Chirality dominance in seeded supramolecular copolymerization of complementary perylenediimides

Abstract

Herein, we report the synthesis and self-assembly behavior of the chiral 3,4,9,10-benzo[d,e]isoquinolino [1,8g,h]quinolinetetracarboxylic diimide (BQQDI) 1. The electron-withdrawing pyridine rings in this PDI-based system enable efficient supramolecular copolymerization with the previously reported chiral PDI 2. Both compounds bear peripheral point chirality and form chiral supramolecular polymers. In addition, intramolecular hydrogen bonding involving peripheral benzamide groups stabilizes the metastable monomeric species M*, which retard homopolymerization into chiral J-type polymers poly-1 and poly-2. Seeding with the corresponding homopolymers promotes kinetically controlled co-assembly, yielding chiral heteropolymers poly-1-co-2 or poly-2-co-1 . Notably, the chirality of the resulting copolymers is dictated by PDI 2, regardless of the seed used.