Abstract: We report a three-stage scheme (1) Pbt—NH2 + CS2  (Pbt—NH)2C=S (1) (Pbt = 4-(1,3-benzothiazole-2-yl)phenyl), (2) 1 + PPh3 + I2  Pbt—N=C=N—Pbt (2), (3) 2 + Ph2PH  (Pbt—N)(Pbt—NH)CPPh2 (3) for the synthesis of a novel luminescent phosphoguanidine 3 with an unprecedentedly high yield (90 %) at the last catalyst-free stage. It is demonstrated by the density functional theory (DFT) method that high reactivi-ty of 2, leading to such an yield, is explained by a high electrostatic potential at the cen-tral carbon atom. For 3, two polymorphs 3, 3 and a solvatomorph 3THF are pre-pared. The structures of 2, 3, 3, and 3THF are determined by single-crystal XRD. The tendency of crystals of different phenylbenzothiazole derivatives to form different con-formations is explained by the computational (DFT) data indicating that the energy change of the molecule of 3 considered as a function of the torsion angle between phenyl and benzothiazole fragments does not exceed 2 kJ/mol in the –15…30 range. Photophys-ical properties of 3 and 3THF phases are studied. It is shown that these compounds exhibit photoluminescence with an emission maximum at 510 nm.

Cite: Afonin M.Y. , Konchenko S.N. , Sukhikh T.S.
Synthesis and conformational features of luminescent phosphoguanidine with a phenylbenzothiazole substituent
Journal of Structural Chemistry. 2024. V.65. N7. P.1420-1431. DOI: 10.1134/S0022476624070138 WOS Scopus РИНЦ OpenAlex

Original: Афонин М.Ю. , Конченко С.Н. , Сухих Т.С.
Синтез и конформационные особенности люминесцентного фосфогуанидина с фенилбензотиазольным заместителем
Журнал структурной химии. 2024. Т.65. №7. 129687 . DOI: 10.26902/JSC_id129687 РИНЦ OpenAlex

Dates:

Submitted:	Mar 21, 2024
Accepted:	Mar 28, 2024
Published print:	Jul 29, 2024

Identifiers:

Web of science:	WOS:001278983100003
Scopus:	2-s2.0-85199774114
Elibrary:	68537996
OpenAlex:	W4401010749

Citing: Пока нет цитирований

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