SOLVATOCHROMIC PROPERTIES OF SOME 6,7-DIHYDROXYBENZOPYRYLLIUM PERCHLORATE DERIVATIVES
The creation of new reagents based on benzopyrylium derivatives with improved chemical-analytical characteristics is of interest because their preparative synthesis is relatively simple and consists in the condensation of triatomic phenols with β-dicarbonyl compounds. Benzopyryllium derivatives are...
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| Datum: | 2023 |
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V.I.Vernadsky Institute of General and Inorganic Chemistry
2023
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oai:ojs2.1444248.nisspano.web.hosting-test.net:article-5792023-12-22T17:01:01Z SOLVATOCHROMIC PROPERTIES OF SOME 6,7-DIHYDROXYBENZOPYRYLLIUM PERCHLORATE DERIVATIVES Zhukovetska, O spectrophotometry, solvatochromism, 6,7-dihydroxybenzopyrylium derivatives, Hansen parameter, Kamlet-Taft parameter, Gutman’s donor and acceptor numbers. The creation of new reagents based on benzopyrylium derivatives with improved chemical-analytical characteristics is of interest because their preparative synthesis is relatively simple and consists in the condensation of triatomic phenols with β-dicarbonyl compounds. Benzopyryllium derivatives are reactive compounds and are able to redox reactions, complexes formation with polyvalent metal ions, and are also prone to acid-base transformations in solutions. It should be noted separately that hydroxyderivatives of benzopyrylium during complex formation can turn into anhydro bases with a quinoid structure, which leads to a significant bathochromic shift of the absorption band and an increase in the contrast of analytical reactions. The current work is devoted to the study of solvatochromic properties of a number of 6,7-dihydroxybenzopyrylium perchlorate derivatives: 6,7-dihydroxy-2,4-dimethylbenzopyrylium, 6,7-dihydroxy-2-phenyl-4-methylbenzopyrylium and 6,7-dihydroxy-2,4 -diphenylbenzopyrylium. The presented work is a continuation of research on synthesis, acid-base and complexation of 6,7-dihydroxybenzopyrylium derivatives. The influence of the nature of organic solvents was studied using the example of methanol, ethanol, n-propanol, iso-propanol, n-butanol, iso-butanol, n-pentanol, iso-pentanol, n-hexanol, n-heptanol, n-nonanol, decanol, dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, acetonitrile, butyl acetate, toluene, and chloroform. It is shown that when a polar solvent is replaced by a less polar one, a bathochromic shift of the maximum of the absorption band of 6,7-dihydroxybenzopyrylium derivatives is observed, which corresponds to the n→π* electronic transition. It was noted that there is a satisfactory correlation (R = 0.795–0.993) between the position of the maximum absorption of the dye and the values of the Hansen parameter, Kamlet – Taft, donor and acceptor number according to Gutman. V.I.Vernadsky Institute of General and Inorganic Chemistry 2023-09-29 Article Article Organic chemistry Органическая xимия Органічна xімія application/pdf https://ucj.org.ua/index.php/journal/article/view/579 10.33609/2708-129X.89.08.2023.117-126 Ukrainian Chemistry Journal; Vol 89 No 8 (2023): Ukrainian Chemistry Journal; 117-126 Украинский химический журнал; Том 89 № 8 (2023): Ukrainian Chemistry Journal; 117-126 Український хімічний журнал; Том 89 № 8 (2023): Ukrainian Chemistry Journal; 117-126 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/579/296 |
| institution |
Ukrainian Chemistry Journal |
| baseUrl_str |
|
| datestamp_date |
2023-12-22T17:01:01Z |
| collection |
OJS |
| language |
English |
| topic_facet |
spectrophotometry solvatochromism 6,7-dihydroxybenzopyrylium derivatives Hansen parameter Kamlet-Taft parameter Gutman’s donor and acceptor numbers. |
| format |
Article |
| author |
Zhukovetska, O |
| spellingShingle |
Zhukovetska, O SOLVATOCHROMIC PROPERTIES OF SOME 6,7-DIHYDROXYBENZOPYRYLLIUM PERCHLORATE DERIVATIVES |
| author_facet |
Zhukovetska, O |
| author_sort |
Zhukovetska, O |
| title |
SOLVATOCHROMIC PROPERTIES OF SOME 6,7-DIHYDROXYBENZOPYRYLLIUM PERCHLORATE DERIVATIVES |
| title_short |
SOLVATOCHROMIC PROPERTIES OF SOME 6,7-DIHYDROXYBENZOPYRYLLIUM PERCHLORATE DERIVATIVES |
| title_full |
SOLVATOCHROMIC PROPERTIES OF SOME 6,7-DIHYDROXYBENZOPYRYLLIUM PERCHLORATE DERIVATIVES |
| title_fullStr |
SOLVATOCHROMIC PROPERTIES OF SOME 6,7-DIHYDROXYBENZOPYRYLLIUM PERCHLORATE DERIVATIVES |
| title_full_unstemmed |
SOLVATOCHROMIC PROPERTIES OF SOME 6,7-DIHYDROXYBENZOPYRYLLIUM PERCHLORATE DERIVATIVES |
| title_sort |
solvatochromic properties of some 6,7-dihydroxybenzopyryllium perchlorate derivatives |
| description |
The creation of new reagents based on benzopyrylium derivatives with improved chemical-analytical characteristics is of interest because their preparative synthesis is relatively simple and consists in the condensation of triatomic phenols with β-dicarbonyl compounds. Benzopyryllium derivatives are reactive compounds and are able to redox reactions, complexes formation with polyvalent metal ions, and are also prone to acid-base transformations in solutions. It should be noted separately that hydroxyderivatives of benzopyrylium during complex formation can turn into anhydro bases with a quinoid structure, which leads to a significant bathochromic shift of the absorption band and an increase in the contrast of analytical reactions. The current work is devoted to the study of solvatochromic properties of a number of 6,7-dihydroxybenzopyrylium perchlorate derivatives: 6,7-dihydroxy-2,4-dimethylbenzopyrylium, 6,7-dihydroxy-2-phenyl-4-methylbenzopyrylium and 6,7-dihydroxy-2,4 -diphenylbenzopyrylium. The presented work is a continuation of research on synthesis, acid-base and complexation of 6,7-dihydroxybenzopyrylium derivatives. The influence of the nature of organic solvents was studied using the example of methanol, ethanol, n-propanol, iso-propanol, n-butanol, iso-butanol, n-pentanol, iso-pentanol, n-hexanol, n-heptanol, n-nonanol, decanol, dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, acetonitrile, butyl acetate, toluene, and chloroform. It is shown that when a polar solvent is replaced by a less polar one, a bathochromic shift of the maximum of the absorption band of 6,7-dihydroxybenzopyrylium derivatives is observed, which corresponds to the n→π* electronic transition. It was noted that there is a satisfactory correlation (R = 0.795–0.993) between the position of the maximum absorption of the dye and the values of the Hansen parameter, Kamlet – Taft, donor and acceptor number according to Gutman. |
| publisher |
V.I.Vernadsky Institute of General and Inorganic Chemistry |
| publishDate |
2023 |
| url |
https://ucj.org.ua/index.php/journal/article/view/579 |
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