[2+2] Photocycloaddition in a bichromophoric dyad: photochemical concerted forward reaction following Woodward-Hoffmann rules and photoinduced stepwise reverse reaction of the ring opening predissociation.

A novel biphotochromic dyad with styrylbenzo[]quinoline photochromes was designed and synthesized to study the [2+2] photocycloaddition (PCA) reaction leading to cyclobutane with two benzo[]quinoline (BQ) substituents and the reverse four-membered ring opening reaction. In the dyad, PCA occurs in a concerted manner according to the Woodward-Hoffmann rules in the ππ* excited state after excitation of the whole conjugated π-system comprising the ethylene group. Nanosecond time-resolved emission spectroscopy indicated formation of an excimer as a possible intermediate of the PCA reaction.

Emissive and reactive excimers in a covalently-linked supramolecular multi-chromophoric system with a balanced rigid-flexible structure.

A novel multi-chromophoric system, triad, in which two styrylbenzoquinoline (SBQ) photochromes are connected by a balanced rigid-flexible linker comprising 2,3-naphthylene framework (a residue of 3-oxy-2-naphthoic acid) and tetramethylene groups, was designed and synthesized to study an excimer formation in the excited state. The H NMR data testified that triad exists in solution as folded conformers with asymmetric parallel-displaced SBQ units. Under light irradiation, in the triad, competitive photoisomerization and [2 + 2] photocycloaddition reactions were observed, both reactions being reversible.