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

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...

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Bibliographic Details
Published in:High energy chemistry 2019-05, Vol.53 (3), p.211-218
Main Authors: Budyka, M. F., Potashova, N. I., Gavrishova, T. N., Fedulova, Yu. A.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Cyclobutane
Organic chemistry
Photochemistry
Photochromism
Physical Chemistry
Quantum chemistry
Quinoline
Xylene
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Summary: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.
ISSN:0018-1439
1608-3148
DOI:10.1134/S0018143919030044