Pylova Ekaterina, Lasorne Benjamin, McClenaghan Nathan D, Jonusauskas Gediminas, Taillefer Marc, Konchenko Sergey N, Prieto Alexis, Jaroschik Florian
ICGM, Univ Montpellier, CNRS, ENSCM, 34090, Montpellier, France.
Nikolaev Institute of Inorganic Chemistry SB RAS, Prosp. Lavrentieva 3, 630090, Novosibirsk, Russia.
Chemistry. 2024 Dec 5;30(68):e202401851. doi: 10.1002/chem.202401851. Epub 2024 Nov 14.
We have studied 2-(2-aminophenyl)benzothiazole and related derivatives for their photophysical properties in view of employing them as new and readily tunable organic photocatalysts. Their triplet energies were estimated by DFT calculations to be in the range of 52-57 kcal mol, suggesting their suitability for the [2+2] photocycloaddition of unsaturated acyl imidazoles with styrene derivatives. Experimental studies have shown that 2-(2-aminophenyl)benzothiazoles comprising alkylamino groups (NHMe, NHPr) or the native amino group provide the best photocatalytic results in these visible-light mediated [2+2] reactions without the need of any additives, yielding a range of cyclobutane derivatives. A combined experimental and theoretical approach has provided insights into the underlying triplet-triplet energy transfer process.
鉴于将2-(2-氨基苯基)苯并噻唑及其相关衍生物用作新型且易于调节的有机光催化剂，我们对其光物理性质进行了研究。通过密度泛函理论（DFT）计算估计，它们的三线态能量在52-57千卡/摩尔范围内，这表明它们适用于不饱和酰基咪唑与苯乙烯衍生物的[2+2]光环加成反应。实验研究表明，含有烷基氨基（NHMe、NHPr）或天然氨基的2-(2-氨基苯基)苯并噻唑在这些可见光介导的[2+2]反应中能提供最佳的光催化效果，无需任何添加剂，可生成一系列环丁烷衍生物。实验与理论相结合的方法为潜在的三线态-三线态能量转移过程提供了深入见解。
