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Isomerization and Properties of Isomers of Carbocyanine Dyes

N.M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, Kosygin Str. 4, 119334 Moscow, Russia
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Received: 20 November 2018 / Accepted: 26 November 2018 / Published: 20 March 2019
One of the important features of polymethine (cyanine) dyes is isomerization about one of C–C bonds of the polymethine chain. In this review, spectral properties of the isomers, photoisomer-ization and thermal back isomerization of carbocyanine dyes, mostly meso-substituted carbocy-anine dyes, are considered. meso-Alkyl-substituted thiacarbocyanine dyes are present in polar solvents mainly as cis isomers and, hence, exhibit no photoisomerization, whereas in nonpolar solvents, in which the dyes are in the trans form, photoisomerization takes place. In contrast, the meso-substituted dyes 3,3′-dimethyl-9-phenylthiacarbocyanine and 3,3′-diethyl-9-(2-hydroxy-4-methoxyphenyl)thiacarbocyanine occur as trans isomers and exhibit photoisomerization in both polar and nonpolar solvents. The behavior of these dyes may be ex-plained by the fact that the phenyl ring of the substituent in their molecules can be twisted at some angle, removing the substituent from the plane of the molecule and reducing its steric ef-fect on the conformation of the trans isomer. In some cases, photoisomerization of cis isomers of meso-substituted carbocyanine dyes is also observed (for some meso-alkyl-substituted dyes com-plexed with DNA and chondroitin-4-sulfate; for 3,3′-diethyl-9-methoxythiacarbocyanine in moderate polarity solvents). The cycle photoisomerization–thermal back isomerization of cya-nine dyes can be used in various systems of information storage and deserves further investiga-tion using modern research methods. View Full-Text
Keywords: carbocyanine dyes; isomerization; trans and cis isomers; meso-substituted cyanines carbocyanine dyes; isomerization; trans and cis isomers; meso-substituted cyanines
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MDPI and ACS Style

Pronkin, P.; Tatikolov, A. Isomerization and Properties of Isomers of Carbocyanine Dyes. Sci 2019, 1, 19. https://doi.org/10.3390/sci1010019

AMA Style

Pronkin P, Tatikolov A. Isomerization and Properties of Isomers of Carbocyanine Dyes. Sci. 2019; 1(1):19. https://doi.org/10.3390/sci1010019

Chicago/Turabian Style

Pronkin, Pavel, and Alexander Tatikolov. 2019. "Isomerization and Properties of Isomers of Carbocyanine Dyes" Sci 1, no. 1: 19. https://doi.org/10.3390/sci1010019

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