Deep Eutectic Solvent (DES)-Mediated One-Pot Multicomponent Green Approach for Naphthalimide-Centered Acridine-1,8-dione Derivatives and Their Photophysical Properties

Abstract

An efficient and green methodology to assemble various functionalized naphthalimide-centered acridine-1,8-dione derivatives involving a one-pot multicomponent protocol has successfully been developed. Herein, a variety of aromatic aldehydes, 1,3-diketones, 1,8naphthanoic anhydride, and hydrazine hydrate have been condensed under a reusable, inexpensive, and biodegradable deep eutectic solvent (DES) of N,N′-dimethyl urea and L-(+)-tartaric acid to obtain the desired targets under operationally mild reaction conditions with outstanding conversions. Strikingly, in this strategy, the DES plays a dual role of a catalyst and solvent and was recycled efficiently in four consecutive runs with no substantial drop in the yield of the desired product. Interestingly, the easy recovery and high reusability of the DES make this simple yet efficient protocol environmentally desirable. Moreover, the preliminary photophysical properties of thus-prepared valuable molecules have also been investigated by ultraviolet− visible (UV−vis) and fluorescence spectroscopy.

A Facile Deep Eutectic Solvent (DES) Mediated Green Approach for the Synthesis of Fluorescein and Phenolphthalein Dyes

“…Keeping the astonishing assets of DESs in consideration, and also as our central goal to construct diverse organic as well as supramolecular scaffolds under green conditions, [64–70] here we have successfully developed a novel green protocol to assemble two important dyes, fluorescein and phenolphthalein from commercially available phthalic anhydride and resorcinol/phenol using a DES of ChCl/ZnCl 2 (1 : 2). As far as our knowledge is concerned, this is the first‐ever method for the preparation of fluorescein and phenolphthalein dye molecules under green conditions involving DESs.…”

“…[43][44][45][46][47][48][49][50][51] This may be because these versatile DESs besides displaying double/triple role (e. g. solvent, catalyst, and/or reactant), also possesses stimulating features viz biodegradable, inexpensive, renewable, bio-compatible, thermally stable, inflammable, and atom economical, etc. [52][53][54][55][56][57][58][59][60][61][62][63] Keeping the astonishing assets of DESs in consideration, and also as our central goal to construct diverse organic as well as supramolecular scaffolds under green conditions, [64][65][66][67][68][69][70] here we have successfully developed a novel green protocol to assemble two important dyes, fluorescein and phenolphthalein from commercially available phthalic anhydride and resorcinol/ phenol using a DES of ChCl/ZnCl 2 (1 : 2). As far as our knowledge is concerned, this is the first-ever method for the preparation of fluorescein and phenolphthalein dye molecules under green conditions involving DESs.…”