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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