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New tetraphenylpyridinium-based luminogens with aggregation-induced emission characteristics

  • Communications
  • Special Topic Aggregated-Induced Emission
  • Published:
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Abstract

The research on aggregation-induced emission (AIE) has drawn increasing interests in the past decade. With the efforts scientists paid, a variety of AIE systems have been developed, among which the tetraphenylethelene and silole derivatives are the most studied. Development of new AIE systems could further enrich the AIE molecules and promote the development of AIE area. In this communication, we prepared a new AIE system based on 1,2,4,6-tetraphenylpyridinium ions according to the restriction of intramolecular rotation mechanism. These molecules could be facilely synthesized via one-step and one-pot reaction. The ionic AIE-active molecules could find wide application in sensing and optoelectronic areas.

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References

  1. Shimizu M, Hiyama T. Organic fluorophores exhibiting highly efficient photoluminescence in the solid state. Chem Asian J, 2010, 5: 1516–1531

    Article  CAS  Google Scholar 

  2. Liu B, Dan T, Bazan GC. Collective response from a cationic tetrahedral fluorene for label-free DNA detection. Adv Funct Mater, 2007, 17: 2432–2438

    Article  CAS  Google Scholar 

  3. Chen Q, Wang JX, Yang F, Zhou D, Bian N, Zhang XJ, Yan CG, Han BH. Tetraphenylethylene-based fluorescent porous organic polymers: Preparation, gas sorption properties and photoluminescence properties. J Mater Chem, 2011, 21: 13554–13560

    Article  CAS  Google Scholar 

  4. Chi ZG, Zhang XQ, Xu BJ, Zhou X, Ma CP, Zhang Y, Liu SW, Xu JR. Recent advances in organic mechanofluorochromic materials. Chem Soc Rev, 2012, 41: 3878–3896

    Article  CAS  Google Scholar 

  5. Ning ZJ, Chen Z, Zhang Q, Yan YL, Qian SX, Cao Y, Tian H. Aggregation-induced emission (AIE)-active starburst triarylamine fluorophores as potential non-doped red emitters for organic light-emitting diodes and Cl2 gas chemodosimeter. Adv Funct Mater, 2007, 17: 3799–3807

    Article  CAS  Google Scholar 

  6. Teng MJ, Jia XR, Yang S, Chen XF, Wei Y. Reversible tuning luminescent color and emission intensity: a dipeptide-based light-emitting material. Adv Mater, 2012, 24: 1255–1261

    Article  CAS  Google Scholar 

  7. Lee SH, Jang BB, Kafafi ZH. Highly fluorescent solid-state asymmetric spirosilabifluorene derivatives. J Am Chem Soc, 2005, 127: 9071–9078

    Article  CAS  Google Scholar 

  8. Aldred MP, Li C, Zhang GF, Gong WL, Li ADQ, Dai YF, Ma DG, Zhu MQ. Fluorescence quenching and enhancement of vitrifiable oligofluorenes end-capped with tetraphenylethene. J Mater Chem, 2012, 22: 7515–7528

    Article  CAS  Google Scholar 

  9. Wang J, Zhao Y, Dou YC, Sun H, Xu P, Ye K, Zhang J, Jing S, Li F, Wang Y. Alkyl and dendron substituted quinacridones: Synthesis, structures, and luminescent properties. J Phys Chem B, 2007, 111: 5082–5089

    Article  CAS  Google Scholar 

  10. Hecht S, Fréchet JMJ. Dendritic encapsulation of function: Applying nature’s site isolation principle from biomimetics to materials science. Angew Chem Int Ed, 2001, 40: 74–91

    Article  CAS  Google Scholar 

  11. Chen L, Xu S, McBranch D, Whitten D. Tuning the properties of conjugated polyelectrolytes through surfactant complexation. J Am Chem Soc, 2000, 122: 9302–9303

