Self-doped and planar nitrogen-bay-functionalized perylene diimides: unravelling structure-property relationships.

ABSTRACT: Bay-functionalization of perylene diimides (PDIs) offers a strategy for modulating electronic properties to achieve optimal n-type charge transport character, but can result in core twisting and reduced planarity, leading to compromised π-conjugation and disruption of tight π-π stacking in the solid state. Herein, we report the synthesis and characterization of two new nitrogen-bay-functionalized N-annulated PDIs, where N-annulation effectively enforces planarity of the polycyclic aromatic core thus preserving π-conjugation even with bulky bay substituents present. Both compounds exhibit intramolecular charge transfer character, tunable optical and electrochemical properties, and strong paramagnetic behaviour without external dopants present, as confirmed by UV-visible spectr

SUBMITTER: Wolfe KM 

PROVIDER: S-EPMC12547978 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature