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Regulation of excitation transitions by molecular design endowing full-color-tunable emissions with unexpected high quantum yields for bioimaging application

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Abstract

Organic fluorophores are indispensible in chemical/biological imaging. The conjugated fluorescent molecules simultaneously possessing highly tunable emission, high quantum yield in solvents of different polarities, and large Stokes shift are quite rare. Herein, we report a new category of fluorophores based on diarylated thieno[3,4-b]thiophenes efficiently synthesized by direct C–H arylation reaction. TbT-Fluors showed full-color-tunable emissions with large Stokes shifts. Intriguingly, the fluorescence quantum yields of TbT-Fluors are barely sensitive to solvent polarities, approaching 100%. Based on photophysical and theoretical investigations, we found that the enhanced oscillator strength of the S1-S0 transition and increased T2-S1 energy difference can sufficiently compensate the negative effect from the decreased energy gap and increased reorganization energy in dimethyl sulfoxide (DMSO). Bioimaging applications revealed that some TbT-Fluors can penetrate the cell membrane and are superior for imaging in terms of high photochemical stability and low cytotoxicity. Furthermore, TbT-PhF exhibits specific colocalization with mitochondria in living cells.

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References

  1. Rettig W, Strehmel B, Schrader S, Seifert H. Applied Fluorescence in Chemistry, Biology, and Medicine. New York: Springer, 1999

    Book  Google Scholar 

  2. de Silva AP, Gunaratne HQN, Gunnlaugsson T, Huxley AJM, McCoy CP, Rademacher JT, Rice TE. Chem Rev, 1997, 97: 1515–1566

    Article  PubMed  Google Scholar 

  3. Lavis LD, Raines RT. ACS Chem Biol, 2008, 3: 142–155

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Lavis LD, Raines RT. ACS Chem Biol, 2014, 9: 855–866

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Bates M, Huang B, Dempsey GT, Zhuang X. Science, 2007, 317: 1749–1753

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Chen Z, Paley DW, Wei L, Weisman AL, Friesner RA, Nuckolls C, Min W. J Am Chem Soc, 2014, 136: 8027–8033

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Mason WT. Fluorescent and Luminescent Probes for Biological Activity. 2nd Ed. London: Academic Press, 1999

    Google Scholar 

  8. Zhang Z, Achilefu S. Org Lett, 2004, 6: 2067–2070

    Article  CAS  PubMed  Google Scholar 

  9. Peng X, Song F, Lu E, Wang Y, Zhou W, Fan J, Gao Y. J Am Chem Soc, 2005, 127: 4170–4171

    Article  CAS  PubMed  Google Scholar 

  10. Loudet A, Burgess K. Chem Rev, 2007, 107: 4891–4932

    Article  CAS  PubMed  Google Scholar 

  11. Choi EJ, Kim E, Lee Y, Jo A, Park SB. Angew Chem Int Ed, 2014, 53: 1346–1350

    Article  CAS  Google Scholar 

  12. Kim E, Lee Y, Lee S, Park SB. Acc Chem Res, 2015, 48: 538–547

    Article  CAS  PubMed  Google Scholar 

  13. Li M, Feng LH, Lu HY, Wang S, Chen CF. Adv Funct Mater, 2014, 24: 4405–4412

    Article  CAS  Google Scholar 

  14. Yamaguchi E, Wang C, Fukazawa A, Taki M, Sato Y, Sasaki T, Ueda M, Sasaki N, Higashiyama T, Yamaguchi S. Angew Chem Int Ed, 2015, 54: 4539–4543

