Synthesis of 7-(diethylamino)-chromene-fused quinolines and 7-(diethylamino)-4-amino-3-formyl-coumarin derivatives, structural elucidation, and photophysical properties
Document Type
Article
Publication Date
1-1-2026
Abstract
A series of 7-(diethylamino)-coumarin-based heterocycles have been designed and synthesized through the reaction of 7-diethylamino-4-chloro-3-formylcoumarins with arylamines by a one-pot acid-catalysed synthesis. By tuning the reaction time and temperature, this reaction provides a pathway to either fused coumarin–quinoline scaffolds (3, 4meta, 4para, 6, and 7) or unfused 7-diethylamino-4-amino-3-formyl-coumarins (8–12), all in moderate to good yields (58–87%). The fused derivatives (3–7) display unusual photophysical behavior in a wide range of solvents, whereas the unfused systems (8–12) are essentially non-emissive. The photophysical studies of fluorophores 3–7 exhibit dual absorption bands centered around 350 nm and 420 nm, while the emission shows pronounced solvent dependence, with high fluorescence efficiency (Φ = 0.62–0.82) and large Stokes shifts (>2000 cm−1). All compounds are fully characterized, and X-ray quality crystals of compounds 4para and 9ortho are also reported.
Publication Title
Organic and Biomolecular Chemistry
Recommended Citation
Hosen, N.,
Case, L.,
Dukette, S.,
Pokhrel, N.,
Wallace, K.
(2026). Synthesis of 7-(diethylamino)-chromene-fused quinolines and 7-(diethylamino)-4-amino-3-formyl-coumarin derivatives, structural elucidation, and photophysical properties. Organic and Biomolecular Chemistry.
Available at: https://aquila.usm.edu/fac_pubs/22140
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