Crystal structures of 3-halo-2-organochalcogenylbenzo[ b ]chalcogenophenes.

Autor: Luz EQ; Laboratory of Polymers and Catalysis (LaPoCa), Department of Chemistry, Federal University of Paraná-UFPR, PO Box 19061, Curitiba, PR, 81531-980, Brazil., Santana FS; Department of Chemistry, Federal University of Paraná-UFPR, PO Box 19061, Curitiba, PR, 81531-980, Brazil., Silverio GL; Laboratory of Polymers and Catalysis (LaPoCa), Department of Chemistry, Federal University of Paraná-UFPR, PO Box 19061, Curitiba, PR, 81531-980, Brazil., Tullio SCMC; Department of Biology, East Carolina University, Greenville, North Carolina, USA., Iodice B; IOTO USA - 1997N Greene Street - Greenville, NC 27834, USA., Prola LDT; Department of Chemistry and Biology, Federal University of Technology - Paraná, Rua Deputado Heitor de Alencar Furtado, 5000, 81280-340, Curitiba, Brazil., Barbosa RV; IOTO INTERNATIONAL - Rodovia Gumercindo Boza 20088 - Campo Magro - PR, 83535-000, Brazil., Rampon DS; Laboratory of Polymers and Catalysis (LaPoCa), Department of Chemistry, Federal University of Paraná-UFPR, PO Box 19061, Curitiba, PR, 81531-980, Brazil.
Jazyk: angličtina
Zdroj: Acta crystallographica. Section E, Crystallographic communications [Acta Crystallogr E Crystallogr Commun] 2022 Feb 03; Vol. 78 (Pt 3), pp. 275-281. Date of Electronic Publication: 2022 Feb 03 (Print Publication: 2022).
DOI: 10.1107/S2056989022000962
Abstrakt: The structure of the title compounds 3-bromo-2-(phenyl-sulfan-yl)benzo[ b ]thiophene (C 14 H 9 BrS 2 ; 1 ), 3-iodo-2-(phenyl-sulfan-yl)benzo[ b ]thio-phene (C 14 H 9 IS 2 ; 2 ), 3-bromo-2-(phenyl-selan-yl)benzo[ b ]seleno-phene (C 14 H 9 BrSe 2 ; 3 ), and 3-iodo-2-(phenyl-selan-yl)benzo[ b ]seleno-phene (C 14 H 9 ISe 2 ; 4 ) were determined by single-crystal X-ray diffraction; all structures presented monoclinic ( P 2 1 / c ) symmetry. The phenyl group is distant from the halogen atom to minimize the steric hindrance repulsion for all structures. Moreover, the structures of 3 and 4 show an almost linear alignment of halogen-selenium-carbon atoms arising from the intra-molecular orbital inter-action between a lone pair of electrons on the halogen atom and the anti-bonding σ* Se-C orbital ( n halogen →σ* Se-C ). This inter-action leads to significant differences in the three-dimensional packing of the mol-ecules, which are assembled through π-π and C-H⋯π inter-actions. These data provide a better comprehension of the inter-molecular packing in benzo[ b ]chalcogenophenes, which is relevant for optoelectronic applications.
(© Q. Luz et al. 2022.)
Databáze: MEDLINE
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