A bionic paired hydrogen-bond strategy for extending organic π-conjugation to regulate emission

Abstract

Herein, we first demonstrate a non-covalent strategy that extends the π-conjugation of fluorophores through bionic paired hydrogen-bond interactions. In well-designed molecular models, 1,8-naphtholactam (Np)-equipped molecules (TPE/HTPE-Np) exhibit highly efficient dual-state emission in a red-shifted region, whereas their acenaphthene (Ap)-equipped counterparts (TPE/HTPE-Ap) reserve typical AIE behaviors with short-wavelength emission. Single-crystal and theoretical analyses prove that these bionic hydrogen-bond interactions enable the facile formation of dimeric TPE/HTPE-Np, resulting in their larger delocalized π-electron conjugation, thereby playing a crucial role in their unique emission characteristics.