Efficient one-pot three-component method for the synthesis of highly fluorescent coumarin-containing 3,5-disubstituted-2,6-dicyanoaniline derivatives under microwave irradiation

ABSTRACT

A simple and concise approach to the synthesis of coumarin-containing highly fluorescent asymmetric/symmetric 3,5-diaryl/heteroaryl-2,6-dicyanoaniline derivatives are reported. The compounds were synthesized through base catalyzed three-component one-pot synthesis reaction of 2-(1-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)ethylidene)malononitrile, aliphatic, aromatic/heteroaromatic aldehydes, and malononitrile in solvent-free reaction medium, catalyzed by piperidine under microwave irradiation method. The reaction gave the novel, highly fluorescent coumarin-containing 3,5-disubstituted-2,6-dicyanoaniline derivatives in good yields at 300 W, 80 °C in 2 min. This method provides several advantages; such as shorter reaction time, environmental friendliness, simple workup procedure, lower energy consumption and, generally, good yields with high purity. In addition, the synthesized compounds are fluorescently active dyes even in day light, except for compounds including nitro substituent, and show maximum absorption wavelengths (λ_abs.max) in the visible region in DMSO at room temperature. Thermal properties of all the synthesized compounds were also evaluated with thermal gravimetric analysis for usability as optic dye. Optical and thermal screening studies of the compounds showed that the dyes have excellent photophysical and thermal stability properties.

GRAPHICAL ABSTRACT

KEYWORDS:

• 3,5-Disubstituted-2,6-dicyanoanilines
• coumarin
• day light fluorescence
• donor–acceptor
• MWI
• one-pot synthesis

Additional information

Funding

We thank The Scientific and Technological Research Council of Turkey (TUBITAK, Project Grant No: 114Z980) for financial support.