Article first published online: 2 SEP 2010
Copyright © 2010 HeteroCorporation
Journal of Heterocyclic Chemistry
Volume 48, Issue 1, pages 215–217, January 2011
How to Cite
Chin, T., Phipps, A., Fronczek, F. R. and Isovitsch, R. (2011), The synthesis, X-ray structure analysis, and photophysical characterization of 4-[(E)-2-(4-cyanophenyl)diazenyl]-morpholine. J. Heterocyclic Chem., 48: 215–217. doi: 10.1002/jhet.513
- Issue published online: 24 JAN 2011
- Article first published online: 2 SEP 2010
- Manuscript Received: 27 JAN 2010
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A novel triazene, 4-[(E)-2-(4-cyanophenyl)diazenyl]-morpholine (1) was prepared via a diazonium ion coupling reaction between 4-aminobenzonitrile and morpholine. The x-ray structure of 1 was determined and evidenced π delocalization in the triazene subunit. The room temperature absorption spectrum of 1 in acetonitrile was dominated by an intense triazene-centered ππ* 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 400–700 nm with poorly resolved vibrational structure was observed from solid 1 at room temperature. J. Heterocyclic Chem., 2011.