A series of BODIPY-based AIEgens (QB1−QB5 and Bis-QB) containing 2-(2-hydroxyphenyl)quinazoline have been synthesized and thoroughly characterized. Photophysical properties of these compounds in solution and the aggregated state have been meticulously investigated and fine-tuned via structural modifications. These display green emission (∼530 nm) in solution and bright red emission (600−655 nm) in the aggregated/solid state with increased quantum yield. Crystal structure analyses and spectral studies revealed efficient J-type aggregation in these derivatives. Significant impact of 2-(2hydroxyphenyl)quinazoline toward modulating intermolecular interactions and facilitating J-type stacking between BODIPY units has also been established. Moreover, the essential role of excited-state intramolecular proton transfer (ESIPT) in inducing emission in the aggregated state and tuning of ESIPT emission by variation of substituents have been supported by various studies.

1,7-Phenanthroline based bis−boron dipyrromethenes (bis−BODIPYs) B1 and B2 obtained via small substitutional changes (−Cl/–SCH3) have been described. The effect of restriction of intramolecular rotation (RIR) in emission enhancement in a viscous solvent (glycerol) has been studied besides the vital role of intermolecular interactions scrutinized by X-ray single-crystal studies. The efficiency of intersystem crossing (ISC) in the generation of singlet oxygen (ΦΔ ∼ 19.2% and 56.7%) by photoirradiation using visible light along with distinct photostability has been investigated by 1,3-diphenylisobenzofuran (DPBF) titration studies. The 1O2 generation quantum yield and photosensitizing durability of the bis−BODIPYs have been investigated by photooxidation of 1,5-dihydroxynaphthalene (DHN) in the presence of B1 and B2 as photosensitizers. The pseudo-first-order rate constants for photooxidation reactions and consumption rates of DHN reflected appreciable 1O2 generation quantum yields (ΦΔ: B1, 29.0; B2, 57.8%). Density functional theory (DFT) studies showed the distribution of electron density over the dipyrrin moiety. Overall results indicated that these new photosensitizers (PSs) may be very promising in photodynamic therapy of tumors, photobiology, and organic photochemistry.

The hydrazone based BF2–complexes (BODIHYs; B1–B2) have been synthesized and their photophysical and aggregation behavior have been established. These BODIHYs have been showed light harvesting properties in presence of RhB as acceptor.

A series of ESIPT (excited state intramolecular proton transfer) active systems (HQz1-HQz6) derived from quinazoline have been reported. The ESIPT emission for these derivatives gets completely quenched in solvents with diverse polarities which have been restored via aggregation-induced emission (AIE) with large Stokes shift (up to 314 nm). It varied from 450 to 701 nm just by altering substituents at the para position of hydroxy group in the central phenyl ring. As well, HQz1-HQz6 displayed solid state emission [∼455 (blue) to ∼704 nm (red)]. The formyl group on the central hydroxy-phenyl ring of these derivatives induces ESIPT by increasing acidity of the hydroxy proton which has been followed by H NMR studies. Further, it has been clearly shown that emission colour and aggregate morphology can be fine tuned by incorporating apt substituents. The present study offers a simple route to obtain colour tunable ESIPT emission via AIE which is very important for biological imaging and fabrication of optoelectronic devices.

In this work, we present tetraphenylimidazole-based BODIPYs (HPIB1–HPIB4) as fluorescent molecular rotors exhibiting aggregation induced emission, solid state fluorescence and appreciable sensitivity towards viscosity.