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The synthesis, X-ray structure analysis, and photophysical characterization of 4-[(E)-2-(4-cyanophenyl)diazenyl]-morpholine

โœ Scribed by Taylor Chin; Ashley Phipps; Frank R. Fronczek; Ralph Isovitsch

Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
110 KB
Volume
48
Category
Article
ISSN
0022-152X

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โœฆ Synopsis

Abstract

A novel triazene, 4โ€[(E)โ€2โ€(4โ€cyanophenyl)diazenyl]โ€morpholine (1) was prepared via a diazonium ion coupling reaction between 4โ€aminobenzonitrile and morpholine. The xโ€ray structure of 1 was determined and evidenced ฯ€ delocalization in the triazene subunit. The room temperature absorption spectrum of 1 in acetonitrile was dominated by an intense triazeneโ€centered ฯ€โ†’ฯ€* transition at 325 nm. Compound 1 was observed to be luminescent, with an emission maximum at 434 nm in room temperature acetonitrile solution. The emission spectrum of 1 in propionitrile glass at 77K exhibited a narrowed emission band with a maximum at 449 nm. Broad emission from 400โ€“700 nm with poorly resolved vibrational structure was observed from solid 1 at room temperature. J. Heterocyclic Chem., 2011.

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