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Article Dans Une Revue Angewandte Chemie International Edition Année : 2020

Activating chalcogen bonding (ChB) in alkylseleno/ alkyltelluroacetylenes toward ChB directionality control

Résumé

Activation of a deep electron-deficient area on chalcogen atoms (Ch=Se, Te) is demonstrated in alkynyl chalcogen derivatives, in the prolongation of the (C≡)C-Ch bond. The solid-state structures of 1,4-bis(methylselenoethynyl)perfluorobenzene (1Se) show the formation of recurrent chalcogen-bonded (ChB) motifs. Association of 1Se and the tellurium analogue 1Te with 4,4'-bipyridine and with the stronger Lewis base 1,4-di(4-pyridyl)piperazine gives 1:1 co-crystals with 1D extended structures linked by short and directional ChB interactions, comparable to those observed with the corresponding halogen bond (XB) donor, 1,4-bis(iodoethynyl)-perfluorobenzene. This "alkynyl" approach for chalcogen activation provides the crystal-engineering community with efficient, and neutral ChB donors for the elaboration of supramolecular 1D (and potentially 2D or 3D) architectures, with a degree of strength and predictability comparable to that of halogen bonding in iodoacetylene derivatives.

Domaines

Chimie
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Dates et versions

hal-02959801 , version 1 (17-11-2020)

Identifiants

Citer

Arun Dhaka, Olivier Jeannin, I.-R. Jeon, Marc Fourmigué, Emmanuel Aubert, et al.. Activating chalcogen bonding (ChB) in alkylseleno/ alkyltelluroacetylenes toward ChB directionality control. Angewandte Chemie International Edition, 2020, 59 (52), pp.23583-23587. ⟨10.1002/anie.202011981⟩. ⟨hal-02959801⟩
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