Self‐Aggregation of a Naphthalene‐Monoimide Amphiphile and Its Charge‐Transfer‐Complex Driven Morphogenesis in Water

Abstract A detailed study on the self‐assembly of a naphthalene‐monoimide (NMI)‐containing amphiphile (A‐1) in aqueous medium is reported. The amphiphile forms micelles at a lower concentration and, with an increase in concentration, the micelles are transformed into vesicles. A detailed thermodynamic study reveals that the micelle‐to‐vesicle transformation is a spontaneous and entropy driven process. In the presence of an electron donor, 1,5‐dihydroxynaphthalene (DHN), the vesicles further transformed into tape‐like aggregates. A‐1 and DHN form a 1 : 1 charge‐transfer complex as shown from the ITC and absorption spectroscopic data. The charge‐transfer complexation was also found to be a thermodynamically favorable process. The tapes obtained from the charge‐transfer complexes were found to be more conductive that of the vesicles. Various spectroscopic, microscopic, ITC, XRD, and other techniques were utilized to reveal the underlying self‐assembly mechanism.