Advertisement

Science China Chemistry

, Volume 60, Issue 5, pp 607–613 | Cite as

A luminescence molecular switch via modulation of PET and ICT processes in DCM system

  • Jinfeng Yang
  • Meng Li
  • Lihua Kang
  • Weihong Zhu
Articles

Abstract

A novel versatile dicyanomethylene-4H-pyran (DCM) based derivative bearing ferrocenyl group (DCM-N-Fc) is designed as modulator to construct “off-on” logic operation. The optical properties of DCM-N-Fc are characterized by absorption and steady-state fluorescence technique, showing that the fluorescence from DCM chromophore via intramolecular charge transfer (ICT) is strongly quenched by photoinduced electron transfer (PET) process from ferrocene moiety. In contrast with the references (DCM-N and DCM-Fc), the fluorescence of DCM-N-Fc can be triggered by oxidizing ferrocenyl unit either chemically or electrochemically, exhibiting a characteristic emission modulation at around 610 nm with an electrofluorochromic behavior. Furthermore, the free energy and the fluorescence lifetime in the PET path verify the thermodynamic feasibility. Cyclic voltammetry, absorption spectroscopy, time-resolved fluorescence as well as DFT calculation have been used to elaborate the manipulation via both PET and ICT processes.

Keywords

dicyanomethylene-4H-pyran luminescence redox switch ferrocene 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Notes

Acknowledgments

This work was supported by the National Key Research and Development Program (2016YFA0200300), the National Natural Science Foundation of China for Distinguished Young Scholars (21325625) and Key Project (21636002), Natural Science Foundation of China (1607044), Oriental Scholarship, Fundamental Research Funds for the Central Universities (WJ1416005, 2016 MS108), Science and Technology Commission of Shanghai Municipality (15XD1501400).

Supplementary material

11426_2016_500_MOESM1_ESM.docx (551 kb)
A luminescence molecular switch via modulation of PET and ICT processes in DCM system

