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


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.


Pyrone Mechanofluorochromic Solvatochromism Blue-shifted 


Supplementary material

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


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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

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