Tunable Morphology and Mesophase Formation by Naphthalene-Containing Poly(aryl ether) Dendron-Based Low-Molecular-Weight Fluorescent Gels

Abstract

Novel poly(aryl ether) dendron-based low-molecular-weight organogelaters (LMWG) containing naphthalene units at the core have been synthesized, and the self-assembly of the system has been examined in a variety of solvents and solvent mixtures. The compounds readily form gels with attractive critical gel concentration values associated with gelation-induced enhanced emission (GIEE). In addition to the remarkable properties of the previously reported anthracene and pyrene analogues (Rajamalli, P.; Prasad, E. Org. Lett.2011, 13, 3714 and Rajamalli, P.; Prasad, E. Soft Matter2012, 8, 8896), the self-assembled systems exhibit distinctly different structure-property relationships. Unlike the reported ones, the present system forms sheetlike morphology in nonpolar solvent mixtures, giant vesicles in polar solvent mixtures, and lamellar or hexagonal columnar phases in single solvents. The unique properties of the self-assembled systems, which were analyzed through electron microscopic (SEM, TEM, AFM) and spectroscopic techniques (POM, fluorescence), are attributed to the replacement of anthracene/pyrene units by naphthalene units. The present work unravels the subtle role of minute structural change in altering the properties of LMWGs based on poly(aryl ether) dendrons.