen Kohlenwasserstoff aus dem diphenylenketon. Ber Dtsch Chem Ges. 1873;6(1):187.

[9] Schäfer F.P. Dye lasers. 3rd ed. Berlin: Springer-Verlag; 1990.

[10] Duarte F.J, Hillman L.W. Dye laser principles. New York: Academic; 1990.

[11] Perkin WH, [Inventor]. Dyeing fabrics patent British Patent 1984; 1856.

[12] Hunger K. Industrial dyes: chemistry, properties, applications. Weinheim: Wiley-VCH; 2003.

[13] Zollinger H. Color chemistry. Synthesis, properties and applications of organic dyes and pigments. Weinheim: Wiley-VCH; 2003.

[14] Arunkumar E, Forbes C.C, Smith B.D. Improving the properties of organic dyes by molecular encapsulation. Eur J Org Chem. 2005;2005(19):4051–4059.

[15] Würthner F, Kaiser T.E, Saha-Möller C.R. J-aggregates: from serendipitous discovery to supramolecular engineering of functional dye materials. Angew Chem Int Ed. 2011;50(15):3376–3410.

[16] Benvin A.L, Creeger Y, Fisher G.W, Ballou B, Waggoner A.S, Armitage B.A. Fluorescent DNA nanotags: supramolecular fluorescent labels based on intercalating dye arrays assembled on nanostructured DNA templates. J Am Chem Soc. 2007;129(7):2025–2034.

[17] Hannah K.C, Armitage B.A. DNA-templated assembly of helical cyanine dye aggregates: a supramolecular chain polymerization. Acc Chem Res. 2004;37(11):845–853.

[18] Von Berlepsch H, Böttcher C, Ouart A, Burger C, Dähne S, Kirstein S. Supramolecular structures of J-aggregates of carbocyanine dyes in solution. J Phys Chem B. 2000;104(22):5255–5262.

[19] Dsouza R.N, Pischel U, Nau W.M. Fluorescent dyes and their supramolecular host/guest complexes with macrocycles in a...