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3,4,5-Triphenyl-1,2,4-triazole-based multifunctional n-type AIEgen

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Abstract

The luminogens with aggregation-induced emission (AIEgens) characteristics have been widely applied in diverse areas. However, the n-type AIEgens are to be further developed. In this paper, we designed and synthesized an n-type multifunctional AIEgen of tetraphenylethene-substituted 3,4,5-triphenyl-4H-1,2,4-triazole (BTPE-TAZ). This AIEgen can serve as both light-emitting and electron-transporting layers in organic light-emitting devices. Moreover, it also exhibits the interesting optical waveguide and reversible mechanochromic luminescence properties, which are of great potential for practical applications.

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References

  1. Tang CW, Van Slyke SA. Appl Phys Lett, 1987, 51: 913–915

    Article  CAS  Google Scholar 

  2. Tang CW, Van Slyke SA, Chen CH. J Appl Phys, 1989, 65: 3610–3616

    Article  CAS  Google Scholar 

  3. Burroughes JH, Bradley DDC, Brown AR, Marks RN, Mackay K, Friend RH, Burns PL, Holmes AB. Nature, 1990, 347: 539–541

    Article  CAS  Google Scholar 

  4. Schouwink P, Schäfer AH, Seidel C, Fuchs H. Thin Solid Films, 2000, 372: 163–168

    Article  CAS  Google Scholar 

  5. Kwon TW, Alam MM, Jenekhe SA. Chem Mater, 2004, 16: 4657–4666

    Article  CAS  Google Scholar 

  6. Luo J, Xie Z, Lam JWY, Cheng L, Tang BZ, Chen H, Qiu C, Kwok HS, Zhan X, Liu Y, Zhu D. Chem Commun, 2001, 1740–1741

    Google Scholar 

  7. Hong Y, Lam JWY, Tang BZ. Chem Commun, 2009, 4332–4353

    Google Scholar 

  8. Liu J, Lam JWY, Tang BZ. J Inorg Organomet Polym, 2009, 19: 249–285

    Article  CAS  Google Scholar 

  9. Liu Y, Tang Y, Barashkov NN, Irgibaeva IS, Lam JWY, Hu R, Birimzhanova D, Yu Y, Tang BZ. J Am Chem Soc, 2010, 132: 13951–13953

    Article  CAS  Google Scholar 

  10. Wang ZT, Fang Y, Sun JZ, Qin AJ, Tang BZ. Sci China Chem, 2013, 56: 1187–1190

    Article  CAS  Google Scholar 

  11. Chen M, Li L, Nie H, Tong J, Yan L, Xu B, Sun JZ, Tian W, Zhao Z, Qin A, Tang BZ. Chem Sci, 2015, 6: 1932–1937

    Article  CAS  Google Scholar 

  12. Tao S, Li L, Yu J, Jiang Y, Zhou Y, Lee CS, Lee ST, Zhang X, Kwon O. Chem Mater, 2009, 21: 1284–1287

    Article  CAS  Google Scholar 

  13. Liu Y, Chen S, Lam JWY, Lu P, Kwok RTK, Mahtab F, Kwok HS, Tang BZ. Chem Mater, 2011, 23: 2536–2544

    Article  CAS  Google Scholar 

  14. Yang J, Li L, Yu Y, Ren Z, Peng Q, Ye S, Li Q, Li Z. Mater Chem Front, 2017, 1: 91–99

    Article  Google Scholar 

  15. 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: 89–94

    Article  CAS  Google Scholar 

  16. Li L, Nie H, Chen M, Sun J, Qin A, Tang BZ. Faraday Discuss, 2017, doi: 10.1039/C6FD00163G

    Google Scholar 

  17. Yuan WZ, Lu P, Chen S, Lam JWY, Wang Z, Liu Y, Kwok HS, Ma Y, Tang BZ. Adv Mater, 2010, 22: 2159–2163

    Article  CAS  Google Scholar 

  18. Qin W, Liu J, Chen S, Lam JWY, Arseneault M, Yang Z, Zhao Q, Kwok HS, Tang BZ. J Mater Chem C, 2014, 2: 3756–3761

    Article  CAS  Google Scholar 

  19. Kim K, Lee DW, Jin JI. Synth Met, 2000, 114: 49–56

    Article  CAS  Google Scholar 

  20. Anderson JD, McDonald EM, Lee PA, Anderson ML, Ritchie EL, Hall HK, Hopkins T, Mash EA, Wang J, Padias A, Thayumanavan S, Barlow S, Marder SR, Jabbour GE, Shaheen S, Kippelen B, Peyghambarian N, Wightman RM, Armstrong NR. J Am Chem Soc, 1998, 120: 9646–9655

    Article  CAS  Google Scholar 

  21. Huang J, Yang X, Li X, Chen P, Tang R, Li F, Lu P, Ma Y, Wang L, Qin J, Li Q, Li Z. Chem Commun, 2012, 48: 9586–9588

    Article  CAS  Google Scholar 

  22. Kido J, Ohtaki C, Hongawa H, Okuyama K, Nagai K. Jpn J Appl Phys, 1993, 32: L917–L920

    Article  CAS  Google Scholar 

  23. Shih HT, Lin CH, Shih HH, Cheng CH. Adv Mater, 2002, 14: 1409–1412

    Article  CAS  Google Scholar 

  24. Yamamoto T, Maruyama T, Zhou ZH, Ito T, Fukuda T, Yoneda Y, Begum F, Ikeda T, Sasaki S. J Am Chem Soc, 1994, 116: 4832–4845

