Results
Title

Activating Chalcogen Bonding (ChB) in Alkylseleno/Alkyltelluroacetylenes toward Chalcogen Bonding Directionality Control.

Authors

Dhaka, Arun; Jeannin, Olivier; Jeon, Ie‐Rang; Aubert, Emmanuel; Espinosa, Enrique; Fourmigué, Marc

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.

Subjects

LEWIS bases; TELLURIUM compounds; HEXAFLUOROBENZENE; PIPERAZINE

Publication

Angewandte Chemie, 2020, Vol 132, Issue 52, p23789

ISSN

0044-8249

Publication type

Academic Journal

DOI

10.1002/ange.202011981