Three-Component Synthesis of Cryofluorescent 2,4-Disubstituted 3H-1,5-Benzodiazepines - Conformational Control of ­Emission Properties

Autor:	Benjamin Willy, Frank Rominger, Thomas Müller, Timea Dallos, Jan Schönhaber
Rok vydání:	2008
Předmět:	C c coupling Structure analysis Component (thermodynamics) Chemistry Organic Chemistry Michael reaction Sonogashira coupling Physical and Theoretical Chemistry Absorption (chemistry) Photochemistry Fluorescence
Zdroj:	European Journal of Organic Chemistry. 2008:4796-4805
ISSN:	1099-0690 1434-193X
Popis:	2,4-Disubstituted benzodiazepines are readily synthesized in good yields from acyl chlorides, terminal alkynes, and benzene-1,2-diamines by a consecutive one-pot, three-component Sonogashira coupling/Michael addition/cyclocondensation sequence. These diazepines display intense solid-state fluorescence, but only weak emission in solution at room temperature. The absorption and emission maxima can be controlled by the substitution pattern. Upon cooling, however, the phenomenon of cryofluorescence can be observed. X-ray structure analysis and temperature-dependent NMR indicate that freezing out of conformational interconversions is the source of the thermochromicity observed upon UV excitation.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
Databáze:	OpenAIRE
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