Synthesis and tunable self-assemblies of peri-naphtho dyes

Abstract

The thesis entitled “Synthesis and tunable self-assemblies of peri-naphtho dyes” is based on the derivatization of peri-naphthoindigo (PNI) dye, an analogue of popular and historic dye indigo. The results of the derivatization process are summarized in to four chapters. Chapter 1 : In the first chapter, a boron difluoride complex of peri-naphthoindigo (PNIBF2) was prepared, and its supramolecular chemistry was studied in both non-polar and polar solvent mixtures. In non-polar solvent mixtures, PNIBF2 aggregates into emissive and linear nanofibres, which have a higher extinction co-efficient compared to the monomer. On the other hand, in polar solvent mixtures, the molecule exhibited supramolecular polymorphism at a specific composition (76/24 water/THF) in which conversion from ellipsoidal to spherical shape was seen via heating and subsequent slow cooling. The polymorphism was accompanied by pathway complexity, and kinetic and thermodynamic forms of the aggregates were identified. This work highlights the potential of PNI derivatives as motifs in dynamic and functional supramolecular systems.