Bolapolyphiles via Click Reaction: Effect of Flexible Polyaromatic Backbone Involving Polar Hydrogen Bonding Units on Their Self‐assembly

Abstract

AbstractThree series of bolapolyphiles consisting of a flexible diphenylthiophene polyaromatic backbone involving hydrogen bonding triazole units and two terminal glycerol groups as well as lateral alkyl chains (being either linear or branched) have been synthesized by CuAAC click reaction. The effect of the flexible polyaromatic backbone, as well as the length, number and branching or linearity of the lateral chain on their self‐assembly was investigated. The backbone flexibility led to the formation of structures intermediate between the well defined honeycombs of the rigid bolapolyphiles and the conventional flexible amphiphiles. T‐shaped bolapolyphiles with one lateral chain occupied small volume (one branched chain or one short linear chain) display triangular honeycomb phases. Whereas T‐shaped or π‐shaped bolapolyphiles with one or two lateral chain occupied larger volume (one longer linear or two linear chain) display square honeycomb phases with diffused or less defined cylinder wall structures. Further these compounds can self assemble into organogels in organic solvents. Their photophysical properties are affected greatly by the type of lateral chains, and they can act as chemosensors towards Fe3+.