Bekaert Indigo M, Siegler Maxime A, Wezenberg Sander J
Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands.
Department of Chemistry, Johns Hopkins University, 3400 North Charles Street., Baltimore, Maryland 21218, United States.
Org Lett. 2025 Apr 11;27(14):3612-3616. doi: 10.1021/acs.orglett.5c00707. Epub 2025 Mar 31.
Formylation of stiff-stilbene enables isomerization by visible instead of UV light, as is monitored by UV-vis and H NMR spectroscopy. Further, it allows dynamic covalent imine formation, which gives rise to slightly blue-shifted absorbance. As a result, the irradiation wavelength that is used to promote → isomerization for the formylated species, causes the opposite → isomerization for the imine derivative. This feature can be used to produce either isomer with the same light source under control of imine formation and hydrolysis. Single crystal X-ray analysis and TD-DFT calculations provide structural and electronic insight.
刚性二苯乙烯的甲酰化使得其能够通过可见光而非紫外光进行异构化，这通过紫外可见光谱和核磁共振氢谱进行监测。此外，它还能形成动态共价亚胺，导致吸光度略有蓝移。因此，用于促进甲酰化物种的顺反异构化的照射波长，会导致亚胺衍生物发生相反的顺反异构化。在亚胺形成和水解的控制下，利用同一光源，这一特性可用于制备任意一种异构体。单晶X射线分析和含时密度泛函理论计算提供了结构和电子方面的见解。
