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JOURNALS // Mendeleev Communications // Archive

Mendeleev Commun., 2024 Volume 34, Issue 1, Pages 107–109 (Mi mendc57)

This article is cited in 1 paper

Communications

Synthesis and photophysical activity of 6-substituted isocoumarins

E. S. Fedinaab, M. A. Arsenova, K. L. Isakovskayaa, D. V. Muratova, D. A. Loginovac

a A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
b Sirius University of Science and Technology, Sochi, Russian Federation
c G.V. Plekhanov Russian University of Economics, Moscow, Russian Federation

Abstract: 6-Substituted isocoumarins with aryl, alkynyl, and diphenyl-amino substituents were synthesized from 4-bromobenzoic acid by annulation with tolane via rhodium-catalyzed C–H activation followed by palladium-catalyzed cross-coupling reactions. The compounds obtained exhibit luminescence emission in the violet–blue region (370–480 nm) with quantum yields up to 95% (for the diphenylamino derivative). Aggregation of biphenyl-substituted isocoumarin leads to a strong bathochromic shift (by 80 nm) of emission as a result of intermolecular π–π stacking interactions.

Keywords: C–H annulation, cross-coupling, isocoumarins, luminescence, homogeneous catalysis.

Language: English

DOI: 10.1016/j.mencom.2024.01.032



© Steklov Math. Inst. of RAS, 2025