Reported herein is the synthesis, characterization, and dye removal applications of a highly solvent-selective organogel, formed from compound (Fig. 1), a structure consisting of a 1,8-naphthalmide moiety, flexible achiral amino acid (Acp = ε-aminocaproic acid) chain, and benzene ring. Of note, structural isomer, which contains the same structural elements in a different molecular arrangement, did not form organogels under any investigated conditions, leading to insights into how structural features of the amides dictate gel formation behavior. Moreover, compound displayed remarkable solvent selectivity, with gel formation occurring only in the presence of alkylated aromatic solvents via sonication. Scanning electron microscopy (SEM) and other experimental characterization of the amide <b>1</b>-derived gel reveals the sonication-induced microfibrillar morphology, and a variety of crystalline, non-gel forming morphologies that are formed from the sonication of compound. Finally, the ability of the gel to act as a reusable material for the efficient removal of cationic organic dyes from contaminated aqueous environments is also reported, with up to 11 repeated uses of the gel still maintaining the ability to effectively remove Rhodamine B.

Sonication-induced, solvent-selective gelation of a 1,8-napthalimide-conjugated amide: Structural insights and pollutant removal applications

ACS Fall 2021

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