POLYMETHYLENE DYES FROM 2-METHYLINDOLO(3,2-B)THIAZOLO(5,4-D)QUINOXALINES HAVING SUBSTITUENTS AT THE NITROGEN ATOM OF THE INDOLE RING

POLYMETHYLENE DYES FROM 2-METHYLINDOLO(3,2-B)THIAZOLO(5,4-D)QUINOXALINES HAVING SUBSTITUENTS AT THE NITROGEN ATOM OF THE INDOLE RING

Condensation of isatin with N-methylisatin, N-ethyl, N-propyl, N-butyl, N-phenyl, N-benzoyl and 5-nitroisatin with 2-methyl 5,6-diami­nobenzthiazole gave 2-methyl-indolo(3,2-b)thiazolo(5,4-d)quinoxalines with a substituted nitrogen atom in the indole ring. When they are heated with alkyltosylates, q...

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Date:2024
Main Authors: Shulga, Sergii, Shulga, Oksana
Format: Article
Language:English
Published: V.I.Vernadsky Institute of General and Inorganic Chemistry 2024
Online Access:https://ucj.org.ua/index.php/journal/article/view/630
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spelling oai:ojs2.1444248.nisspano.web.hosting-test.net:article-6302025-01-28T08:21:13Z POLYMETHYLENE DYES FROM 2-METHYLINDOLO(3,2-B)THIAZOLO(5,4-D)QUINOXALINES HAVING SUBSTITUENTS AT THE NITROGEN ATOM OF THE INDOLE RING Shulga, Sergii Shulga, Oksana 2-methylindolo(3,2-b)thiazolo­(5,4-d)quinoxaline, diaminobenzthiazole, isa­tin, polymethine dyes. Condensation of isatin with N-methylisatin, N-ethyl, N-propyl, N-butyl, N-phenyl, N-benzoyl and 5-nitroisatin with 2-methyl 5,6-diami­nobenzthiazole gave 2-methyl-indolo(3,2-b)thiazolo(5,4-d)quinoxalines with a substituted nitrogen atom in the indole ring. When they are heated with alkyltosylates, quaternary salts are formed from which various cyanine dyes are synthesized: styryls, monomethinecyani­nes, asymmetric carbocyanines. The absorption maxima of each dye were determined and analyzed, and the results of elemental analysis for Carbon, Hydrogen, and Sulfur were given. The influence of substituents at the nitrogen of the indole ring on the absorption maxima of the synthesized dyes was established. During the transition from methyl to ethyl and further to propyl, butyl, phenyl, and benzoyl, a bathochromic shift of the absorption maximum of the dye is observed by several nanometers (for styrenes 2–6 nm, for monomethinecyanines 1–10 nm and asymmetric carbocyanines 2–7 nm) of the next dye compared to the previous one. The greatest influence of the absorption maxima bathochromic shift of dyes (up to 7 nm) belongs to N-substituents in the phenyl indole ring, benzoyl, and nitro group. The absorption maxima of the obtained cyanine dyes in an acidic environment show a strong bathochromic shift (up to 93 nm) compared to neutral solutions, which can be explained by an increase in the conjugation chain due to the one protonation of the phenazine cycle nitrogen atoms. It can be seen that N-phenyl, N-benzoyl, and the nitro group in the 5-position of the indole ring give the largest bathochromic shift from the analysis of the dyes absorption maxima. Thus, in the presence of phenyl and benzoyl in the indole ring, the absorption maxima are 456 and 460 nm, respectively, against the unsubstituted nitrogen atom in the indole ring at 440 nm. V.I.Vernadsky Institute of General and Inorganic Chemistry 2024-02-26 Article Article Organic chemistry Органическая xимия Органічна xімія application/pdf https://ucj.org.ua/index.php/journal/article/view/630 10.33609/2708-129X.90.1.2024.26-37 Ukrainian Chemistry Journal; Vol. 90 No. 1 (2024): Ukrainian Chemistry Journal; 26-35 Украинский химический журнал; Том 90 № 1 (2024): Ukrainian Chemistry Journal; 26-35 Український хімічний журнал; Том 90 № 1 (2024): Ukrainian Chemistry Journal; 26-35 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/630/316
institution Ukrainian Chemistry Journal
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datestamp_date 2025-01-28T08:21:13Z
