Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 16, Pages 5665-5675Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201504328
Keywords
chalcogens; selenium; self-assembly; supramolecular chemistry; tellurium; UV; Vis spectroscopy
Categories
Funding
- Science Policy Office of the Belgian Federal Government [BELSPO-IAP 7/05]
- FNRS-FRFC [2.4.617.07.F]
- University of Namur
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The high-yielding synthesis of 2-substituted benzo-1,3-tellurazoles and benzo-1,3-selenazoles through a dehydrative cyclization reaction has been reported, giving access to a large variety of benzo-1,3-chalcogenazoles. Exceptionally, these aromatic heterocycles proved to be very stable and thus very handy to form controlled solid-state organizations in which wire-like polymeric structures are formed through secondary NY bonding interactions (SBIs) engaging the chalcogen (Y=Se or Te) and nitrogen atoms. In particular, it has been shown that the recognition properties of the chalcogen centre at the solid state could be programmed by selectively barring one of its sigma-holes through a combination of electronic and steric effects exerted by the substituent at the 2-position. As predicted by the electrostatic potential surfaces calculated by quantum chemical modelling, the pyridyl groups revealed to be the stronger chalcogen bonding acceptors, and thus the best ligand candidate for programming the molecular organization at the solid state. In contrast, the thiophenyl group is an unsuitable substituent for establishing SBIs in this molecular system as it gives rise to chalcogen-chalcogen repulsion. The weaker chalcogen donor properties of the Se analogues trigger the formation of feeble NSe contacts, which are manifested in similar solid-state polymers featuring longer nitrogen-chalcogen distances.
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