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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
Abstrakt
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.
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Autorzy (6)
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Beata Zadykowicz
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Artur Sikorski
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Tadeusz Połoński prof. dr hab. inż.
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Katarzyna Eichstaedt
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Pełna treść
- Wersja publikacji
- Accepted albo Published Version
- Licencja
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Informacje szczegółowe
- Kategoria:
- Publikacja w czasopiśmie
- Typ:
- artykuły w czasopismach
- Opublikowano w:
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Materials
nr 13,
ISSN: 1996-1944 - Język:
- angielski
- Rok wydania:
- 2020
- Opis bibliograficzny:
- Alfuth J., Zadykowicz B., Sikorski A., Połoński T., Eichstaedt K., Olszewska T.: 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// Materials -Vol. 13,iss. 21 (2020), s.4908-
- DOI:
- Cyfrowy identyfikator dokumentu elektronicznego (otwiera się w nowej karcie) 10.3390/ma13214908
- Źródła finansowania:
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- Program Supporting Open Access (uzupełnienie funduszu Publikacje 2020 wprowadzonego pismem okólnym Rektora PG nr 38/2019 z 13 listopada 2019r.)
- Weryfikacja:
- Politechnika Gdańska
wyświetlono 101 razy