Chapter 1
Polymethine Dyes
Masaki Matsui
Abstract Polymethine dyes consist of heteroaromatic end and linkage groups. They
are classified into cyanines, merocyanines, and oxonols. Their UV–Vis and nearinfrared (NIR) absorption band are affected by the heteroaromatics and linkage
groups. The change in the absorption band of polymethine dyes by aggregate formation has been explained by the molecular exciton coupling theory. Polymethine dyes
have been used as data recording materials. Polymethine dyes can be used as sensitizers in dye-sensitized solar cells. Though usual dyes are solid, liquid trimethine
dyes have been reported. The fluorescence intensity of the liquid trimethine dyes is
drastically enhanced in liquid nitrogen.
Keywords Synthesis · UV–vis absorption band · Data recording materials ·
Sensitizers
1.1 Introduction
In the nineteenth century, it was strongly desired to prepare “Quinine” which acts
as an antimalarial drug. It was known that an antimalarial compound “Cinchonine”
was contained in the sap of Cinchona officinalis. An English chemist, G. Williams,
isolated magnificent blue material from “Cinchonine” in 1856. Later, the structure
was proved to be the mixture of mono- and trimethine dyes 1.1 and 1.2 as shown
in Fig. 1.1. This material was named cyanine (cyanos = blue). It is well known that
W. H. Perkin discovered Mauve or Mauveine in 1856. However, the discovery of
cyanine is hardly known, probably due to the fact that cyanine was very weak upon
light irradiation to become a commercial dye for coloration purpose.
In 1873, a German chemist, H. W. Vogel, found that cyanine dyes could enhance
the photosensitivity in photography. As World War I broke out in 1914, it was desired
to develop the studies on the sensitizers in the field of photography. An English
chemist, W. H. Miles, further developed the studies on cyanine dyes.
M. Matsui (B)
Gifu University, Gifu, Japan
e-mail: matsuimasaki_family@nifty.com
© Springer Nature Singapore Pte Ltd. 2021
Y. Ooyama and S. Yagi (eds.), Progress in the Science of Functional Dyes,
https://doi.org/10.1007/978-981-33-4392-4_1
3
Polymethine Dyes
Masaki Matsui
Abstract Polymethine dyes consist of heteroaromatic end and linkage groups. They
are classified into cyanines, merocyanines, and oxonols. Their UV–Vis and nearinfrared (NIR) absorption band are affected by the heteroaromatics and linkage
groups. The change in the absorption band of polymethine dyes by aggregate formation has been explained by the molecular exciton coupling theory. Polymethine dyes
have been used as data recording materials. Polymethine dyes can be used as sensitizers in dye-sensitized solar cells. Though usual dyes are solid, liquid trimethine
dyes have been reported. The fluorescence intensity of the liquid trimethine dyes is
drastically enhanced in liquid nitrogen.
Keywords Synthesis · UV–vis absorption band · Data recording materials ·
Sensitizers
1.1 Introduction
In the nineteenth century, it was strongly desired to prepare “Quinine” which acts
as an antimalarial drug. It was known that an antimalarial compound “Cinchonine”
was contained in the sap of Cinchona officinalis. An English chemist, G. Williams,
isolated magnificent blue material from “Cinchonine” in 1856. Later, the structure
was proved to be the mixture of mono- and trimethine dyes 1.1 and 1.2 as shown
in Fig. 1.1. This material was named cyanine (cyanos = blue). It is well known that
W. H. Perkin discovered Mauve or Mauveine in 1856. However, the discovery of
cyanine is hardly known, probably due to the fact that cyanine was very weak upon
light irradiation to become a commercial dye for coloration purpose.
In 1873, a German chemist, H. W. Vogel, found that cyanine dyes could enhance
the photosensitivity in photography. As World War I broke out in 1914, it was desired
to develop the studies on the sensitizers in the field of photography. An English
chemist, W. H. Miles, further developed the studies on cyanine dyes.
M. Matsui (B)
Gifu University, Gifu, Japan
e-mail: matsuimasaki_family@nifty.com
© Springer Nature Singapore Pte Ltd. 2021
Y. Ooyama and S. Yagi (eds.), Progress in the Science of Functional Dyes,
https://doi.org/10.1007/978-981-33-4392-4_1
3