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      Rational design of asymmetric red fluorescent probes for live cell imaging with high AIE effects and large two-photon absorption cross sections using tunable terminal groups.

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          Abstract

          In this work, we report the synthesis of a family of donor-acceptor (D-A) π-conjugated aggregation-induced red emission materials (TPABT, DTPABT, TPEBT and DTPEBT) with the same core 2,2-(2,2-diphenylethene-1,1-diyl)dithiophene (DPDT) and different amounts and different strengths of electron-donating terminal moieties. Interestingly, TPABT and TPEBT, which have asymmetric structures, give obviously higher solid fluorescence quantum efficiencies in comparison with those of the corresponding symmetric structures, DTPABT and DTPEBT, respectively. In particular, the thin film of TPEBT exhibited the highest fluorescence quantum efficiency of ca. 38% with the highest αAIE. Moreover, TPEBT and DTPEBT with TPE groups showed two-photon absorption cross-sections of (δ) 1.75 × 103 GM and 1.94 × 103 GM at 780 nm, respectively, which are obviously higher than the other two red fluorescent materials with triphenylamine groups. Then, the one-photon and two-photon fluorescence imaging of MCF-7 breast cancer cells and Hela cells, and cytotoxicity experiments, were carried out with these red fluorescent materials. Intense intracellular red fluorescence was observed for all the molecules using one-photon excitation and for TPABT using two-photon excitation in the cell cytoplasm. Finally, TPEBT is biocompatible and functions well in mouse brain blood vascular visualization. It is indicated that these materials can be used as a specific stain fluorescent probe for live cell imaging.

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          Author and article information

          Journal
          Chem Sci
          Chemical science
          Royal Society of Chemistry (RSC)
          2041-6520
          2041-6520
          Jul 01 2016
          : 7
          : 7
          Affiliations
          [1 ] Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials , School of Chemistry , Beijing Institute of Technology , Beijing , China . Email: jinlwang@bit.edu.cn.
          [2 ] State Key Laboratory of Luminescent Materials and Devices , South China University of Technology , Guangzhou , China . Email: mszjzhao@scut.edu.cn.
          [3 ] School of Chemistry and Chemical Engineering , Huazhong University of Science and Technology , Wuhan , China . Email: louxiaoding@hust.edu.cn.
          [4 ] Department of Chemical and Biomolecular Engineering , National University of Singapore , Singapore 117585.
          Article
          c5sc04920b
          10.1039/c5sc04920b
          6018563
          30155099
          5d965605-1880-4a20-8365-e050550b7cc6
          History

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