Skip to Main content Skip to Navigation
Journal articles

Chalcogen bonding in crystalline diselenides and selenocyanates: From molecules of pharmaceutical interest to conducting materials

Abstract : Organic diselenides are nowadays investigated for pharmaceutical applications, as well as in material science in molecular (semi)conductors. In both application's domains, their interactions with Lewis bases, in solution or in the solid state, has been shown to play a crucial role in their biological activity or in their electronic structure. The current comprehensive survey of reported crystal structures of organic diselenides demonstrates the recurrent setting of intermolecular as well as intramolecular chalcogen bonding interactions (ChB) between the selenium atoms acting as ChB donors and Lewis bases. These interactions take place along the two covalent bonds of the selenium atom. In diselenides, stronger interactions are found in the prolongation of the Se[sbnd]Se bond than in the prolongation of the C[sbnd]Se bond. Charge activation of ChB is demonstrated in dicationic diselenides or in cation radical salts of 1,2-diselenole derivatives. This survey is extended to the structures of organic selenocyanates whose crystal structures reflect also the presence of two σ-holes, with a much stronger one in the prolongation of the NC[sbnd]Se bond. Such ChB interactions of selenocyanates with polytopic Lewis bases or with halide anions open novel strategies in crystal engineering and anion recognition strategies.
Document type :
Journal articles
Complete list of metadatas

Cited literature [118 references]  Display  Hide  Download

https://hal-univ-rennes1.archives-ouvertes.fr/hal-02400026
Contributor : Laurent Jonchère <>
Submitted on : Wednesday, December 11, 2019 - 2:44:10 PM
Last modification on : Tuesday, December 17, 2019 - 2:25:38 AM
Long-term archiving on: : Thursday, March 12, 2020 - 9:46:27 PM

File

Fourmigué et al-2019-Chalcoge...
Files produced by the author(s)

Identifiers

Citation

M. Fourmigué, A. Dhaka. Chalcogen bonding in crystalline diselenides and selenocyanates: From molecules of pharmaceutical interest to conducting materials. Coordination Chemistry Reviews, Elsevier, 2020, 403, pp.213084. ⟨10.1016/j.ccr.2019.213084⟩. ⟨hal-02400026⟩

Share

Metrics

Record views

57

Files downloads

56