Photoinduced
charge transfer affects the efficiency and selectivity
of photochemical reactions. Incorporation of donating groups into
the isoquinolinium core allowed us to overcome the photochemical inactivity
of the corresponding dithienyl-substituted terarylenes, presumably
by redirecting the charge transfer within the molecule, and gave access
to a new family of thermally reversible photoswitches.
Irreversible two‐photon photorearrangement of 1,2‐diarylethenes is a unique process providing access to complex 2a1,5a‐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.
The photochemical 6π‐electrocyclization of diarylethenes (DAE), 2‐vinylbiaryls (VBA) and their derivatives is widely used in organic synthesis. Combination of these motifs in one molecule opens the issue of selectivity of the photochemical reaction. We have found that upon UV irradiation, 3‐(1,2‐diarylvinyl)‐2‐arylimidazo[1,2‐a]pyridines comprising both DAE and VBA moieties form products of VBA cyclization followed by oxidation. The selectivity of the process was rationalized by DFT calculations. The presented reaction gave access to highly fluorescent 5,6‐diarylnaphtho[1′,2′:4,5]imidazo[1,2‐a]pyridine derivatives.
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