References

  1. 1.
    Chen X, Zhou Y, Peng X, Yoon J. Chem Soc Rev, 2010, 39: 2120–2135CrossRefGoogle Scholar
  2. 2.
    Liang J, Feng G, Kwok RTK, Ding D, Tang B, Liu B. Sci China Chem, 2016, 59: 53–61CrossRefGoogle Scholar
  3. 3.
    Fegade U, Bhosale J, Sharma H, Singh N, Bendre R, Kuwar A. J Fluoresc, 2015, 25: 819–824CrossRefGoogle Scholar
  4. 4.
    Wang H, Wang H, Liu C, Duan X, Li Z. Sci China Chem, 2016, 59: 83–88CrossRefGoogle Scholar
  5. 5.
    Wu L, Wang S, Song Y, Wang X, Yan X. Sci China Chem, 2016, 59: 30–39CrossRefGoogle Scholar
  6. 6.
    Melomedov J, Ochsmann JR, Meister M, Laquai F, Heinze K. Eur J Inorg Chem, 2014, 2014: 1984–2001CrossRefGoogle Scholar
  7. 7.
    Zhong F, Yuan X, Zhao J, Wang Q. Sci China Chem, 2016, 59: 70–77CrossRefGoogle Scholar
  8. 8.
    Li Y, Zhang J, Xu C, Zhou Y. Sci China Chem, 2016, 59: 95–105CrossRefGoogle Scholar
  9. 9.
    Fu Y, Xu W, He Q, Cheng J. Sci China Chem, 2016, 59: 3–15CrossRefGoogle Scholar
  10. 10.
    Kumar CK, Trivedi R, Ravi Kumar K, Giribabu L, Sridhar B. J Organomet Chem, 2012, 718: 64–73CrossRefGoogle Scholar
  11. 11.
    Khalid H, Wang L, Yu H, Akram M, Abbasi NM, Sun R, Saleem M, Zain-ul-Abdin M, Chen Y. J Inorg Organomet Polym, 2015, 25: 1511–1520CrossRefGoogle Scholar
  12. 12.
    Gao M, Xie P, Wang L, Miao X, Guo F. Res Chem Intermed, 2015, 41: 9673–9685CrossRefGoogle Scholar
  13. 13.
    Liu Y, Qiao Q, Zhao M, Yin W, Miao L, Wang L, Xu Z. Dyes Pigments, 2016, 133: 339–344CrossRefGoogle Scholar
  14. 14.
    Bairi P, Chakraborty P, Roy B, Nandi AK. Sensor Actuat B-Chem, 2014, 193: 349–355CrossRefGoogle Scholar
  15. 15.
    Georgiev NI, Asiri AM, Qusti AH, Alamry KA, Bojinov VB. Dyes Pigments, 2014, 102: 35–45CrossRefGoogle Scholar
  16. 16.
    Cao J, Feng J, Wu S. Chin J Polym Sci, 2014, 32: 371–376CrossRefGoogle Scholar
  17. 17.
    Lu X, Zhu W, Xie Y, Li X, Gao Y, Li F, Tian H. Chem Eur J, 2010, 16: 8355–8364CrossRefGoogle Scholar
  18. 18.
    Gan J, Tian H, Wang Z, Chen K, Hill J, Lane PA, Rahn MD, Fox AM, Bradley DDC. J Organomet Chem, 2002, 645: 168–175CrossRefGoogle Scholar
  19. 19.
    de Silva AP. J Phys Chem Lett, 2011, 2: 2865–2871CrossRefGoogle Scholar
  20. 20.
    Dimov SM, Georgiev NI, Asiri AM, Bojinov VB. J Fluoresc, 2014, 24: 1621–1628CrossRefGoogle Scholar
  21. 21.
    Zong L, Song Y, Li Q, Li Z. Sensor Actuat B-Chem, 2016, 226: 239–244CrossRefGoogle Scholar
  22. 22.
    Cai Y, Gao Y, Luo Q, Li M, Zhang J, Tian H, Zhu WH. Adv Opt Mater, 2016, 4: 1410–1416CrossRefGoogle Scholar
  23. 23.
    Zhai X, Yu H, Wang L, Deng Z, Abdin Z, Tong R, Yang X, Chen Y, Saleem M. Appl Organometal Chem, 2016, 30: 62–72CrossRefGoogle Scholar
  24. 24.
    Roemer M, Kang YK, Chung YK, Lentz D. Chem Eur J, 2012, 18: 3371–3389CrossRefGoogle Scholar
  25. 25.
    Sakamoto R, Murata M, Nishihara H. Angew Chem Int Ed, 2006, 45: 4793–4795CrossRefGoogle Scholar
  26. 26.
    Kwak G, Wang S, Choi MS, Kim H, Choi KH, Han YS, Hur Y, Kim SH. Dyes Pigments, 2008, 78: 25–33CrossRefGoogle Scholar
  27. 27.
    Guo Z, Zhu W, Tian H. Chem Commun, 2012, 48: 6073–6084CrossRefGoogle Scholar
  28. 28.
    Tian Z, Liu Y, Tian B, Zhang J. Res Chem Intermed, 2015, 41: 525–533CrossRefGoogle Scholar
  29. 29.
    Hu R, Yang C, Wang Y, Lin G, Qin W, Ouyan Q, Law WC, Nguyen QT, Yoon HS, Wang X, Yong KT, Tang BZ. Nano Res, 2015, 8: 1563–1576CrossRefGoogle Scholar
  30. 30.
    Sun W, Fan J, Hu C, Cao J, Zhang H, Xiong X, Wang J, Cui S, Sun S, Peng X. Chem Commun, 2013, 49: 3890–3892CrossRefGoogle Scholar
  31. 31.
