1,3‐Thiazolium‐4‐aminides: Syntheses and Characterization of Fluorescent Mesoionic Compounds

Autor:	Mimoza Gjikaj, Jan C. Namyslo, Andreas Schmidt, Jörg Adams, Alena Therese Storm
Rok vydání:	2021
Předmět:	chemistry.chemical_compound Chemistry ddc:540 Organic Chemistry article Mesoionic Physical and Theoretical Chemistry Thiazole Fluorescence Combinatorial chemistry Characterization (materials science)
Zdroj:	European Journal of Organic Chemistry. 2021:4803-4815
ISSN:	1099-0690 1434-193X
DOI:	10.1002/ejoc.202100794
Popis:	A series of mesoionic 1,3-thiazolium-4-aminides was synthesized starting from thioamides and chloroacetonitrile via cyanomethylbenzimidothioates which were cyclized by benzoylchloride. Depending on the reaction conditions 4-amino-1,3-thiazolium salts and 4-N-benzamido-1,3-thiazolium salts were obtained (X-ray structure analysis). Substitution of the amino groups with benzoyl chloride gave a series of the title mesoionic compounds (X-ray structure analysis) which were examined spectroscopically. Negative solvatochromism was found and temperature-dependent as well as time-resolved fluorescence measurements were made. Long lifetimes of the excited states (30–50 ns) were detected. Calculated frontier orbital profiles gain insight into the characteristics of 1,3-thiazolium-4-aminides as conjugated mesomeric betaines.
Databáze:	OpenAIRE
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