    Article  CAS  Google Scholar 

  15. Wang C, Fukazawa A, Taki M, Sato Y, Higashiyama T, Yamaguchi S. Angew Chem Int Ed, 2015, 54: 15213–15217

    Article  CAS  Google Scholar 

  16. Neto BAD, Carvalho PHPR, Correa JR. Acc Chem Res, 2015, 48: 1560–1569

    Article  CAS  PubMed  Google Scholar 

  17. Cheng Y, Li G, Liu Y, Shi Y, Gao G, Wu D, Lan J, You J. J Am Chem Soc, 2016, 138: 4730–4738

    Article  CAS  PubMed  Google Scholar 

  18. Takimiya K, Osaka I, Nakano M. Chem Mater, 2014, 26: 587–593

    Article  CAS  Google Scholar 

  19. Liu F, Espejo GL, Qiu S, Oliva MM, Pina J, Seixas de Melo JS, Casado J, Zhu X. J Am Chem Soc, 2015, 137: 10357–10366

    Article  CAS  PubMed  Google Scholar 

  20. Zhang C, Zhu X. Acc Chem Res, 2017, 50: 1342–1350

    Article  CAS  PubMed  Google Scholar 

  21. Ren L, Liu F, Shen X, Zhang C, Yi Y, Zhu X. J Am Chem Soc, 2015, 137: 11294–11302

    Article  CAS  PubMed  Google Scholar 

  22. Ren L, Fan H, Huang D, Yuan D, Di CA, Zhu X. Chem Eur J, 2016, 22: 17136–17140

    Article  CAS  PubMed  Google Scholar 

  23. Haugland RP. Handbook of Fluorescent Probes and Research Products. 9th Ed. City of Eugene, Oregon: Molecular Probes, Inc., 2003

    Google Scholar 

  24. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, NakajimaT, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, DapprichS, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09. Revision D01. Walling-ford, CT: Gaussian, Inc., 2009

    Google Scholar 

  25. Lu T. sobMECP Program. thttp://sobereva.com/286

  26. Harvey JN, Aschi M, Schwarz H, Koch W. Theor Chem Accounts-Theor Computation Modeling (Theoretica Chim Acta), 1998, 99: 95–99

    Article  CAS  Google Scholar 

  27. Mataga N, Yao H, Okada T, Rettig W. J Phys Chem, 1989, 93: 3383–3386

    Article  CAS  Google Scholar 

  28. Schütz M, Schmidt R. J Phys Chem, 1996, 100: 2012–2018

    Article  Google Scholar 

  29. Einstein A. Physik Z, 1917, 18: 121–128

    CAS  Google Scholar 

  30. Xie Y, Zhang T, Li Z, Peng Q, Yi Y, Shuai Z. Chem Asian J, 2015, 10: 2154–2161

    Article  CAS  PubMed  Google Scholar 

  31. Zhang T, Ma H, Niu Y, Li W, Wang D, Peng Q, Shuai Z, Liang WZ. J Phys Chem C, 2015, 119: 5040–5047

    Article  CAS  Google Scholar 

  32. Uoyama H, Goushi K, Shizu K, Nomura H, Adachi C. Nature, 2012, 492: 234–238

    Article  CAS  PubMed  Google Scholar 

  33. Ho YP, Kung MC, Yang S, Wang TH. Nano Lett, 2005, 5: 1693–1697

    Article  CAS  PubMed  Google Scholar 

  34. Rong Y, Wu C, Yu J, Zhang X, Ye F, Zeigler M, Gallina ME, Wu IC, Zhang Y, Chan YH, Sun W, Uvdal K, Chiu DT. ACS Nano, 2013, 7: 376–384

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  35. Jiang K, Sun S, Zhang L, Lu Y, Wu A, Cai C, Lin H. Angew Chem Int Ed, 2015, 54: 5360–5363

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the National Basic Research Program of China (2014CB643502), the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB12010200), and the National Natural Science Foundation of China (91333113, 21572234).

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Authors and Affiliations

  1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China

    Feng Liu, Shengliang Li, Ruihong Duan, Shuhai Qiu, Yuanping Yi, Shu Wang & Xiaozhang Zhu

  2. University of Chinese Academy of Sciences, Beijing, 100049, China

    Feng Liu, Ruihong Duan, Shu Wang & Xiaozhang Zhu

Authors
  1. Feng Liu
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  2. Shengliang Li
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  3. Ruihong Duan
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  4. Shuhai Qiu
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  5. Yuanping Yi
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  6. Shu Wang
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  7. Xiaozhang Zhu
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Corresponding authors

Correspondence to Yuanping Yi, Shu Wang or Xiaozhang Zhu.

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11426_2017_9159_MOESM1_ESM.pdf

Regulation of Excitation Transitions by Molecular Design En-dowing Full-Color-Tunable Emissions with Unexpected High Quantum Yields for Bioimaging Application

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Liu, F., Li, S., Duan, R. et al. Regulation of excitation transitions by molecular design endowing full-color-tunable emissions with unexpected high quantum yields for bioimaging application. Sci. China Chem. 61, 418–426 (2018). https://doi.org/10.1007/s11426-017-9159-7

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  • DOI: https://doi.org/10.1007/s11426-017-9159-7

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