    Zhang Y, Huang X, Liu W, Zhang G, Zhang D, Jiang X. Sci China Chem, 2016, 59: 106–113CrossRefGoogle Scholar
  32. 32.
    Sheng X, Chen D, Cao M, Zhang Y, Han X, Chen X, Liu S, Chen H, Yin J. Chin J Chem, 2016, 34: 594–598CrossRefGoogle Scholar
  33. 33.
    Guo Z, Zhu W, Zhu M, Wu X, Tian H. Chem Eur J, 2010, 16: 14424–14432CrossRefGoogle Scholar
  34. 34.
    Zhu W, Huang X, Guo Z, Wu X, Yu H, Tian H. Chem Commun, 2012, 48: 1784–1786CrossRefGoogle Scholar
  35. 35.
    Barbon A, Bott ED, Brustolon M, Fabris M, Kahr B, Kaminsky W, Reid PJ, Wong SM, Wustholz KL, Zanré R. J Am Chem Soc, 2009, 131: 11548–11557CrossRefGoogle Scholar
  36. 36.
    Liu B, Li X, Liu M, Ning Z, Zhang Q, Li C, Müllen K, Zhu W. Dyes Pigments, 2012, 94: 23–27CrossRefGoogle Scholar
  37. 37.
    Franco S, Garín J, Martínez de Baroja N, Pérez-Tejada R, Orduna J, Yu Y, Lira-Cantú M. Org Lett, 2012, 14: 752–755CrossRefGoogle Scholar
  38. 38.
    Guo Z, Zhu W, Shen L, Tian H. Angew Chem Int Ed, 2007, 46: 5549–5553CrossRefGoogle Scholar
  39. 39.
    Guo Z, Zhu W, Xiong Y, Tian H. Macromolecules, 2009, 42: 1448–1453CrossRefGoogle Scholar
  40. 40.
    Guo Z, Zhu W, Tian H. Macromolecules, 2010, 43: 739–744CrossRefGoogle Scholar
  41. 41.
    Thiagarajan V, Ramamurthy P, Thirumalai D, Ramakrishnan VT. Org Lett, 2005, 7: 657–660CrossRefGoogle Scholar
  42. 42.
    Wu X, Sun X, Guo Z, Tang J, Shen Y, James TD, Tian H, Zhu W. J Am Chem Soc, 2014, 136: 3579–3588CrossRefGoogle Scholar
  43. 43.
    Wu X, Shao A, Zhu S, Guo Z, Zhu W. Sci China Chem, 2016, 59: 62–69CrossRefGoogle Scholar
  44. 44.
    Liu Y, Han M, Zhang HY, Yang LX, Jiang W. Org Lett, 2008, 10: 2873–2876CrossRefGoogle Scholar
  45. 45.
    Song C, Yang B, Yang Y, Wang L. Sci China Chem, 2016, 59: 16–29CrossRefGoogle Scholar
  46. 46.
    Wang C, Zhang H, Tian L, Zhu W, Lan Y, Li J, Wang H, Zhang G, Zhang D, Yuan S, Li G. Sci China Chem, 2016, 59: 89–94CrossRefGoogle Scholar
  47. 47.
    Guliyev R, Coskun A, Akkaya EU. J Am Chem Soc, 2009, 131: 9007–9013CrossRefGoogle Scholar
  48. 48.
    Li Q, Guo R, Lin W. J Fluoresc, 2016, 26: 1077–1081CrossRefGoogle Scholar
  49. 49.
    Galangau O, Fabre-Francke I, Munteanu S, Dumas-Verdes C, Clavier G, Méallet-Renault R, Pansu RB, Hartl F, Miomandre F. Electrochim Acta, 2013, 87: 809–815CrossRefGoogle Scholar
  50. 50.
    Khan TK, Pissurlenkar RRS, Shaikh MS, Ravikanth M. J Organomet Chem, 2012, 697: 65–73CrossRefGoogle Scholar
  51. 51.
    Fery-Forgues S, Delavaux-Nicot B. J Photochem Photobiol A-Chem, 2000, 132: 137–159CrossRefGoogle Scholar
  52. 52.
    Zhang L, Zhang D, Zhan S, Yang P, Yang G, Huang Z, Lee YS. Macromol Res, 2012, 20: 212–215CrossRefGoogle Scholar
  53. 53.
    Lin LR, Xu QJ, Wu X, Huang RB, Zheng LS. J Fluoresc, 2011, 21: 1319–1324CrossRefGoogle Scholar
  54. 54.
    Shiga M, Motoyama I, Hata K. Bull Chem Soc Jap, 1968, 41: 1891–1896CrossRefGoogle Scholar

Copyright information

© Science China Press and Springer-Verlag Berlin Heidelberg 2017

Authors and Affiliations

  • Jinfeng Yang
    • 1
    • 2
  • Meng Li
    • 3
  • Lihua Kang
    • 2
  • Weihong Zhu
    • 1
  1. 1.Shanghai Key Laboratory of Functional Materials Chemistry; Key Laboratory for Advanced Materials and Institute of Fine Chemicals; School of Chemistry and Molecular EngineeringEast China University of Science and TechnologyShanghaiChina
  2. 2.Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan; College of Chemistry and Chemical EngineeringShihezi UniversityShiheziChina
  3. 3.School of Environmental Science and EngineeringNorth China Electric Power UniversityBaodingChina

Personalised recommendations