collection OJS
language English
topic_facet 2-methylindolo(3,2-b)thiazolo­(5,4-d)quinoxaline
diaminobenzthiazole
isa­tin
polymethine dyes.
format Article
author Shulga, Sergii
Shulga, Oksana
spellingShingle Shulga, Sergii
Shulga, Oksana
POLYMETHYLENE DYES FROM 2-METHYLINDOLO(3,2-B)THIAZOLO(5,4-D)QUINOXALINES HAVING SUBSTITUENTS AT THE NITROGEN ATOM OF THE INDOLE RING
author_facet Shulga, Sergii
Shulga, Oksana
author_sort Shulga, Sergii
title POLYMETHYLENE DYES FROM 2-METHYLINDOLO(3,2-B)THIAZOLO(5,4-D)QUINOXALINES HAVING SUBSTITUENTS AT THE NITROGEN ATOM OF THE INDOLE RING
title_short POLYMETHYLENE DYES FROM 2-METHYLINDOLO(3,2-B)THIAZOLO(5,4-D)QUINOXALINES HAVING SUBSTITUENTS AT THE NITROGEN ATOM OF THE INDOLE RING
title_full POLYMETHYLENE DYES FROM 2-METHYLINDOLO(3,2-B)THIAZOLO(5,4-D)QUINOXALINES HAVING SUBSTITUENTS AT THE NITROGEN ATOM OF THE INDOLE RING
title_fullStr POLYMETHYLENE DYES FROM 2-METHYLINDOLO(3,2-B)THIAZOLO(5,4-D)QUINOXALINES HAVING SUBSTITUENTS AT THE NITROGEN ATOM OF THE INDOLE RING
title_full_unstemmed POLYMETHYLENE DYES FROM 2-METHYLINDOLO(3,2-B)THIAZOLO(5,4-D)QUINOXALINES HAVING SUBSTITUENTS AT THE NITROGEN ATOM OF THE INDOLE RING
title_sort polymethylene dyes from 2-methylindolo(3,2-b)thiazolo(5,4-d)quinoxalines having substituents at the nitrogen atom of the indole ring
description Condensation of isatin with N-methylisatin, N-ethyl, N-propyl, N-butyl, N-phenyl, N-benzoyl and 5-nitroisatin with 2-methyl 5,6-diami­nobenzthiazole gave 2-methyl-indolo(3,2-b)thiazolo(5,4-d)quinoxalines with a substituted nitrogen atom in the indole ring. When they are heated with alkyltosylates, quaternary salts are formed from which various cyanine dyes are synthesized: styryls, monomethinecyani­nes, asymmetric carbocyanines. The absorption maxima of each dye were determined and analyzed, and the results of elemental analysis for Carbon, Hydrogen, and Sulfur were given. The influence of substituents at the nitrogen of the indole ring on the absorption maxima of the synthesized dyes was established. During the transition from methyl to ethyl and further to propyl, butyl, phenyl, and benzoyl, a bathochromic shift of the absorption maximum of the dye is observed by several nanometers (for styrenes 2–6 nm, for monomethinecyanines 1–10 nm and asymmetric carbocyanines 2–7 nm) of the next dye compared to the previous one. The greatest influence of the absorption maxima bathochromic shift of dyes (up to 7 nm) belongs to N-substituents in the phenyl indole ring, benzoyl, and nitro group. The absorption maxima of the obtained cyanine dyes in an acidic environment show a strong bathochromic shift (up to 93 nm) compared to neutral solutions, which can be explained by an increase in the conjugation chain due to the one protonation of the phenazine cycle nitrogen atoms. It can be seen that N-phenyl, N-benzoyl, and the nitro group in the 5-position of the indole ring give the largest bathochromic shift from the analysis of the dyes absorption maxima. Thus, in the presence of phenyl and benzoyl in the indole ring, the absorption maxima are 456 and 460 nm, respectively, against the unsubstituted nitrogen atom in the indole ring at 440 nm.
publisher V.I.Vernadsky Institute of General and Inorganic Chemistry
publishDate 2024
url https://ucj.org.ua/index.php/journal/article/view/630
work_keys_str_mv AT shulgasergii polymethylenedyesfrom2methylindolo32bthiazolo54dquinoxalineshavingsubstituentsatthenitrogenatomoftheindolering
AT shulgaoksana polymethylenedyesfrom2methylindolo32bthiazolo54dquinoxalineshavingsubstituentsatthenitrogenatomoftheindolering
first_indexed 2025-09-24T17:43:55Z
last_indexed 2025-09-24T17:43:55Z
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