Synthesis and Spectral Properties of Iodine-Substituted Dyes Based on Benzothiazolium Salts

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Abstract

Two series of new thiacarbocyanines with iodine atoms in the donor and/or acceptor block have been synthesized. The absorption spectra of the iodinated dyes in the region of singlet-singlet S0-S1 and singlet-triplet S0-T1 transitions are investigated. The introduction of iodine atoms into the dye structures leads to a red shift of the absorption maximum, regardless of the position of iodine in the molecule. For dyes with two or more iodine atoms, a low-intensity long-wave absorption shoulder in the region from 650 to 1000 nm is detected, which corresponds to singlet-triplet absorption.

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About the authors

I. A. Malakhov

N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences; Novosibirsk National Research State University

Author for correspondence.
Email: ona20083@mail.ru
Russian Federation, Novosibirsk; Novosibirsk

N. A. Orlova

N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: ona20083@mail.ru
Russian Federation, Novosibirsk

V. V. Shelkovnikov

N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences; Institute of Chemical Biology and Fundamental Medicine of the Siberian Branch of the Russian Academy of Sciences

Email: ona20083@mail.ru
Russian Federation, Novosibirsk; Novosibirsk

E. V. Vasilyev

N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: ona20083@mail.ru
Russian Federation, Novosibirsk

A. A. Chernonosov

Institute of Chemical Biology and Fundamental Medicine of the Siberian Branch of the Russian Academy of Sciences

Email: ona20083@mail.ru
Russian Federation, Novosibirsk

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Supplementary files

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2. Fig. 1. Iodine-substituted dyes 17–21 with a 5-(methylthio)thienyl donor fragment

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3. Fig. 2. EAS of dimethylaminobenzylidene-containing dyes 14–16 in chloroform (main transition)

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4. Fig. 3. EAS of 5-(methylthio)thiophenylene-containing dyes 17–21 in chloroform (main transition)

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5. Fig. 4. Spectral curves of molar extinction of 4-(dimethylamino)benzylidene-containing dyes 14–16 in acetonitrile, presented in a logarithmic ordinate scale

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6. Fig. 5. Spectral molar extinction curves of 5-(methylthio)thiophenylene-containing dyes 17–21 in acetonitrile, presented in a logarithmic ordinate scale

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7. Scheme 1

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8. Scheme 2

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9. Scheme 3

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10. Scheme 4

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11. Scheme 5

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