Advertisement

Research on Chemical Intermediates

, Volume 45, Issue 4, pp 2429–2439 | Cite as

Two stimulus-responsive carbazole-substituted D–π–A pyrone compounds exhibiting mechanochromism and solvatochromism

  • Dongqi Liu
  • Yuqi Cao
  • Xilong YanEmail author
  • Bowei WangEmail author
Article
  • 83 Downloads

Abstract

Two D–A compounds were designed and synthesized from 2,6-dimethyl-4-pyrone and carbazole compounds. Both of them exhibited unique fluorescence properties in the aggregated state. Red shifts of the spectrum of 102 nm and 130 nm were observed for BCSP and CSP on changing the solvent from n-hexane to N,N-dimethylformamide (DMF), viz. solvatochromism. This phenomenon induced by the intramolecular charge transfer (ICT) effect was confirmed by density functional theory calculations. Interestingly, they both displayed excellent blue-shifted mechanochromic behavior, which was investigated by powder x-ray diffraction (PXRD) analysis. The results of this study provide a new avenue for the design of organic mechanochromic materials that exhibit a blue-shifting chromatic trend. Based on the unusual response of the solid fluorescence to external mechanical forces, we believe that these materials may be useful in various regards for potential applications.

Keywords

Pyrone Mechanofluorochromic Solvatochromism Blue-shifted 

Notes

Supplementary material

11164_2019_3742_MOESM1_ESM.docx (869 kb)
Supplementary material 1 (DOCX 870 kb)

