I. O. Gudkova, E. A. Sorokina, E. A. Zaborin, M. S. Polinskaya, O. V. Borshchev, S. A. Ponomarenko
{"title":"Peculiar Features of the Reduction of Keto Group in the Synthesis of Mono- and Dialkyl-Substituted Benzo[b]benzo[4,5]thieno[2,3-d]thiophene","authors":"I. O. Gudkova, E. A. Sorokina, E. A. Zaborin, M. S. Polinskaya, O. V. Borshchev, S. A. Ponomarenko","doi":"10.1134/s1070428024060137","DOIUrl":null,"url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>Mono- and dioctyl-substituted benzo[<i>b</i>]benzo[4,5]thieno[2,3-<i>d</i>]thiophenes <b>C8-BTBT</b> and <b>C8-BTBT-C8</b> that are widely used as organic semiconductors in the manufacture of various organic electronic devices have been synthesized in two steps, by Friedel–Crafts acylation of benzo[<i>b</i>]benzo[4,5]thieno[2,3-<i>d</i>]thiophene (BTBT) and subsequent reduction of the ketone group(s). Taking into account that the limiting stage in the synthesis of such compounds is the reduction stage, different methods for the reduction acyl-substituted BTBT derivatives have been studied and probable reduction mechanisms have been proposed. The best results in the keto group reduction stage have been obtained with the use of hydrazine hydrate as reducing agent.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8000,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1134/s1070428024060137","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Mono- and dioctyl-substituted benzo[b]benzo[4,5]thieno[2,3-d]thiophenes C8-BTBT and C8-BTBT-C8 that are widely used as organic semiconductors in the manufacture of various organic electronic devices have been synthesized in two steps, by Friedel–Crafts acylation of benzo[b]benzo[4,5]thieno[2,3-d]thiophene (BTBT) and subsequent reduction of the ketone group(s). Taking into account that the limiting stage in the synthesis of such compounds is the reduction stage, different methods for the reduction acyl-substituted BTBT derivatives have been studied and probable reduction mechanisms have been proposed. The best results in the keto group reduction stage have been obtained with the use of hydrazine hydrate as reducing agent.
期刊介绍：
Russian Journal of Organic Chemistry is an international peer reviewed journal that covers all aspects of modern organic chemistry including organic synthesis, theoretical organic chemistry, structure and mechanism, and the application of organometallic compounds in organic synthesis.
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