Self-Assembly of Ketals of Arjunolic Acid into Vesicles and Fibers Yielding Gel-Like Dispersions

Ten aliphatic and aromatic ketals of arjunolic acid, a renewable, nanosized triterpenic acid which is obtainable from <i>Terminalia arjuna</i>, have been synthesized upon condensation with aldehydes. Self-assembly properties of the ketals have been studied in a wide range of organic liquids. With the exception of the <i>p</i>-nitrobenzylidene derivative, low concentrations of the ketals self-assemble and form gel-like dispersions in many of the organic liquids examined. The morphologies of the assemblies, studied at different distance scales by optical, electron, and atomic-force microscopies, consisted of fibrillar networks and vesicles which were able to entrap 5(6)-carboxyfluorescein as a guest molecule. X-ray diffractograms indicate that the fibrillar objects are crystalline. A charge-transfer complex was formed from a 1:1 mixture of ketal derivatives with electron-donating and electron-accepting groups, and the 9-anthrylidene derivative in its fibrillar network dimerized upon irradiation. Results demonstrate that subtle changes in the ketal structures can lead to very different aggregation pathways