A small change in molecular structure, a big difference in the AIEE mechanism.

An anthracene carboxamide derivative of the excited-state intramolecular proton-transfer compound of 2-(2'-hydroxyphenyl)benzothiazole has been newly developed to produce the prominent characteristics of aggregation-induced enhanced emission (AIEE) with a high solid-state fluorescence quantum efficiency of 78.1%. Compared with our previously reported phenyl carboxamide derivatives, a small tailoring of the molecular structure was found to result in a big difference in the dominant factor of the AIEE mechanism. In the phenyl carboxamide derivatives, the dominant factor of the AIEE mechanism is the restriction of the twisted intramolecular charge transfer (TICT) of the enol excited state, regardless of their different aggregation modes. In the anthracene carboxamide derivative, N-(3-(benzo[d]thiazol-2-yl)-4-hydroxyphenyl) anthracene-9-carboxamide, the AIEE characteristics are not dependent on the restriction of TICT, but mainly attributed to the cooperative effects of J-aggregation and the restriction of the cis-trans tautomerization in the keto excited state. A specific N···π interaction was found to be the main driving force for this J-aggregation, as revealed by the single crystal analysis. The AIEE mechanism of this anthracene carboxamide derivative was studied in detail through photophysical investigations and theoretical calculations. On the basis of its AIEE characteristics, a stable non-doped organic light-emitting diode was achieved, with high color purity and a remarkably low efficiency roll-off. This journal is © the Owner Societies 2012