Science China Materials

, Volume 62, Issue 6, pp 823–830 | Cite as

Multi-responsive red solid emitter: Detection of trace water and sense of relative humidity

  • Yuqi Cao (曹宇奇)
  • Ligong Chen (陈立功)Email author
  • Dongqi Liu (刘东琦)
  • Bowei Wang (王博威)Email author


A multi-responsive D-A type compound (CYQ) based on pyrone and triphenylamine was designed and successfully synthesized. The target compound exhibited distinct aggregation-enhanced emission (AEE) effect. Solvatochromic experiment and density functional theory (DFT) indicated CYQ possessed excellent intramolecular charge transfer (ICT) ability. Besides, its mechanofluorochromic property (MFC) was found with a 37 nm redshift. Powder wide-angle X-ray diffraction (PXRD) and differential scanning calorimetry (DSC) measurements were performed to demonstrate the transformation from the crystalline to amorphous states upon grinding. Surprisingly, CYQ displayed a hypersensitive response to trace water in organic solvents with an excellent detection limit as low as 0.0096% in tetrahydrofuran (THF). Furthermore, it was found that the fluorescent intensity of CYQ declined progressively upon humidity rise, and its color change can be witnessed by naked eyes. Therefore, the relative humidity (RH) sensing strategy guarantees the AIEgen to become a colorimetric sensor under various conditions.


aggregation-enhanced emission mechanofluorochromic trace water humidity 

刺激响应红色发光体: 痕量水及相对湿度的检测


本文设计并开发了一种以吡喃酮和三苯胺为母体的多刺激响应D-A型化合物(CYQ). 目标产物表现出优异的聚集诱导发光增强性能(AEE). 溶剂变色实验及密度泛函理论表明CYQ具有极强的分子内电荷转移(ICT)性质. 粉末广角X射线衍射(PXRD)及差式扫描量热法(DSC)证明了在外力作用下, 分子由晶态向无定型态的转变. 研究发现, CYQ对有机溶液中的痕量水非常敏感, 在四氢呋喃(THF)中可达到极低的检出限0.0096%. 除此之外, 随着湿度的增加, CYQ的荧光强度呈现逐渐下降趋势. 这一相对湿度检测法为该AIE材料成为不同环境下的比色探针提供了可能.



We are grateful for the financial support from the National Natural Science Foundation of China (21576194).

Supplementary material

40843_2018_9371_MOESM1_ESM.pdf (347 kb)
Multi-responsive red solid emitter: Detection of trace water and Sense of relative humidity


