One bioprobe: a fluorescent and AIE-active macromolecule; two targets: nucleolus and mitochondria with long term tracking.

Specific organelle imaging and long-term cellular tracking are of paramount importance in monitoring biological processes, pathological pathways, and therapeutic effects, etc. Herein, we report a novel macromolecule fluorescent probe (TPPA-DBO), which is synthesized from tris(4-(pyridin-4-yl)phenyl)amine (TPPA) and 1,8-dibromononane (DBO) with a gram scale by a simple method. TPPA-DBO demonstrates a highly specific nucleolus-targeting ability, which is very challenging in the bioimaging research field. We have shown that the green nucleolus-specificity probe TPPA-DBO has advantages over the commercially available nucleolus-staining probes such as DAPI, Hoechst dyes and SYTOs in terms of its AIE-performance, large Stokes shift (175 nm), excellent photostability, and promising usefulness in live cell imaging experiments. Surprisingly, after internalizing TPPA-DBO into the nucleus region for a period of time, some TPPA-DBO are reversely diffused from nucleolus into the cytoplasm, thus resulting in the staining of mitochondria with a redder emission color. This research result may provide a new concept of cellular tracker design and provide insight into biological questions, understanding disease mechanismss, and designing new therapeutic strategies.