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探索基于半花菁衍生物的有机光敏剂：一种制备酰胺键的可持续方法。

Exploring organic photosensitizers based on hemicyanine derivatives: a sustainable approach for preparation of amide linkages.

作者信息

Deol Harnimarta, Kumar Manoj, Bhalla Vandana

机构信息

Department of Chemistry, UGC Sponsored Centre for Advanced Studies-II, Guru Nanak Dev University Amritsar 143005 Punjab India

出版信息

RSC Adv. 2018 Sep 5;8(54):31237-31245. doi: 10.1039/c8ra06232c. eCollection 2018 Aug 30.

DOI:10.1039/c8ra06232c
PMID:35548727
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9085617/
Abstract

Hemicyanine derivatives C1-C4 have been synthesized and show strong absorption in the visible region, good water solubility, efficient intersystem crossing, a high singlet oxygen quantum yield and high ability to transport electrons from the donor to acceptor. These hemicyanine derivatives were utilized as photocatalysts in additive/base free oxidative amidation of aromatic aldehydes in mixed aqueous media under visible light irradiation at low catalytic loading. The hemicyanine derivative C4 exhibited recyclability upto four cycles and reusability upto five cycles in oxidative amidation of aromatic aldehydes. Among all the hemicyanine derivatives, C4 shows a high photocatalytic efficiency due to a high singlet oxygen quantum yield. All the mechanism investigations showed involvement of reactive oxygen species generated by the organic triplet photosensitizer based on hemicyanine derivative for carrying out oxidative amidation of aldehyde. Our results will encourage the design of new "metal free" organic photosensitizers and their application in photocatalysis.

摘要

半菁衍生物C1 - C4已被合成，它们在可见光区域表现出强烈吸收、良好的水溶性、高效的系间窜越、较高的单线态氧量子产率以及从供体到受体的高电子传输能力。这些半菁衍生物在低催化负载量下，于可见光照射的混合水介质中，被用作芳族醛的无添加剂/碱氧化酰胺化反应的光催化剂。半菁衍生物C4在芳族醛的氧化酰胺化反应中展现出高达四个循环的可回收性和高达五个循环的可重复使用性。在所有半菁衍生物中，C4由于具有较高的单线态氧量子产率而表现出高光催化效率。所有的机理研究表明，基于半菁衍生物的有机三重态光敏剂产生的活性氧参与了醛的氧化酰胺化反应。我们的结果将推动新型“无金属”有机光敏剂的设计及其在光催化中的应用。

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