    Article  CAS  Google Scholar 

  12. Hong YN, Lam JWY, Tang BZ. Aggregation-induced emission. Chem Soc Rev, 2011, 40: 5361–5388

    Article  CAS  Google Scholar 

  13. Hong YN, Lam JWY, Tang BZ. Aggregation-induced emission: Phenomenon, mechanism and application. Chem Commun, 2009, 4332–4353

  14. Qin AJ, Lam JWY, Tang BZ. Luminogenic polymers with aggregation-induced emission characteristics. Prog Polym Sci, 2012, 37: 182–209

    Article  CAS  Google Scholar 

  15. Luo JD, Xie ZL, Lam JWY, Cheng L, Chen HY, Qiu CF, Kwok HS, Zhan XW, Liu YQ, Zhu DB, Tang BZ. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem Commun, 2001, 1740–1741

  16. Chen JW, Law CCW, Lam JWY, Dong YP, Lo SMF, Williams ID, Zhu DB, Tang BZ. Synthesis, light emission, nanoaggregation, and restricted intramolecular rotation of 1,1-substituted 2,3,4,5-tetraphenylsiloles. Chem Mater, 2003, 15:1535–1546

    Article  CAS  Google Scholar 

  17. Zhang S, Qin AJ, Sun JZ, Tang BZ. Progress in mechanism study of aggregation-induced emission. Prog Chem, 2011, 23:623–636

    CAS  Google Scholar 

  18. Li Z, Dong YQ, Mi BX, Tang YH, Haussler M, Tong H, Dong YP, Lam JWY, Ren Y, Sung HHY, Wong KS, Gao P, Williams ID, Kwok HS, Tang BZ. Structural control of the photoluminescence of silole regioisomers and their utility as sensitive regiodiscriminating chemosensors and efficient electroluminescent materials. J Phys Chem B, 2005, 109:10061–10069

    Article  CAS  Google Scholar 

  19. Zeng Q, Li Z, Dong YQ, Di CA, Qin AJ, Hong YN, Ji L, Zhu ZC, Jim CKW, Yu G, Li QQ, Li ZA, Liu YQ, Qin JG, Tang BZ. Fluores cence enhancements of benzene-cored luminophores by restricted intramolecular rotations: AIE and AIEE effects. Chem Commun, 2007, 70-72

  20. Shi JQ, Chang N, Li CH, Mei J, Deng CM, Luo XL, Liu ZP, Bo ZS, Dong YQ, Tang BZ. Locking the phenyl rings of tetraphenylethene step by step: understanding the mechanism of aggregation-induced emission. Chem Commun, 2012, 48: 10675–10677

    Article  CAS  Google Scholar 

  21. Li Y, Zhou NC, Zhang W, Zhang F, Zhu J, Zhang ZB, Cheng ZP, Tu YF, Zhu XL. Light-driven and aggregation-induced emission from side-chain azoindazole polymers. J Polym Sci Part A: Polym Chem, 2011, 49: 4911–4920

    Article  CAS  Google Scholar 

  22. Yao H, Ashiba K. Highly fluorescent organic nanoparticles of thiacyanine dye: A synergetic effect of intermolecular H-aggregation and restricted intramolecular rotation. RSC Adv, 2011, 1: 834–838

    Article  CAS  Google Scholar 

  23. Chien WL, Yang CM, Chen TL, Li ST, Hong JL. Enhanced emission of a pyridine-based luminogen by hydrogen-bonding to organic and polymeric phenols. RSC Adv 2013, 3: 6930–6938

    Article  CAS  Google Scholar 

  24. Wu QY, Deng CM, Peng Q, Niu YL, Shuai ZG. Quantum chemical insights into the aggregation induced emission phenomena: A QM/MM study for pyrazine derivatives. J Comput Chem, 2012, 33: 1862–1869

    Article  CAS  Google Scholar 

  25. He JT, Xu B, Chen FP, Xia HJ, Li KP, Ye L, Tian WJ. Aggregation-induced emission in the crystals of 9,10-distyrylanthracene derivatives: The essential role of restricted intramolecular torsion. J Phys Chem C, 2009, 113: 9892–9899

