Guiding Suprastructure Chirality of an Oligothiophene by a Single Amino Acid

Within the present work, synthesis and properties of three stereoisomeric hybrid materials consisting of a π-conjugated oligothiophene backbone and a single amino acid (proline), which is attached by click chemistry, are described. The hybrids were in particular investigated regarding their self-assembling behavior in solution. From optical investigations, including circular dichroism spectroscopy, the formation of chiral suprastructures could be deduced and correlated with the stereochemistry of the proline residue. In addition, an elaborate theoretical model of the compounds’ self-assembly into suprastructures was developed on the basis of the experimental findings.