References

  1. 1.
    P. Alam, V. Kachwal, I.R. Laskar, Sens. Actuators B 228, 539 (2016)CrossRefGoogle Scholar
  2. 2.
    J. Sim, H. Lee, K. Song, S. Biswas, A. Sharma, G.D. Sharma, J. Ko, J. Mater. Chem. C 4, 3508 (2016)CrossRefGoogle Scholar
  3. 3.
    H. Soleimaninejad, M.Z. Chen, X. Lou, T.A. Smith, Y. Hong, Chem. Commun. 53, 2874 (2017)CrossRefGoogle Scholar
  4. 4.
    D. Ding, K. Li, B. Liu, B.Z. Tang, Acc. Chem. Res. 46, 2441 (2013)CrossRefGoogle Scholar
  5. 5.
    B. Guo, X. Cai, S. Xu, S.M.A. Fateminia, J. Liu, J. Liang, G. Feng, W. Wua, B. Liu, J. Mater. Chem. B 4, 4690 (2016)CrossRefGoogle Scholar
  6. 6.
    B.Z. Tang, X. Zhan, G. Yu, P.P.S. Lee, Y. Liu, D. Zhu, J. Mater. Chem. 11, 2974 (2001)CrossRefGoogle Scholar
  7. 7.
    Y. Wang, D. Xu, H. Gao, Y. Wang, X. Liu, A. Han, C. Zhang, L. Zang, Dyes Pigments 156, 291 (2018)CrossRefGoogle Scholar
  8. 8.
    P. Xue, P. Chen, J. Jia, Q. Xu, J. Sun, B. Yao, Z. Zhang, R. Lu, Chem. Commun. 50, 2569 (2014)CrossRefGoogle Scholar
  9. 9.
    W.Z. Yuan, Y. Tan, Y. Gong, P. Lu, J.W.Y. Lam, X.Y. Shen, C. Feng, H.H.-Y. Sung, Y. Lu, I.D. Williams, J.Z. Sun, Y. Zhang, B.Z. Tang, Adv. Mater. 25, 2837 (2013)CrossRefGoogle Scholar
  10. 10.
    B. Xu, Y. Mu, Z. Mao, Z. Xie, H. Wu, Y. Zhang, C. Jin, Z. Chi, S. Liu, J. Xu, Y.-C. Wu, P.-Y. Lu, A. Lien, M.R. Bryce, Chem. Sci. 7, 2201 (2016)CrossRefGoogle Scholar
  11. 11.
    C. Arivazhagan, A. Maity, K. Bakthavachalam, A. Jana, S.K. Panigrahi, E. Suresh, A. Das, S. Ghosh, Chem. Eur. J. 23, 1 (2017)CrossRefGoogle Scholar
  12. 12.
    G. Yin, Y. Ma, Y. Xiong, X. Cao, Y. Li, L. Chen, J. Mater. Chem. C 4, 751 (2016)CrossRefGoogle Scholar
  13. 13.
    Y. Wang, D. Xu, H. Gao, Y. Wang, X. Liu, A. Han, C. Zhang, L. Zang, J. Phys. Chem. C 122, 2297 (2018)CrossRefGoogle Scholar
  14. 14.
    Z. Chi, X. Zhang, B. Xu, X. Zhou, C. Ma, Y. Zhang, S. Liu, J. Xu, Chem. Soc. Rev. 41, 3878 (2012)CrossRefGoogle Scholar
  15. 15.
    Y. Cao, L. Chen, Y. Xi, Y. Li, X. Yan, Mater. Lett. 212, 225 (2018)CrossRefGoogle Scholar
  16. 16.
    Y. Cao, Y. Xi, X.Y. Teng, Y. Li, X. Yan, L. Chen, Dyes Pigments 137, 75 (2017)CrossRefGoogle Scholar
  17. 17.
    Y. Cao, L. Chen, D. Liu, B. Wang, Sci. China Mater. (2018).  https://doi.org/10.1007/s40843-018-9371-y CrossRefGoogle Scholar
  18. 18.
    D. Karthik, K.R.J. Thomas, J.-H. Jou, Y.-L. Chen, Dyes Pigments 133, 132 (2016)CrossRefGoogle Scholar
  19. 19.
    Z. Li, Z. Li, C. Di, Z. Zhu, Q. Li, Q. Zeng, K. Zhang, Y. Liu, C. Ye, Z.J. Qin, Macromolecules 39, 6951 (2006)CrossRefGoogle Scholar
  20. 20.
    P. Xue, J. Sun, P. Chen, P. Wang, B. Yao, P. Gong, Z. Zhang, R. Lu, Chem. Commun. 51, 10381 (2015)CrossRefGoogle Scholar
  21. 21.
    L. Chen, Y. Jiang, H. Nie, R. Hu, H.S. Kwok, F. Huang, A. Qin, Z. Zhao, B.Z. Tang, ACS Appl. Mater. Interfaces 6, 17215 (2014)CrossRefGoogle Scholar
  22. 22.
    E. Horak, M. Robić, A. Šimanović, V. Mandić, R. Vianello, M. Hranjec, I.M. Steinberg, Dyes Pigments 162, 688 (2019)CrossRefGoogle Scholar
  23. 23.
    X. Zhang, X. Huang, X. Gan, Z. Wu, J. Yu, H. Zhou, Y. Tian, J. Wu, Sens. Actuators B 243, 421 (2017)CrossRefGoogle Scholar
  24. 24.
    H. Zhu, J. Huang, L. Kong, Y. Tian, J. Yang, Dyes Pigments 151, 140 (2018)CrossRefGoogle Scholar
  25. 25.
    R. Hu, E. Lager, A.A. Aguilar, J. Liu, J.W.Y. Lam, H.H.Y. Sung, I.D. Williams, Y. Zhong, K.S. Wong, E.P. Cabrera, B.Z. Tang, J. Phys. Chem. C 113, 15845 (2009)CrossRefGoogle Scholar
  26. 26.
    A. Kundu, S. Karthikeyan, D. Moon, S.P. Anthony, ChemistrySelect 3, 7340 (2018)CrossRefGoogle Scholar
  27. 27.
    Y. Zhan, P. Gong, P. Yang, Z. Jin, Y. Bao, Y. Lia, Y. Xu, RSC Adv. 6, 32697 (2016)CrossRefGoogle Scholar
  28. 28.
    J. Wu, Y. Cheng, J. Lan, D. Wu, S. Qian, L. Yan, Z. He, X. Li, K. Wang, B. Zou, J. You, J. Am. Chem. Soc. 138, 12803 (2016)CrossRefGoogle Scholar
  29. 29.
    J. Hu, J. Wang, R. Liu, Y. Li, J. Lu, H. Zhu, Dyes Pigments 153, 84 (2018)CrossRefGoogle Scholar
  30. 30.
    C. Ma, X. Zhang, L. Yang, Y. Li, H. Liu, Y. Yang, G. Xie, Y.-C. Ou, Y. Wei, Dyes Pigments 136, 85 (2017)CrossRefGoogle Scholar
  31. 31.
    P.S. Hariharan, D. Moon, S.P. Anthony, CrystEngComm 19, 6489 (2017)CrossRefGoogle Scholar
  32. 32.
    L. Zang, H. Shang, D. Wei, S. Jiang, Sens. Actuators B 185, 389 (2013)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.School of Chemical Engineering and TechnologyTianjin UniversityTianjinPeople’s Republic of China
  2. 2.Collaborative Innovation Center of Chemical Science and EngineeringTianjinPeople’s Republic of China
  3. 3.Tianjin Engineering Research Center of Functional Fine ChemicalsTianjinPeople’s Republic of China

Personalised recommendations