    Article  CAS  Google Scholar 

  26. Qian LJ, Zhi JG, Tong B, Yang F, Zhao W, Dong YP. Organic compounds with aggregation-induced emission. Prog Chem, 2008, 20: 673–678

    CAS  Google Scholar 

  27. Zhao GS, Shi CX, Guo ZQ, Zhu WH, Zhu SQ. Recent application progress on aggregation-induced emission. Chin J Org Chem, 2012, 32: 1620–1632

    Article  CAS  Google Scholar 

  28. Wang M, Zhang GX, Zhang DQ, Zhu DB, Tang BZ. Fluorescent bio/chemosensors based on silole and tetraphenylethene luminogens with aggregation-induced emission feature. J Mater Chem, 2010, 20: 1858–1867

    Article  CAS  Google Scholar 

  29. Ding D, Li K, Liu B, Tang BZ. Bioprobes based on AIE fluorogens. Acc Chem Res, 2013, 46: DOI: 10.1021/ar3003464

    Google Scholar 

  30. Miranda MA, Garcia H. 2,4,6-Triphenylpyrylium tetrafluoroborate as an electron-transfer photosensitizer. Chem Rev, 1994, 94, 1063–1089

    Google Scholar 

  31. Perez RT, Sanchez-Pedreno C, Ortuno JA. 1,2,4,6-Tetraphenylpyri-dinium perchlorate as a reagent for ion-association complex formation and its use for the spectrophotometric determination of thallium. Analyst, 1982, 107: 185–189

    Article  Google Scholar 

  32. Han FL, Lu Y, Zhang Q, Sun JF, Zeng XS, Li CX. Homogeneous and sensitive DNA detection based on polyelectrolyte complexes of cationic conjugated poly(pyridinium salt)s and DNA. J Mater Chem, 2012, 22: 4106–4112

    Article  CAS  Google Scholar 

  33. Fortage J, Tuyèras F, Ochsenbein P, Puntoriero F, Nastas F, Campagna S, Griveau S, Bedioui F, Ciofini I, Lainé PP. Expanded pyridiniums biscyclization of branched pyridiniums into their fused polycyclic and positively charged derivatives-assessing the impact of pericondensation on structural, electrochemical, electronic, and photophysical feature, Chem Eur J, 2010, 16: 11047–1063

    Article  CAS  Google Scholar 

  34. Wang J, Mei J, Hu RR, Sun JZ, Qin AJ, Tang BZ. Click synthesis, aggregation-induced emission, E/Z isomerization, self-organization, and multiple chromisms of pure stereoisomers of a tetraphenyl-ethene-cored luminogen. J Am Chem Soc, 2012, 134: 9956–9966

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, 310027, China

    ZongTan Wang, Yuan Fang, JingZhi Sun, AnJun Qin & Ben Zhong Tang

  2. Department of Chemistry, Institute for Advanced Study, Institute of Molecular Functional Materials, The Hong Kong University of Science & Technology (HKUST), Clear Water Bay, Kowloon, Hong Kong, China

    Ben Zhong Tang

  3. Guangdong Innovative Research Team, SCUT-HKUST Joint Research Laboratory, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology (SCUT), Guangzhou, 510640, China

    Ben Zhong Tang

Authors
  1. ZongTan Wang
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  2. Yuan Fang
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  3. JingZhi Sun
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  4. AnJun Qin
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  5. Ben Zhong Tang
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Correspondence to AnJun Qin or Ben Zhong Tang.

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Wang, Z., Fang, Y., Sun, J. et al. New tetraphenylpyridinium-based luminogens with aggregation-induced emission characteristics. Sci. China Chem. 56, 1187–1190 (2013). https://doi.org/10.1007/s11426-013-4933-6

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  • DOI: https://doi.org/10.1007/s11426-013-4933-6

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