SYNTHESIS AND ABSORPTION SPECTRA OF INDOTRICARBOCYANINE DYES WITH ELECTRON-DONATING GROUPS IN THE MESO-POSITION OF THE POLYMETHINE CHAIN

SYNTHESIS AND ABSORPTION SPECTRA OF INDOTRICARBOCYANINE DYES WITH ELECTRON-DONATING GROUPS IN THE MESO-POSITION OF THE POLYMETHINE CHAIN

Recently, a large number of studies have been dedicated to chemistry and physical stu­dies of polymethine dyes, especially to the functio­na­lized symmetrical heptamethinecyanines based on the indole derivatives. Due to their unique and versatile spectral properties, which lie in the near infrared r...

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Дата:2023
Автори: Sharanov, Illya, Slominskii, Yuriy
Формат: Стаття
Мова:English
Опубліковано: V.I.Vernadsky Institute of General and Inorganic Chemistry 2023
Онлайн доступ:https://ucj.org.ua/index.php/journal/article/view/534
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Назва журналу:Ukrainian Chemistry Journal

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Ukrainian Chemistry Journal
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spelling oai:ojs2.1444248.nisspano.web.hosting-test.net:article-5342023-05-31T08:33:51Z SYNTHESIS AND ABSORPTION SPECTRA OF INDOTRICARBOCYANINE DYES WITH ELECTRON-DONATING GROUPS IN THE MESO-POSITION OF THE POLYMETHINE CHAIN Sharanov, Illya Slominskii, Yuriy cyanine dyes, indoheptamethinecyanines, polymethine chromophore, donor substituents, bridging groups. Recently, a large number of studies have been dedicated to chemistry and physical stu­dies of polymethine dyes, especially to the functio­na­lized symmetrical heptamethinecyanines based on the indole derivatives. Due to their unique and versatile spectral properties, which lie in the near infrared region (NIR), meso-substituted indotricarbocyanine dyes are widely used in various physical and biological fields. In the present work, we have developed methods of synthesis of a series of indotricarbocyanine dyes with di- and trimethylene bridging groups in the γ,γ'-positions and donor substituents in the meso-position of the polymethine chromophore and studied their effects on the spectral properties of the dyes. The obtained data indicated that the change of the substituent in the meso-position of the chromophore and the presence of a poly­me­thylene bridging groups allow to vary signi­ficantly the absorption maxima of the synthesized indoheptamethinecyanine dyes without altering the length of the polymethine chain. It was shown that the electron-donating nitrogen-containing substituents lead, according to the Forster-Dewar-Knott rule, to a hypsochromic shifts of the absorption maxima. However, it was found that the methoxy group in the meso-position of the polymethine chromophore in some cases exhibited unexpected "acceptor" properties due to a certain steric hindrance, resulting in a red shift of the absorption band, in contrast to the other donor substituents. Additionally, the effects of the insertion of di- and trimethylene bridging groups to the polymethine chain of the cyanine dyes on their spectral properties were studied.  The synthesized meso-substituted indotricarbocyanines demonstrated significant solvatochromism and spectral properties that lie in the red and near-infrared regions. V.I.Vernadsky Institute of General and Inorganic Chemistry 2023-03-24 Article Article Organic chemistry Органическая xимия Органічна xімія application/pdf https://ucj.org.ua/index.php/journal/article/view/534 10.33609/2708-129X.89.02.2023.109-124 Ukrainian Chemistry Journal; Vol. 89 No. 2 (2023): Ukrainian Chemistry Journal; 109-124 Украинский химический журнал; Том 89 № 2 (2023): Ukrainian Chemistry Journal; 109-124 Український хімічний журнал; Том 89 № 2 (2023): Український хімічний журнал; 109-124 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/534/270
institution Ukrainian Chemistry Journal
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datestamp_date 2023-05-31T08:33:51Z
collection OJS
language English
topic_facet cyanine dyes
indoheptamethinecyanines
polymethine chromophore
donor substituents
bridging groups.
format Article
author Sharanov, Illya
Slominskii, Yuriy
spellingShingle Sharanov, Illya
Slominskii, Yuriy
SYNTHESIS AND ABSORPTION SPECTRA OF INDOTRICARBOCYANINE DYES WITH ELECTRON-DONATING GROUPS IN THE MESO-POSITION OF THE POLYMETHINE CHAIN
author_facet Sharanov, Illya
Slominskii, Yuriy
author_sort Sharanov, Illya
title SYNTHESIS AND ABSORPTION SPECTRA OF INDOTRICARBOCYANINE DYES WITH ELECTRON-DONATING GROUPS IN THE MESO-POSITION OF THE POLYMETHINE CHAIN
title_short SYNTHESIS AND ABSORPTION SPECTRA OF INDOTRICARBOCYANINE DYES WITH ELECTRON-DONATING GROUPS IN THE MESO-POSITION OF THE POLYMETHINE CHAIN
title_full SYNTHESIS AND ABSORPTION SPECTRA OF INDOTRICARBOCYANINE DYES WITH ELECTRON-DONATING GROUPS IN THE MESO-POSITION OF THE POLYMETHINE CHAIN
title_fullStr SYNTHESIS AND ABSORPTION SPECTRA OF INDOTRICARBOCYANINE DYES WITH ELECTRON-DONATING GROUPS IN THE MESO-POSITION OF THE POLYMETHINE CHAIN
title_full_unstemmed SYNTHESIS AND ABSORPTION SPECTRA OF INDOTRICARBOCYANINE DYES WITH ELECTRON-DONATING GROUPS IN THE MESO-POSITION OF THE POLYMETHINE CHAIN
title_sort synthesis and absorption spectra of indotricarbocyanine dyes with electron-donating groups in the meso-position of the polymethine chain
description Recently, a large number of studies have been dedicated to chemistry and physical stu­dies of polymethine dyes, especially to the functio­na­lized symmetrical heptamethinecyanines based on the indole derivatives. Due to their unique and versatile spectral properties, which lie in the near infrared region (NIR), meso-substituted indotricarbocyanine dyes are widely used in various physical and biological fields. In the present work, we have developed methods of synthesis of a series of indotricarbocyanine dyes with di- and trimethylene bridging groups in the γ,γ'-positions and donor substituents in the meso-position of the polymethine chromophore and studied their effects on the spectral properties of the dyes. The obtained data indicated that the change of the substituent in the meso-position of the chromophore and the presence of a poly­me­thylene bridging groups allow to vary signi­ficantly the absorption maxima of the synthesized indoheptamethinecyanine dyes without altering the length of the polymethine chain. It was shown that the electron-donating nitrogen-containing substituents lead, according to the Forster-Dewar-Knott rule, to a hypsochromic shifts of the absorption maxima. However, it was found that the methoxy group in the meso-position of the polymethine chromophore in some cases exhibited unexpected "acceptor" properties due to a certain steric hindrance, resulting in a red shift of the absorption band, in contrast to the other donor substituents. Additionally, the effects of the insertion of di- and trimethylene bridging groups to the polymethine chain of the cyanine dyes on their spectral properties were studied.  The synthesized meso-substituted indotricarbocyanines demonstrated significant solvatochromism and spectral properties that lie in the red and near-infrared regions.
publisher V.I.Vernadsky Institute of General and Inorganic Chemistry
publishDate 2023
url https://ucj.org.ua/index.php/journal/article/view/534
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AT slominskiiyuriy synthesisandabsorptionspectraofindotricarbocyaninedyeswithelectrondonatinggroupsinthemesopositionofthepolymethinechain
first_indexed 2025-09-24T17:43:49Z
last_indexed 2025-09-24T17:43:49Z
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