Organogelators derived from the bisphenol A scaffold

Bisphenol A, a common precursor molecule used in the preparation of some polymers, was investigated as a possible scaffold for the design and synthesis of small-molecule gelators. To this end, a small library of ten molecules was synthesized by appending different n-alkyl chains and aromatic moieties via the p-hydroxyl groups in a single step. Five of these served as excellent gelators of several polar solvents. All the gelators contained n-alkyl chains, while none of the aromatic moieties imparted the gelling ability to the molecules. The minimum gelation concentrations ranged between 1-3%, with the ether-linked gelators more efficient than the ester-linked ones. The gel-to-sol transition temperatures observed for these gels were in the range of 26-54 degrees C. Detailed characterizations of the gels for two representative gelators were carried out using techniques like FTIR, UV-vis absorption, scanning electron microscopy, rheology, powder XRD, and contact angle measurement. The gels showed good absorption profiles for two water-soluble dyes. Based on these results, we propose that 'bisphenol A' can be conveniently exploited as a versatile core gelating scaffold in the design of many other small-molecule gelators.

Automated summary

A series of small-molecule gelators were synthesized by modifying molecules containing bisphenol A, with some showing good gelation properties. The n-alkyl chains in the gelators contributed more to the gelling ability, while aromatic moieties did not exhibit gelation effects. Detailed characterizations of the gels using various techniques demonstrated the potential application value of bisphenol A as a core gelating scaffold in designing other small-molecule gelators.