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

Authors
  • Fourmigué, Marc
  • Dhaka, Arun
  • Jeannin, Olivier
  • Jeon, I.-R.
  • Aubert, Emmanuel
  • Espinosa, Enrique
Publication Date
Jan 01, 2020
Identifiers
DOI: 10.1002/anie.202011981
PMID: 32940957
OAI: oai:HAL:hal-02959801v1
Source
HAL-Descartes
Keywords
Language
English
License
Unknown
External links

Abstract

Activation of a deep electron-deficient area on chalcogen atoms (Ch = Se, Te) is demonstrated here 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 analog 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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