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

Chemical Science
Zheng-Feng ChangBen Zhong Tang

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 ...Continue Reading

References

Sep 21, 2002·Chemical Communications : Chem Comm·J LuoB Z Tang
Feb 8, 2013·Chemical Communications : Chem Comm·Jian ZhouBen Zhong Tang
Jun 8, 2013·Accounts of Chemical Research·Dan DingBen Zhong Tang
Dec 18, 2013·Journal of the American Chemical Society·Kang CaiDahui Zhao
Feb 25, 2014·Inorganic Chemistry·Xue-Lian XinFuyou Li
Mar 26, 2014·Nanoscale·Nyssa T EmersonHaw Yang
Apr 16, 2014·Chemical Society Reviews·Rongrong HuBen Zhong Tang
Jun 4, 2014·Angewandte Chemie·Hai-Yu HuCarsten Schultz
Nov 2, 2014·Advanced Materials·Changhyun PangZhenan Bao
Nov 7, 2014·Chemical Society Reviews·Ryan T K KwokBen Zhong Tang
Feb 7, 2015·Chemical Communications : Chem Comm·Xiaobiao DongDeqing Zhang
Feb 18, 2015·Chemical Society Reviews·Jing LiangBin Liu
May 12, 2015·Angewandte Chemie·Aleksander RebaneMerle Uudsemaa
Jun 9, 2015·Chemical Communications : Chem Comm·Ming ChenBen Zhong Tang
Jul 8, 2015·Journal of the American Chemical Society·Christopher M LemonDaniel G Nocera
Aug 4, 2015·Chemical Communications : Chem Comm·Dongdong LiJihong Yu
Oct 22, 2015·Journal of the American Chemical Society·Zi-Ru DaiLing Yang
Oct 30, 2015·Journal of the American Chemical Society·Sicong WuYao He
Dec 2, 2015·Nature Communications·Jie LiuAlan J Heeger
Oct 1, 2015·Chemical Science·Zujin ZhaoBen Zhong Tang
Mar 1, 2015·Chemical Science·Ming ChenBen Zhong Tang
Jul 1, 2015·Chemical Science·Subhankar SinghaKyo Han Ahn
Sep 7, 2014·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Yanqiu LiuYupeng Tian

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Citations

Dec 1, 2018·Organic & Biomolecular Chemistry·Pan LiLeilei Tian
Jul 1, 2016·Small·Xiaoding LouBen Zhong Tang
Jul 25, 2019·Chemistry : a European Journal·Olena VakuliukDaniel T Gryko
Jul 21, 2016·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Bing GuoBin Liu
Jan 12, 2021·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Yuping ZhouRuiyuan Liu

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Methods Mentioned

BETA
fluorescence imaging
fluorescence microscopy
fluorescence imaging microscopy
nanoprecipitation

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