Sonication-Induced, Solvent-Selective Gelation of a 1,8-Napthalimide-Conjugated Amide: Structural Insights and Pollutant Removal Applications

Abstract

Reported herein is the synthesis, characterization, and dye removal applications of a highly solvent-selective organogel-forming amide, compound 1, which contains a 1,8-naphthalmide moiety, flexible n-hexyl chain, and benzene ring. This compound displayed remarkable solvent selectivity, with gel formation occurring only in the presence of alkylated aromatic solvents. Detailed structural characterization of the gels, combined with notable theoretical insights, is invoked to explain the highly selective gelation properties of compound 1, as is a comparison to non-gel forming structural isomer 2, which contains the same structural elements in a different arrangement. Finally, the ability of the gel derived from compound 1 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.

Peptide‐Bridged Naphthalimide–Dithienylethene Dyad with Aggregation‐Induced‐Emission Activity: Application in Forensic Fingerprint Technology

“…In case of 6 , gelation was not occurred may be due to the imbalance of hydrophobicity and hydrophilicity of short alkyl chain in the medium. On contrary, compound 7 with longer and flexible eight‐carbon alkyl chain fulfilled the balanced condition to form gel [54] . The photoisomerization process was also investigated in gel state where the reversible color change from pale yellow ( 7 o ) to purple ( 7c ) was observed upon consecutive irradiation of UV light (254 nm) and visible light (>450 nm) (Figure 7b).…”

“…On contrary, compound 7 with longer and flexible eight-carbon alkyl chain fulfilled the balanced condition to form gel. [54] The photoisomerization process was also investigated in gel state where the reversible color change from pale yellow (7 o) to purple (7c) was observed upon consecutive irradiation of UV light (254 nm) and visible light (> 450 nm) (Figure 7b). Further, to characterize the gelation behavior, sample at same concentration (6 mg/mL) was prepared and the rheological experiment was performed.…”

Cyanide Recognition and Phase‐Selective Removal of Toxic Cationic Dyes from Water Using a New Naphthalimide‐coupled Poly (aryl ether) Gelator

“…While the poly aryl ether segment in the design can influence aggregation, naphthalimide, due to its broad, flat aromatic structure, may participate in π‐π stacking interactions, allowing solvents to be trapped within the ordered structure [12a,16] . Moreover, naphthalimide shows tunable fluorescence emission for which the monitoring of aggregation and sensing of analytes can easily be done.…”

“…[11] Of the different applications, removal of toxic dyes as pollutants by supramolecular gels draws attention. [12] Toxic dyes which are directly discharged into the aqueous environment for human activities threat the environment and human health. To protect the water quality, efficient removal of the dyes from polluted water is essential.…”

Polymorphs, ionic cocrystal and inclusion complex of N-amino-1,8-naphthalimide

“…The information on self-assemblies with enhanced composition becomes important on applications in materials, or for recovery from solution where they may remain as vulnerable contaminants. 31 Appropriately functionalized acid or base derivatives form salts or ionic cocrystals [32][33][34][35][36][37] or stabilize zwitterion forms. 38 The stacking effect and the concomitant hydrogen bond donor/acceptor behavior of naphthalimide derivatives make them attractive to generate polymorphs.…”