Asymmetric living supramolecular polymerization of an achiral aza-BODIPY dye by solvent-mediated chirality induction and memory

Abstract

The kinetic self-assembly properties of an achiral aza-BODIPY dye 1 bearing two hydrophobic fan-shaped tridodecyloxybenzamide pendants through 1,2,3-triazole linkages was investigated in detail in chiral solvents (S)- and (R)-limonene by...

Functional supramolecular aggregates based on BODIPY and aza-BODIPY dyes: control over the pathway complexity

“…15a). 142 Although spectroscopic studies implied the presence of a kinetic self-assembly pathway of dye 12 in the chiral limonene solvents, the kinetic trapping of the metastable aggregates Agg. I L ("L" represents limonene) could not be achieved owing to its quick transformation into thermodynamically stable H-aggregate Agg.…”

Pathway-dependent supramolecular polymerization by planarity breaking

“…In this context, tetracoordinated organoboron dyes represent an ideal choice to investigate such effects, given that the typically used boron diuoride groups (BF 2 ) are arranged out of plane and, thus, may induce molecular distortions. In addition to the well-known boron dipyrromethene (BODIPY) dyes, [45][46][47][48] where the BF 2 is linked to a dipyrromethene core, various analogous scaffolds, including azaBODIPYs, 12 BODIHYs (hydrazones), 49,50 boron-locked anilido pyridines, 51 bis(borondiuoride)-8-imidazodipyrromethenes (BOIMPYs) 52 and azaBOIMPYs, 53 have been developed to leverage the photophysical properties and applications of this class of dyes. A particularly notable scaffold from the structural viewpoint is the BOPHY core (bis(diuoroboron)-1,2-bis((1H-pyrrol-2-yl) methylene)hydrazine), featuring two BF 2 groups within a tetracyclic pyrrole-boron diuoride structure.…”