Activating Chalcogen Bonding (ChB) in Alkylseleno/Alkyltelluroacetylenes toward Chalcogen Bonding Directionality Control |
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Authors: | Arun Dhaka Dr Olivier Jeannin Dr Ie-Rang Jeon Dr Emmanuel Aubert Prof Enrique Espinosa Dr Marc Fourmigué |
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Institution: | 1. Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) UMR 6226, 35042 Rennes, France;2. Laboratoire CRM2, UMR CNRS 7036, Institut Jean Barriol, Université de Lorraine, BP 70239, 54506 Vandoeuvre-les-Nancy, France |
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Abstract: | 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. |
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Keywords: | alkynes chalcogen bonding crystal engineering Lewis bases |
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