Reversible [2+2] Photocycloaddition in Supramolecular Covalently Bound Dyad with 3-(4-Oxystyryl)benzo[f]quinoline as Photochrome and o-Xylene Bridge Group


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Abstract

Reaction of [2+2] photocycloaddition has been observed in the covalently bound bichromophoric dyad, in which the styrylbenzoquinoline (CBQ) photochromes are linked by the o-xylylene bridge group. Cyclobutane CB4M with two identical vicinal benzoquinoline (BQ) substituents undergoes reversible cycle opening (retro-photocycloaddition). A comparison with structurally similar cyclobutane CB4N, which bears the same BQ substituents linked by another bridge group and does not enter into the retro-photocycloaddition, shows that the photochemical properties can be controlled by varying the bridge group. Quantum-chemical calculations in the DFT approximation predict the existence of conformers with π-stacking interactions of SBQ photochromes in the dyad and BQ substituents in cyclobutane.

About the authors

M. F. Budyka

Institute of Problems of Chemical Physics, Russian Academy of Sciences

Author for correspondence.
Email: budyka@icp.ac.ru
Russian Federation, Chernogolovka, Moscow oblast, 142432

N. I. Potashova

Institute of Problems of Chemical Physics, Russian Academy of Sciences

Email: budyka@icp.ac.ru
Russian Federation, Chernogolovka, Moscow oblast, 142432

T. N. Gavrishova

Institute of Problems of Chemical Physics, Russian Academy of Sciences

Email: budyka@icp.ac.ru
Russian Federation, Chernogolovka, Moscow oblast, 142432

Yu. A. Fedulova

Institute of Problems of Chemical Physics, Russian Academy of Sciences; Faculty of Basic Physicochemical Engineering, Moscow State University

Email: budyka@icp.ac.ru
Russian Federation, Chernogolovka, Moscow oblast, 142432; Moscow, 119991

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