SOLVATOCHROMIC PROPERTIES OF SOME 6,7-DIHYDROXYBENZOPYRYLLIUM PERCHLORATE DERIVATIVES

O. Zhukovetska
{"title":"SOLVATOCHROMIC PROPERTIES OF SOME 6,7-DIHYDROXYBENZOPYRYLLIUM PERCHLORATE DERIVATIVES","authors":"O. Zhukovetska","doi":"10.33609/2708-129x.89.08.2023.117-126","DOIUrl":null,"url":null,"abstract":"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.","PeriodicalId":23394,"journal":{"name":"Ukrainian Chemistry Journal","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2023-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Ukrainian Chemistry Journal","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.33609/2708-129x.89.08.2023.117-126","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0

Abstract

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.
一些 6,7-二羟基苯并吡喃鎓高氯酸盐衍生物的溶解变色特性
基于苯并芘衍生物的新试剂具有更好的化学分析特性,其制备合成相对简单,只需将三原子酚与β-二羰基化合物缩合即可,因此这种试剂的开发备受关注。苯并芘衍生物是活性化合物,能够发生氧化还原反应,与多价金属离子形成络合物,还容易在溶液中发生酸碱转化。需要单独指出的是,苯并芘的羟基衍生物在形成络合物的过程中会变成具有醌结构的氢基,从而导致吸收带发生明显的浴色偏移,并增加分析反应的对比度。目前的工作致力于研究一些 6,7-二羟基苯并吡喃鎓高氯酸盐衍生物的溶解变色特性:6,7-二羟基-2,4-二甲基苯并吡喃鎓、6,7-二羟基-2-苯基-4-甲基苯并吡喃鎓和 6,7-二羟基-2,4-二苯基苯并吡喃鎓。本研究是 6,7-二羟基苯并吡喃rylium 衍生物的合成、酸碱和络合研究的继续。以甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、正戊醇、异戊醇、正己醇、正庚醇、正壬醇、癸醇、二甲基甲酰胺、二甲基亚砜、四氢呋喃、乙腈、乙酸丁酯、甲苯和氯仿为例,研究了有机溶剂性质的影响。研究表明,当极性溶剂被极性较低的溶剂取代时,6,7-二羟基苯并吡喃鎓衍生物吸收带的最大值会发生浴色偏移,这与 n→π* 电子转变相对应。结果表明,染料最大吸收位置与汉森参数值、Kamlet - Taft 值、Gutman 规定的供体和受体数之间存在令人满意的相关性(R = 0.795-0.993)。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
自引率
0.00%
发文量
0
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信