Easy access to new anthracenyl π-conjugates: generation of distinct AIE-active materials

Abstract

Inspired by the well-established distyryl anthracenyl (DSA) π-conjugates as aggregation-induced emission active (AIE) materials and the evolution of the synthesis/optoelectronic properties of numerous anthracene-based π-conjugates, a new series of 9-or 10-(hetero)arylated anthracenyl π-conjugates were synthesized using a straightforward and metal-free protocol by starting with a unique family of organophosphonates. The fluorescence behaviors of these (hetero)arylated π-conjugates were systematically studied to determine their AIE-activities, resulting in a new class of much smaller anthracene-based AIEgens. Considerable effort was made to analyze the AIE-behaviors of selected molecules by performing single crystal X-ray diffraction, time-resolved fluorescence, and dynamic light scattering studies. Our mechanistic investigations reveal that the heteroarene(s) linked to a π-conjugated system facilitate the AIE-behaviors of these molecules. Fluorescence microscopy images of the selected compounds in both molecular and aggregated form were obtained to demonstrate their structure–property relationship. Further, a trisubstituted anthracene-based π-conjugate was synthesized and established as a new AIEgen.