A new aggregation-induced emission (AIE) luminogen is obtained by dimerizing acridin-9(10H)-one (Ac), an aggregation-caused quenching (ACQ) effect monomer via an N─N bond and forming 9H,9'H-[10,10'-biacridine]-9,9'-dione (DiAc) with D2d symmetry. The quenching of DiAc in solution is ascribed to the enhanced basicity promoting hydrogen bonding and then a hydrogen abstraction (HA) reaction and/or an unallowed transition in frontier orbitals with the same symmetry facilitating intersystem crossing. It is found that emissive Ac is one product of the non-emissive DiAc solution in the HA reaction activated by UV irradiation. By exploiting the AIE properties and the HA reaction of DiAc, photolithographic patterning is demonstrated with a paper wetted with DiAc solution.
Keywords: acridone derivatives; aggregation‐induced emission; conformation; hydrogen atom transfer; isotope effects.
© 2024 The Author(s). Advanced Science published by Wiley‐VCH GmbH.