The Synthesis,X‐ray Structure Analysis,and Photophysical Characterization of 4‐[(E)‐2‐(4‐Carboxyphenyl)diazenyl]‐morpholine |
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| Authors: | Mathew Johnson Michael Galbreath Frank R Fronczek Ralph Isovitsch |
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| Institution: | 1. Department of Chemistry, Whittier College, Whittier, CA, USA;2. Universidad Autónoma de Guadalajara, School of Medicine, Jalisco, Guadalajara, Mexico;3. Department of Chemistry, Louisiana State University, Baton Rouge, LA, USA |
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| 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 (ε ≈ 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. |
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