Self-Assembly and Electrical Conductivity of a New [1]benzothieno[3,2-b][1]-benzothiophene (BTBT)-Peptide Hydrogel

Molecules. 2023 Mar 24;28(7):2917. doi: 10.3390/molecules28072917.

Abstract

The conjugation of small-molecule semiconductors with self-assembling peptides is a powerful tool for the fabrication of supramolecular soft materials for organic electronics and bioelectronics. Herein, we introduced the benchmark organic semiconductor [1]benzothieno[3,2-b][1]-benzothiophene (BTBT) within the structure of a self-assembling amphipathic peptide. The molecular structure of the conjugate was rationally designed to favour π-π stacking between BTBT cores and π-delocalization within the self-assembled architectures. Hydrogels with fibrillar structure were obtained upon self-assembly. Spectroscopic studies confirmed that both hydrogen bonding between peptide segments and π-π stacking between BTBT chromophores are responsible for the formation of the 3D fibrillar network observed by transmission electron microscopy. The hydrogel was successfully deposited on gold interdigitated electrodes and a conductivity up to 1.6 (±0.1) × 10-5 S cm-1 was measured.

Keywords: [1]benzothieno[3,2-b][1]-benzothiophene; electrically conductive hydrogel; peptide; peptide-chromophore conjugate; supramolecular hydrogel; π-gel.

Grants and funding

S.C. and R.C.H. acknowledge the funding from the University of Padua, Department of Chemical Sciences (P-DiSC#11NexuS_BIRD2020-UNIPD-CARBON-FET-) and from the Italian Ministry of Education, Universities and Research (Nanochemistry for Energy and Health, NExuS, within the national funding network termed “Dipartimenti di Eccellenza”).