Exploiting a multicomponent domino reaction strategy for the tailoring of versatile environmentally sensitive fluorophore-based nicotinonitriles incorporating pyrene and fluorene moieties.

A simplistic and highly effective protocol for the synthesis of a new class of poly-functionalized innovative nicotinonitriles incorporating pyrene and/or fluorene moieties has been developed through the domino four-component condensation reaction of 1-(pyren-1-yl)ethanone/1-(9 H -fluoren-2-yl)ethanone, numerous aromatic aldehydes, and 3-oxo-3-(pyren-1-yl)propanenitrile/3-(9 H -fluoren-2-yl)-3-oxopropanenitrile and ammonium acetate in acetic acid as a reaction medium. The advantages of this approach are the short reaction time, excellent yield, and the easy experimental workup that affords substrate diversity and operative competence under metal-free reaction conditions for the formation of C-C and C-N bonds. The substituent effects on the photophysical property-based absorption and the emission of the synthesized compounds in dichloromethane have been well-investigated. Strong absorption quenching of around 100 nm was observed when substitution of the benzene ring at the C 4 -position of the pyridine moiety occurred with an electron-donating (-N(CH 3 ) 2 ) group. All of the newly synthesized nicotinonitrile derivatives showed strong blue-green fluorescence emission with maxima in the range between 420-630 nm. These highly pronounced emission spectra will help this family of compounds to find application in many areas and the field of materials science.