First in situ vesicular self-assembly of ‘binols’ generated by a two-component aerobic oxidation reaction

Abstract

Generation of vesicular self-assemblies from natural and synthetic components has been in the frontiers of research in recent years for an improved understanding of the self-assembly process and also because of its prospective and realized applications in the areas of advanced materials, biotechnology and medicine. In the present work, we report the first example of the in situ generation of vesicular self-assemblies during an aerobic coupling reaction. The two precursor 2-naphthol units, having hydrogen bond donor–acceptor groups with appended alkyl chains, yielded binol (2,2′-dihydroxy-1,1′-binaphthyl) derivatives by aerobic coupling that spontaneously self-assembled in situ, yielding vesicular self-assemblies and gels. The morphology of the self-assemblies has been characterized by various optical, electron and atomic force microscopic techniques. The vesicular self-assemblies obtained in the liquids were capable of entrapping fluorophores such as rhodamine-B and carboxy fluorescein including the anticancer drug doxorubicin. The entrapped fluorophores could also be released by sonication or by rupture of vesicles. The supramolecular gels obtained in binary solvent mixtures showed improved gelation abilities with increase in the alkyl chain lengths as reflected by their minimum gelator concentration (mgcs) values, gel to sol transition temperatures (T_gel) and rheology properties. The results described here are also the first demonstration of gelation during an aerobic coupling reaction.