Taylor Chin, A. Phipps, F. Fronczek
2010
Citations
1
Influential Citations
5
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
4-[(E)-2-(4-Carboxyphenyl)diazenyl]-morpholine (1) was prepared in 33% yield from a coupling reaction between morpholine and the diazonium ion formed from 4-aminobenzoic acid. X-ray structural analysis of 1 yielded two important insights into its structure: the geometry of the N―N double bond and the partial delocalization across the linear triazene moiety. The absorption spectra of 1 in dilute acetonitrile and 2-methyltetrahydrofuran solutions both featured an intense (e ≈ 20,000 M−1cm−1) band centered at 320–324 nm that was assigned as a mixture of π π* and n π* transitions. Emission was observed at 383 and 379 nm from dilute acetonitrile and 2-methyltetrahydrofuran solutions of 1, respectively, with the latter being red-shifted to 439 nm at 77 K. Emission lifetime data for compound 1 provided evidence that the emission was a mixture of two excited state transitions.