Tetraphenylethene end-capped diketopyrrolopyrrole fluorogens with AIE and large two-photon absorption cross-sections features and application in bioimaging

•Four diketopyrrolopyrrole-based derivatives were synthesized and characterized.•These dyes have aggregation-induced emission and two-photon absorption properties.•DPP-TPE-3 has the largest two-photon absorption cross sections (σ = 1140 GM).•DPP-TPE-3 can be used as an effective florescence probe for bioimaging.

In this work, a series of new diketopyrrolopyrrole-based dyes have been synthesized by connecting tetraphenylethene to the diketopyrrolopyrrole core. All the four compounds exhibit good aggregation-induced emission property with nonemissive in the solution but strong red fluorescence in the aggregate or solid state. Also, these new dyes exhibit large two-photon absorption cross sections (σ), in which the σ data measured by the open aperture Z-scan technique are determined to be 150, 300, 1140 and 1016 GM for four dyes, respectively. In addition, compound with stilbene and four tetraphenylethene units (DPP-TPE-3) was used as the luminogen and encapsulated into nanoparticles for cell imaging and two-photon excited fluorescence blood vessels imaging. The result indicates that it can be used as the effective fluorescence probe for bioimaging and has great potential for bioapplications.

Graphical abstractA series of new DPP-based derivatives DPP-TPE-(1-4) were designed and synthesized. These dyes show excellent AIE and 2PA properties, in which the success of the cell imaging and blood vessels imaging used by the DPP-TPE-3 as the luminogen indicates that it can be used as the effective fluorescence probe for bioimaging and has great potential for bioapplications.Figure optionsDownload full-size imageDownload as PowerPoint slide