O-acylated/alkylated-modified tetraphenylethene- triphenylamine containing chalcone type AIEgen with solid-state...

Organic solid-state emitters are potential candidates for various optoelectronic and biomedical applications. In this manuscript, four novel O-acylated/alkylated-modified tetraphenylethene-triphenylamine containing chalcone derivatives (TCl, TClB, TBC and TB) have been readily synthesized. Single crystal datas reveal that intermolecular interactions enhance rigidify the molecular conformation and prohibit the intramolecular rotation, leading to highly emissive behaviors in the solid state. Four derivatives (TCl, TClB, TBC and TB) showed the typical AIE feature and could be mechanically ground accompanying a slight spectral shift. In contrast to TBC and TB, O-acylated of the substituents (TCl and TClB) leads to red-shift emission (λ_em,TCL > λ_em,TCLB > λ_em,TB > λ_em,TBC) in the solid/aggregation state that might be originate from distinct packing modes induced by different substituents. Furthermore, TBC and TB can also be applied for imaging in live NALM-6 cells owing to its effective cell permeability. All the above results implied that four derivatives have excellent solid-state emission properties and potential bioimaging applications.