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

Abstract

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 p delocalization in the triazene subunit. The room temperature absorption spectrum of 1 in acetonitrile was dominated by an intense triazene-centered p!p* 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.

Syntheses and crystal structure of 4-[(pyridin-3-yl)diazenyl]morpholine and 1-[(pyridin-3-yl)diazenyl]-1,2,3,4-tetrahydroquinoline

“…The N2-N3 double-bond distance of 1.2679 (13) A ånd the N1-N2 single-bond distance of 1.3501 (12) A ˚in EMUDEX are in accordance with those reported for OFUBUO (Mukai et al, 2013), EZEXEN (Gholivand et al, 2010), FUZLUI (Pye et al, 2010). The structures of HAHQOZ (Johnson et al 2016), HUHGEZ (Isovitsch & Fronczek, 2020), IJEVUR (Gangwar et al, 2021), OPAVUX (Chin et al, 2011) and RUJQIX (Chin et al, 2009) feature similar intermolecular hydrogen-bonding interactions to those in I, resulting in supramolecular networks.…”