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阳离子型和甜菜碱型硼化吖啶鎓染料：合成、表征及光催化活性

Cationic and Betaine-Type Boronated Acridinium Dyes: Synthesis, Characterization, and Photocatalytic Activity.

作者信息

Durka Krzysztof, Urban Mateusz, Dąbrowski Marek, Jankowski Piotr, Kliś Tomasz, Luliński Sergiusz

机构信息

Faculty of Chemistry, Department of Physical Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland.

出版信息

ACS Omega. 2019 Feb 1;4(2):2482-2492. doi: 10.1021/acsomega.8b03290. eCollection 2019 Feb 28.

DOI:10.1021/acsomega.8b03290
PMID:31459486
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6648561/
Abstract

A series of isomeric boronated acridinium dyes were obtained by reactions of 10-(4'-octyloxyphenyl) functionalized 9(10)-acridanone derivative with lithiated phenylboronic azaesters followed by aromatization with perchloric acid. The effect of the position of boronic group attached at ortho, meta, and para positions of the 9-phenyl ring on the photophysical properties was investigated. Conversion to related betaine trifluoroborato-substituted compounds was successfully performed, and the effect of this structural change on UV-vis absorption and fluorescence spectroscopy characteristics was established. Furthermore, cyclic voltammetry studies revealed that electrochemical behavior of cationic versus betaine structures is different in terms of redox potential values as well as stability. The theoretical calculations revealed a different scheme for molecular excitation processes in B(OH) versus BF -substituted compounds as charge transfer to acridinium core is observed from -aryl or -aryl moiety, respectively. Obtained compounds were active as photocatalysts in selected visible-light-promoted addition reactions to unsaturated substrates.

摘要

通过10-(4'-辛氧基苯基)官能化的9(10)-吖啶酮衍生物与锂化苯基硼酸氮杂酯反应，随后用高氯酸进行芳构化，得到了一系列异构的硼化吖啶鎓染料。研究了硼酸基团连接在9-苯环的邻位、间位和对位上的位置对光物理性质的影响。成功地将其转化为相关的甜菜碱三氟硼酸盐取代的化合物，并确定了这种结构变化对紫外可见吸收和荧光光谱特性的影响。此外，循环伏安法研究表明，阳离子结构与甜菜碱结构的电化学行为在氧化还原电位值和稳定性方面存在差异。理论计算揭示了B(OH)取代与BF取代化合物中分子激发过程的不同方案，因为分别从-芳基或-芳基部分观察到电荷转移到吖啶鎓核心。所得到的化合物在选定的可见光促进的不饱和底物加成反应中作为光催化剂具有活性。

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