Because of their strong accepting nature, PQ-based materials have been explored as fluorescent sensors, as motifs in organic liquid-crystalline semiconductors, and as components in OLEDs and organic photovoltaics (OPV). Chen et al. reported an AIE active fluorescent donor-acceptor system based on PQ derivatives that exhibited green and red emission from their aggregates, and utilized these in bio-imaging applications. Vishwakarma et al. reported a PQ based columnar liquid crystalline material (PQ10) and its use as a fluorescent emitter for green OLEDs. Due to impressive hole transporting mobility of PQ10, it was also used as a hole transporting material for photovoltaic applications. In our bid to design NIR emitters, we decorated the PQ moiety with four electron-donating groups, either dimethylacridane (DMAC) or phenoxazine (PXZ), each separated by a phenylene bridge to the central PQ acceptor. We cross-compare the optoelectronic properties of 4DMAC-TPPQ, and 4PXZ-TPPQ with that of the electron-acceptor TPPQ (Scheme 1), including assessing whether each of these compounds shows aggregation-induced emission enhancement (AIE). TPPQ emits in the blue (λPL = 456 nm) in toluene, while 4DMAC-TPPQ and 4PXZ-TPPQ emit at 650 and 762 nm, respectively (Figure ). Their corresponding DEST values, obtained in glassy 2-MeTHF at 77 K, are 0.97, 0.41 and 0.24 eV. All these compounds show AIE in THF:H2O mixtures; indeed, upon increasing the water fraction in THF solution the blue PL band peaking at 490 nm intensified, which is associated with locally-excited emission from TPPQ. Additionally, for 4DMAC-TPPQ there is the appearance of a deep-red band at 650 nm and for 4PXZ-TPPQ a band at 790 nm emerges, both of which are associated with aggregate formation (Figure ).