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Cationic and Betaine-Type Boronated Acridinium Dyes: Synthesis, Characterization, and Photocatalytic Activity
ACS Omega ( IF 3.7 ) Pub Date : 2019-02-01 00:00:00 , DOI: 10.1021/acsomega.8b03290 Krzysztof Durka 1 , Mateusz Urban 1 , Marek Dąbrowski 1 , Piotr Jankowski 1 , Tomasz Kliś 1 , Sergiusz Luliński 1
ACS Omega ( IF 3.7 ) Pub Date : 2019-02-01 00:00:00 , DOI: 10.1021/acsomega.8b03290 Krzysztof Durka 1 , Mateusz Urban 1 , Marek Dąbrowski 1 , Piotr Jankowski 1 , Tomasz Kliś 1 , Sergiusz Luliński 1
Affiliation
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A series of isomeric boronated acridinium dyes were obtained by reactions of 10-(4′-octyloxyphenyl) functionalized 9(10H)-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)2 versus BF3–-substituted compounds as charge transfer to acridinium core is observed from N-aryl or B-aryl moiety, respectively. Obtained compounds were active as photocatalysts in selected visible-light-promoted addition reactions to unsaturated substrates.
中文翻译：
阳离子和甜菜碱型硼化A啶染料：合成，表征和光催化活性。
通过10-（4'-辛基氧苯基）官能化的9（10 H）-ac啶酮衍生物与锂化的苯基硼氮杂酯，然后用高氯酸进行芳构化。研究了在9-苯环的邻，间和对位上连接的硼基的位置对光物理性质的影响。成功地进行了相关甜菜碱三氟硼酸酯取代化合物的转化，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势值和稳定性方面是不同的。理论计算揭示了在B（OH）2与BF 3 –中分子激发过程的不同方案。分别从N-芳基或B-芳基部分观察到取代基化合物作为电荷转移到transfer啶核上。所获得的化合物在选择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。
更新日期：2019-02-01
中文翻译：
阳离子和甜菜碱型硼化A啶染料：合成，表征和光催化活性。
通过10-（4'-辛基氧苯基）官能化的9（10 H）-ac啶酮衍生物与锂化的苯基硼氮杂酯，然后用高氯酸进行芳构化。研究了在9-苯环的邻，间和对位上连接的硼基的位置对光物理性质的影响。成功地进行了相关甜菜碱三氟硼酸酯取代化合物的转化，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势值和稳定性方面是不同的。理论计算揭示了在B（OH）2与BF 3 –中分子激发过程的不同方案。分别从N-芳基或B-芳基部分观察到取代基化合物作为电荷转移到transfer啶核上。所获得的化合物在选择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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