Interplay between H‐Bonding and Preorganization in the Evolution of Self‐Assembled Systems

Abstract

Cooperative π–π interactions and H‐bonding are frequently exploited in supramolecular polymerization; however, close scrutiny of their mutual interplay has been largely unexplored. Herein, we compare the self‐assembly behavior of a series of C ₂‐ and C ₃‐symmetrical oligophenyleneethynylenes differing in their amide topology (N‐ or C‐centered). This subtle structural modification brings about drastic changes in their photophysical and supramolecular properties, highlighting the reciprocal impact of H‐bonding vs. preorganization on the evolution and final outcome of supramolecular systems.

Abstract

To match or not to match: Detailed self‐assembly studies of a series of C ₂ ‐ and C ₃ ‐symmetrical π‐systems that differ in the amide connectivity (N‐ vs. C‐centered) were used to examine the reciprocal impact of H‐bonding and preorganization on the evolution of self‐assembled structures.