•A new chiral tetraphenylethene derivative (TPE-DLEU) was synthesized.•TPE-DLEU showed aggregation-induced emission and circular dichroism, and circularly polarized luminescence properties.•TPE-DLEU exhibited the controllable helical self-assembly behaviours.A new chiral tetraphenylethene derivative with two l-leucine-containing attachments, TPE-DLEU, has been designed and synthesized by Cu(I)-catalyzed azide-alkyne cycloaddition “click” reaction. It emits faintly and gives weak circular dichroism (CD) signals in solutions, but shows strong fluorescence and Cotton effects in the aggregated state, showing aggregation-induced emission (AIE) and CD (AICD) characteristics. Furthermore, its film displays circularly polarized luminescence (CPL) with an emission dissymmetry factor of +3.2 × 10−3. Interestingly, TPE-DLEU exhibits controllable helical self-assembly behaviours. It could readily assemble into right-handed helical nanofibers upon the evaporation of its 1,2-dichloroethane (DCE) solution, but form left-handed helical nanofibers by the addition of hexane to its DCE solution.

The self-assembly of π-conjugated molecules into low-dimensional luminescent nanomaterials has attracted much attention for their applications in optoelectronics and photonics. Herein, a new tolane derivative (1) containing donor and acceptor units has been designed and synthesized. The compound 1 shows the effect of intramolecular charge transfer (ICT) due to the donor–acceptor interaction. In solution, it is weakly emissive, but becomes highly emissive upon aggregation, demonstrating the novel phenomenon of aggregation-induced emission (AIE). Moreover, through controlled self-assembly of 1, different micro/nanostructures (ribbons, rods and flower-like clusters) with high emission efficiency can be obtained, which paves the way for its photonic and electronic applications.