The research on the photochemistry of diarylethenes is continued in the Zelinsky Institute

In recent decades, the photochemistry of diarylethenes and their derivatives has been actively developing. One of the areas of development of this area is highly effective photoswitches with improved working characteristics for the creation of intellectual materials. Another promising direction is the study of irreversible photocyclizations of diaryletenes. These studies include analysis of the mechanistic aspects of these processes, as well as the development of effective methods for the synthesis of polyaromatic compounds from diarylethenes.

Scientists of the Laboratory of Heterocyclic Compounds of the ZIOC over the past years have been actively engaged in various directions in the chemistry of diarylethenes. In one of their last works, they studied skeletal photorearrangement with the participation of a UV-induced 6π-electrocyclization of diarylethenes with various “ethene bridges”. It was found that among the three possible ways of reaction after 6π-electrocyclization, such as radical abstraction, sigmatropic shift or deprotonation, it is the last option that is predominant. The introduction of an electron-withdrawing substituent into the “ethene bridge” of diarylethenes and/or the use of tertiary amines as a proton acceptor favors the deprotonation process. Experimental results are well consistent with theoretical calculations with the method of density functional theory.
 

Source:

A. V. Zakharov, S. M. Timofeeva, A. V. Yadykov, M. M. Krayushkin, V. Z. Shirinian Skeletal photoinduced rearrangement of diarylethenes: ethene bridge effects // Org. Biomol. Chem., 2023, 21, 2015-2023. DOI: 10.1039/d2ob02315f.