A simple structural hydrazide-based gelator as a fluoride ion colorimetric sensor

Abstract

A 4-nitrobenzohydrazide derivative, N-(3,4,5-octyloxybenzoyl)-N′-(4′-nitrobenzoyl)hydrazine (C8), was synthesized. It could form stable gels in some of the tested organic solvents. The wide-angle X-ray diffraction analysis showed that the xerogels exhibited a layered structure. SEM images revealed that the molecules self-assembled into fibrous aggregates in the xerogels. FT-IR studies confirmed that the intermolecular hydrogen bonding between CO and N–H groups was the major driving force for the formation of self-assembling gel processes. The gel is utilized for a ‘naked eye’ detection of fluoride ions, through a reversible gel–sol transition, which is associated with a color change from colorless to red. An extended conjugated system formed through the phenyl group and a five-membered ring based on intramolecular hydrogen bonding between the oxygen atom near the deprotonation nitrogen atom and the other NH, which is responsible for the dramatic color change upon addition of fluoride ions.