The pH- and salt-controlled self-assembly of [1]benzothieno[3,2-b][1]-benzothiophene–peptide conjugates in supramolecular hydrogels

Abstract

Here, we report a [1]benzothieno[3,2-b][1]-benzothiophene (BTBT) derivative functionalized with a β-sheet-forming peptide which alternates in its sequence Phe and Glu residues. The BTBT core is a popular structural motif in the design of high-mobility organic semiconductors. The insertion of the self-assembling subunit allows control of the supramolecular organization. This molecule self-assembles in water to give hydrogels over a broad range of pH values. Hydrogelation is triggered by both pH changes and variations in salt concentrations. Transmission electron microscopy shows the formation of long-range self-assembled 1D structures. The key role of hydrogen bonding and π–π interactions in hierarchical self-assembly is investigated using absorption, emission, infrared and circular dichroism spectroscopy. This is the first example of demonstrating the formation of supramolecular hydrogels containing the BTBT structure.