In situ synthesis of reduction-responsive organogelators via oxidative coupling of tritylthio-terminated gallic acid derivatives

The development of low molecular‐weight gelators for the construction of stimuli‐responsive gels is increasing attention because of the great application potential. In this work, we report the design and synthesis of two new naphthalimide derivatives, GSSN and GN, as supramolecular organogelators. GSSN contains a disulfide bond in the molecule, while GN contains no disulfide bond. As a result, only GSSN exhibited reduction responsiveness. A series of tests, including UV‐vis, temperature‐dependent 1H NMR, XRD, and SEM, were carried out to characterize the gelation capability and probe into the gelation mechanism. Results showed that GN can gelate more organic solvents than GSSN. Both hydrogen bonding and π stacking contribute to the gelation. Due to the difference in the assembly of the organogelator molecules, the organogels formed by GSSN and GN presented distinct morphologies. Moreover, strong hydrophobicity was found in the organogel films of GSSN and GN, suggesting potential application as hydrophobic coating materials.

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Gallic‐Acid‐Modified Naphthalimide Containing Disulfide Bond as Reduction‐Responsive Supramolecular Organogelator

Pei

Qin

Tang

et al. 2022

ChemistrySelect

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Preparation of gallic acid-containing PCL/gelatine scaffolds as an efficient drug delivery system for growth and proliferation of human stem cells

kaaba,

Bikhof Torbati,

Majd

et al. 2024

Chem. Pap.

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Thiourea-based low molecular-mass organogelators from (+)-dehydroabietylamine

Afsar

Javed

Hashmi

et al. 2023

Journal of Sulfur Chemistry

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In situ synthesis of reduction-responsive organogelators via oxidative coupling of tritylthio-terminated gallic acid derivatives

Cited by 3 publications

References 48 publications

Gallic‐Acid‐Modified Naphthalimide Containing Disulfide Bond as Reduction‐Responsive Supramolecular Organogelator

Gallic‐Acid‐Modified Naphthalimide Containing Disulfide Bond as Reduction‐Responsive Supramolecular Organogelator

Preparation of gallic acid-containing PCL/gelatine scaffolds as an efficient drug delivery system for growth and proliferation of human stem cells

Thiourea-based low molecular-mass organogelators from (+)-dehydroabietylamine

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