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

Identifieur interne : 000510 ( Main/Exploration ); précédent : 000509; suivant : 000511

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

Auteurs : Benjamin Willy ; Timea Dallos [Roumanie] ; Frank Rominger [Allemagne] ; Jan Schönhaber ; Thomas J. J. Müller [Allemagne]

Source :

RBID : ISTEX:720793BE12CE9BC09BDCA51CB1809D68A997C233

English descriptors

Abstract

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)

Url:
DOI: 10.1002/ejoc.200800619


Affiliations:


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Le document en format XML

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<div type="abstract" xml:lang="en">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)</div>
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