  1. 1.
    Liu J, Chen C, Ji S, et al. Long wavelength excitable near-infrared fluorescent nanoparticles with aggregation-induced emission characteristics for image-guided tumor resection. Chem Sci, 2017, 8: 2782–2789CrossRefGoogle Scholar
  2. 2.
    Song F, Xu Z, Zhang Q, et al. Highly efficient circularly polarized electroluminescence from aggregation-induced emission luminogens with amplified chirality and delayed fluorescence. Adv Funct Mater, 2018, 28: 1800051–1800063CrossRefGoogle Scholar
  3. 3.
    Chen S, Liu J, Liu Y, et al. An AIE-active hemicyanine fluorogen with stimuli-responsive red/blue emission: extending the pH sensing range by “switch + knob” effect. Chem Sci, 2012, 3: 1804–1809CrossRefGoogle Scholar
  4. 4.
    Shi P, Duan Y, Wei W, et al. A turn-on type mechanochromic fluorescent material based on defect-induced emission: implication for pressure sensing and mechanical printing. J Mater Chem C, 2018, 6: 2476–2482CrossRefGoogle Scholar
  5. 5.
    Luo J, Xie Z, Lam JWY, et al. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem Commun, 2001, 1740–1741Google Scholar
  6. 6.
    Wang B, Chen P, Zhang J, et al. Self-assembled core–shell-corona multifunctional non-viral vector with AIE property for efficient hepatocyte-targeting gene delivery. Polym Chem, 2017, 8: 7486–7498CrossRefGoogle Scholar
  7. 7.
    Zhu H, Huang J, Kong L, et al. Branched triphenylamine luminophores: Aggregation-induced fluorescence emission, and tunable near-infrared solid-state fluorescence characteristics via external mechanical stimuli. Dyes Pigments, 2018, 151: 140–148CrossRefGoogle Scholar
  8. 8.
    Liu D, Li J, Liu J, et al. A new organic compound of 2-(2,2-diphenylethenyl) anthracene (DPEA) showing simultaneous electrical charge transport property and AIE optical characteristics. J Mater Chem C, 2018, 6: 3856–3860CrossRefGoogle Scholar
  9. 9.
    Xia Q, Chen Z, Yu Z, et al. Aggregation-induced emission-active near-infrared fluorescent organic nanoparticles for noninvasive long-term monitoring of tumor growth. ACS Appl Mater Interfaces, 2018, 10: 17081–17088CrossRefGoogle Scholar
  10. 10.
    Wang D, Zhao H, Li H, et al. A fluorescent “glue” of water triggered by hydrogen-bonding cross-linking. J Mater Chem C, 2016, 4: 11050–11054CrossRefGoogle Scholar
  11. 11.
    Wang L, Yang L, Li L, et al. The synthesis and highly sensitive detection of water content in THF using a novel solvatochromic AIE polymer containing diketopyrrolopyrrole and triphenylamine. New J Chem, 2016, 40: 6706–6713CrossRefGoogle Scholar
  12. 12.
    Liu Y, Lei Y, Li F, et al. Indene-1,3-dionemethylene-4H-pyran derivatives containing alkoxy chains of various lengths: aggregation-induced emission enhancement, mechanofluorochromic properties and solvent-induced emission changes. J Mater Chem C, 2016, 4: 2862–2870CrossRefGoogle Scholar
  13. 13.
    Hancock JM, Gifford AP, Zhu Y, et al. n-Type conjugated oligoquinoline and oligoquinoxaline with triphenylamine endgroups: efficient ambipolar light emitters for device applications. Chem Mater, 2006, 18: 4924–4932CrossRefGoogle Scholar
  14. 14.
    Lin Y, Chen G, Zhao L, et al. Diethylamino functionalized tetraphenylethenes: structural and electronic modulation of photophysical properties, implication for the CIE mechanism and application to cell imaging. J Mater Chem C, 2015, 3: 112–120CrossRefGoogle Scholar
  15. 15.
    Zhao L, Lin Y, Liu T, et al. Rational bridging affording luminogen with AIE features and high field effect mobility. J Mater Chem C, 2015, 3: 4903–4909CrossRefGoogle Scholar
  16. 16.
    Venkatramaiah N, Kumar GD, Chandrasekaran Y, et al. Efficient blue and yellow organic light-emitting diodes enabled by aggregation-induced emission. ACS Appl Mater Interfaces, 2018, 10: 3838–3847CrossRefGoogle Scholar
  17. 17.
    Cao YQ, Xi Y, Teng XY, et al. Alkoxy substituted D-p-A dimethyl-4-pyrone derivatives: Aggregation induced emission enhancement, mechanochromic and solvatochromic properties. Dyes Pigments, 2017, 137: 75–83CrossRefGoogle Scholar
  18. 18.
    Guan XL, Jia TM, Zhang DH, et al. A new solvatochromic linear p-conjugated dye based on phenylene-(poly)ethynylene as supersensitive low-level water detector in organic solvents. Dyes Pigments, 2017, 136: 873–880CrossRefGoogle Scholar
  19. 19.
    Yuan WZ, Gong Y, Chen S, et al. Efficient solid emitters with aggregation-induced emission and intramolecular charge transfer characteristics: molecular design, synthesis, photophysical behaviors, and OLED application. Chem Mater, 2012, 24: 1518–1528CrossRefGoogle Scholar
  20. 20.
    Cao YQ, Chen L, Xi Y, et al. Stimuli-responsive 2,6-diarylethene-4H-pyran-4-one derivatives: Aggregation induced emission enhancement, mechanochromism and solvatochromism. Mater Lett, 2018, 212: 225–230CrossRefGoogle Scholar
  21. 21.
    Gao H, Xu D, Wang Y, et al. Effects of alkyl chain length on aggregation-induced emißsion, self-assembly and mechanofluorochromism of tetraphenylethene modified multifunctional β-diketonate boron complexes. Dyes Pigments, 2018, 150: 59–66CrossRefGoogle Scholar
  22. 22.
    Bu L, Li Y, Wang J, et al. Synthesis and piezochromic luminescence of aggregation-enhanced emission 9,10-bis(N-alkylcarbazol-2-yl-vinyl-2)anthracenes. Dyes Pigments, 2013, 99: 833–838CrossRefGoogle Scholar

Copyright information

© Science China Press and Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  • Yuqi Cao (曹宇奇)
    • 1
    • 2
  • Ligong Chen (陈立功)
    • 1
    • 2
    • 3
    Email author
  • Dongqi Liu (刘东琦)
    • 1
    • 2
  • Bowei Wang (王博威)
    • 1
    • 2
    • 3
    Email author
  1. 1.School of Chemical Engineering and TechnologyTianjin UniversityTianjinChina
  2. 2.Collaborative Innovation Center of Chemical Science and Engineering (Tianjin)TianjinChina
  3. 3.Tianjin Engineering Research Center of Functional Fine ChemicalsTianjinChina

Personalised recommendations