Nedeltcheva-Antonova Daniela, Antonov Liudmil
Institute of Electronics, Bulgarian Academy of Sciences, 1784 Sofia, Bulgaria.
Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, 1113 Sofia, Bulgaria.
Molecules. 2025 Apr 26;30(9):1935. doi: 10.3390/molecules30091935.
Previously, we have described a successful molecular switch (8-(benzo[d]thiazol-2-yl)quinolin-7-ol), working on the basis of long-range proton transfer. Bearing in mind that its switching efficiency in low-polarity aprotic solvents is not sufficient, in the current communication, we investigate in detail the effect of the substitution in the benzothiazole ring. By using the DFT approach, the ground-state stability of the tautomeric forms, involved in the switching process, is modeled with the aim of finding conditions where clean switching could be possible in variety of aprotic solvents. The results indicate that the substitution with electron-acceptor substituents could increase the switching efficiency, but the overall improvement depends on the positions and electronic effect of the particular substituent.
此前，我们已经描述了一种基于长程质子转移的成功分子开关（8-(苯并[d]噻唑-2-基)喹啉-7-醇）。考虑到其在低极性非质子溶剂中的开关效率不足，在本通讯中，我们详细研究了苯并噻唑环上取代基的影响。通过使用密度泛函理论（DFT）方法，对参与开关过程的互变异构体形式的基态稳定性进行建模，目的是找到在各种非质子溶剂中可能实现清晰开关的条件。结果表明，用电子受体取代基进行取代可以提高开关效率，但总体改善取决于特定取代基的位置和电子效应。
