Irreversible two-photon photorearrangement of 1,2-diarylethenes is a unique process providing access to complex 2a ,5a-dihydro-5,6-dithiaacenaphthylene (DDA) heterocyclic core. This reaction was serendipitously discovered during studies on photoswitchable diarylethenes and was initially considered as a highly undesired process. However, in recent years, it has been recognized as an efficient photochemical reaction, interesting by itself and as a promising synthetic method for the synthesis of challenging molecules. Herein, we discuss the state-of-the-art in studies on this notable process.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1002/chem.202301480 | DOI Listing |
Chemistry
October 2023
Department of Chemistry and Pharmacy, Friedrich-Alexander University Erlangen-Nürnberg (FAU), Egerlandstrasse 1, 91058, Erlangen, Germany.
Irreversible two-photon photorearrangement of 1,2-diarylethenes is a unique process providing access to complex 2a ,5a-dihydro-5,6-dithiaacenaphthylene (DDA) heterocyclic core. This reaction was serendipitously discovered during studies on photoswitchable diarylethenes and was initially considered as a highly undesired process. However, in recent years, it has been recognized as an efficient photochemical reaction, interesting by itself and as a promising synthetic method for the synthesis of challenging molecules.
View Article and Find Full Text PDFPhys Chem Chem Phys
March 2020
Novosibirsk State University, 2 Pirogova Str., 630090, Novosibirsk, Russian Federation.
A mechanistic study of the photochromic properties and photodegradation processes of an asymmetrical diarylcyclopentenone bearing thiophene and benzothiophene units using stationary photolysis, nanosecond laser flash photolysis and time-resolved luminescence was performed. It was found that the light-induced reversible isomerization of (3-(2,5-dimethyltiophen-3-il)-2-(2-methyl-1-benzylthiophen-3-il)cyclopent-2-en-1-one, compound 1) from open to closed form is a common photochromic transformation inherent to diarylethenes, while the photodegradation process proceeds in two ways. The first is a formal 1,2-dyotropic rearrangement, proceeding without the participation of oxygen.
View Article and Find Full Text PDFJ Am Chem Soc
August 2003
Departamento de Química Orgánica, Facultad de Química, Universidad Complutense, 28040-Madrid, Spain.
1,2-Dyotropic rearrangement can be induced by irradiation of properly functionalized Fischer carbenes. This novel reaction takes place by a stepwise mechanism and with double inversion of configuration at the static scaffold. Good yields are obtained with both cyclic and acyclic structures, thus suggesting that this unprecedented transformation can be extended to other organometallic systems.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!