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Buchwald–Hartwig Amination of Aryl Halides with Heterocyclic Amines in the Synthesis of Highly Fluorescent Benzodifuran-Based Star-Shaped Organic Semiconductors
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-12-03 , DOI: 10.1021/acs.joc.1c01583 Mariusz J Bosiak 1, 2 , Alicja A Zielińska 2, 3 , Piotr Trzaska 1, 2 , Dariusz Kędziera 4 , Jörg Adams 5
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-12-03 , DOI: 10.1021/acs.joc.1c01583 Mariusz J Bosiak 1, 2 , Alicja A Zielińska 2, 3 , Piotr Trzaska 1, 2 , Dariusz Kędziera 4 , Jörg Adams 5
Affiliation
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The study of palladium-catalyzed amination of bromobenzene with aromatic and heterocyclic amines, widely used in the synthesis of organic semiconductors, was performed. The best conditions for the coupling of aryl bromides with carbazole, diphenylamine, phenoxazine, phenothiazine, 9,9-dimethyl-9,10-dihydroacridine, and their derivatives have been developed. Based on the results, nine new star-shaped organic semiconductors, exhibiting up to 100% fluorescent quantum yield in the 400–550 nm range, have been synthesized in good yields. The TDDFT calculations of the absorption spectra revealed a good correlation with experimental results and slight solvatochromic effects with a change in the polarity of the solvent.
中文翻译：
Buchwald-Hartwig 芳基卤化物与杂环胺在合成高荧光苯并二呋喃基星形有机半导体中的胺化
研究了钯催化溴苯与芳香胺和杂环胺的胺化，广泛用于有机半导体的合成。已开发出芳基溴化物与咔唑、二苯胺、吩恶嗪、吩噻嗪、9,9-二甲基-9,10-二氢吖啶及其衍生物偶联的最佳条件。基于这些结果，已经以良好的产率合成了九种新的星形有机半导体，在 400-550 nm 范围内表现出高达 100% 的荧光量子产率。吸收光谱的 TDDFT 计算揭示了与实验结果的良好相关性以及随着溶剂极性变化的轻微溶剂化变色效应。
更新日期：2021-12-17
中文翻译：
Buchwald-Hartwig 芳基卤化物与杂环胺在合成高荧光苯并二呋喃基星形有机半导体中的胺化
研究了钯催化溴苯与芳香胺和杂环胺的胺化，广泛用于有机半导体的合成。已开发出芳基溴化物与咔唑、二苯胺、吩恶嗪、吩噻嗪、9,9-二甲基-9,10-二氢吖啶及其衍生物偶联的最佳条件。基于这些结果，已经以良好的产率合成了九种新的星形有机半导体，在 400-550 nm 范围内表现出高达 100% 的荧光量子产率。吸收光谱的 TDDFT 计算揭示了与实验结果的良好相关性以及随着溶剂极性变化的轻微溶剂化变色效应。
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