Aggregation-induced emission enhancement materials with large red shifts and their self-assembled crystal microstructures

Two simple intramolecular charge transfer compounds (BzBMN and BzFAN), derived from 2-benzyloxy-4-diethylaminobenzaldehyde, have been synthesized. Unlike typical AIEE molecules, the enhanced emission of these compounds in the solid state is accompanied by large red shifts in emission wavelength. Absorption and photoluminescence (PL) spectra of the compounds in solution, film and the X-ray single crystal structures were investigated to understand the mechanism of enhanced emission in the solid state. The results indicate that the bathochromic shift excimer-like emissions originated from dimers induced by the dipole-dipole interaction and long-range ordered arrangement (e.g. J-aggregation), and the enhanced emission is attributed to the restriction of intramolecular rotations caused by multiple intermolecular hydrogen bonding interactions. In addition, it was also observed that BzBMN and BzFAN can facilely form single crystal microbelts and microtubes by a simple reprecipitation method. © The Royal Society of Chemistry 2011.