期刊论文详细信息
Materials 卷:13
Effect of Aromatic System Expansion on Crystal Structures of 1,2,5-Thia- and 1,2,5-Selenadiazoles and Their Quaternary Salts: Synthesis, Structure, and Spectroscopic Properties
Tadeusz Połoński1  Teresa Olszewska1  Jan Alfuth1  Katarzyna Eichstaedt1  Artur Sikorski2  Beata Zadykowicz3 
[1] Department of Organic Chemistry, Gdańsk University of Technology, 80-233 Gdańsk, Poland;
[2] Laboratory of Crystallochemistry, Faculty of Chemistry, University of Gdańsk, 80-308 Gdańsk, Poland;
[3] Luminescence Research Group, Faculty of Chemistry, University of Gdańsk, 80-308 Gdańsk, Poland;
关键词: chalcogenadiazoles;    chalcogen bonds;    crystal engineering;    spectral properties;   
DOI  :  10.3390/ma13214908
来源: DOAJ
【 摘 要 】

Rational manipulation of secondary bonding interactions is a crucial factor in the construction of new chalcogenadiazole-based materials. This article reports detailed experimental studies on phenanthro[9,10-c][1,2,5]chalcogenadiazolium and 2,1,3-benzochalcogenadiazolium salts and their precursors. The compounds were synthesized, characterized employing NMR and UV-Vis spectroscopy. TD-DFT calculations were also performed. The influence of the size of the aromatic system on the molecular motifs formed by the compounds in the solid state has been studied by means of single-crystal X-ray diffraction. In case of the salts, the nature of an anion was also taken into consideration. The results show that cyclic [E···N]2 supramolecular synthon connects neighboring molecules of phenanthro[9,10-c][1,2,5]chalcogenadiazoles, with a relatively large aromatic system, in dimers regardless of the chalcogen atom in the molecule. Both N-methyl-2,1,3-benzothiadiazolium and N-methylphenanthro[9,10-c][1,2,5]chalcogenadiazolium cations have a strong affinity for triflate and iodide anions, therefore the formation of S···N or Se···N secondary bonding interactions is observed only in two out of the eight quaternary salts. Less coordinating anions must be used to enable the building blocks studied to form cyclic [E···N]2 synthons. Moreover, for two of the triflate salts, which are isostructural, a new supramolecular motif has been observed.

【 授权许可】

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