    Article  CAS  Google Scholar 

  25. Agrawal AK, Jenekhe SA. Macromolecules, 1993, 26: 895–905

    Article  CAS  Google Scholar 

  26. Tonzola CJ, Alam MM, Kaminsky W, Jenekhe SA. J Am Chem Soc, 2003, 125: 13548–13558

    Article  CAS  Google Scholar 

  27. Kulkarni AP, Tonzola CJ, Babel A, Jenekhe SA. Chem Mater, 2004, 16: 4556–4573

    Article  CAS  Google Scholar 

  28. Li ZH, Wong MS, Fukutani H, Tao Y. Org Lett, 2006, 8: 4271–4274

    Article  CAS  Google Scholar 

  29. Feng XJ, Wu PL, Li KF, Wong MS, Cheah KW. Chem Eur J, 2011, 17: 2518–2526

    Article  CAS  Google Scholar 

  30. Wu CS, Chen Y. J Mater Chem, 2010, 20: 7700–7709

    Article  CAS  Google Scholar 

  31. Weder C. J Mater Chem, 2011, 21: 8235–8236b

    Article  CAS  Google Scholar 

  32. Zhang G, Lu J, Sabat M, Fraser CL. J Am Chem Soc, 2010, 132: 2160–2162

    Article  CAS  Google Scholar 

  33. Li K, Liu B. Chem Soc Rev, 2014, 43: 6570–6597d

    Article  CAS  Google Scholar 

  34. He J, Xu B, Chen F, Xia H, Li K, Ye L, Tian W. J Phys Chem C, 2009, 113: 9892–9899

    Article  CAS  Google Scholar 

  35. Fang C, Xie Y, Johnston MR, Ruan Y, Tang BZ, Peng Q, Tang Y. J Phys Chem A, 2015, 119: 8049–8054

    Article  CAS  Google Scholar 

  36. Li Q, Li Z. Sci China Chem, 2015, 58: 1800–1809

    Article  CAS  Google Scholar 

  37. Shen XY, Wang YJ, Zhao E, Yuan WZ, Liu Y, Lu P, Qin A, Ma Y, Sun JZ, Tang BZ. J Phys Chem C, 2013, 117: 7334–7347

    Article  CAS  Google Scholar 

  38. Kawano T, Yoshizumi T, Hirano K, Satoh T, Miura M. Org Lett, 2009, 11: 3072–3075

    Article  CAS  Google Scholar 

  39. Mei J, Hong Y, Lam JWY, Qin A, Tang Y, Tang BZ. Adv Mater, 2014, 26: 5429–5479

    Article  CAS  Google Scholar 

  40. Chen J, Law CCW, Lam JWY, Dong Y, Lo SMF, Williams ID, Zhu D, Tang BZ. Chem Mater, 2003, 15: 1535–1546

    Article  CAS  Google Scholar 

  41. Deng SL, Chen TL, Chien WL, Hong JL. J Mater Chem C, 2014, 2: 651–659

    Article  CAS  Google Scholar 

  42. Jin YJ, Kim H, Kim JJ, Heo NH, Shin JW, Teraguchi M, Kaneko T, Aoki T, Kwak G. Cryst Growth Des, 2016, 16: 2804–2809

    Article  CAS  Google Scholar 

  43. Yang Z, Qin W, Leung NLC, Arseneault M, Lam JWY, Liang G, Sung HHY, Williams ID, Tang BZ. J Mater Chem C, 2016, 4: 99–107

    Article  CAS  Google Scholar 

  44. Zhang GF, Chen ZQ, Aldred MP, Hu Z, Chen T, Huang Z, Meng X, Zhu MQ. Chem Commun, 2014, 50: 12058–12060

    Article  CAS  Google Scholar 

  45. Qin A, Lam JWY, Mahtab F, Jim CKW, Tang L, Sun J, Sung HHY, Williams ID, Tang BZ. Appl Phys Lett, 2009, 94: 253308

    Article  Google Scholar 

  46. Mei J, Wang J, Sun JZ, Zhao H, Yuan W, Deng C, Chen S, Sung HHY, Lu P, Qin A, Kwok HS, Ma Y, Williams ID, Tang BZ. Chem Sci, 2012, 3: 549–558

    Article  CAS  Google Scholar 

  47. Gu X, Yao J, Zhang G, Yan Y, Zhang C, Peng Q, Liao Q, Wu Y, Xu Z, Zhao Y, Fu H, Zhang D. Adv Funct Mater, 2012, 22: 4862–4872

    Article  CAS  Google Scholar 

  48. Heng L, Wang X, Tian D, Zhai J, Tang B, Jiang L. Adv Mater, 2010, 22: 4716–4720

    Article  CAS  Google Scholar 

  49. Wang E, Lam JWY, Hu R, Zhang C, Zhao YS, Tang BZ. J Mater Chem C, 2014, 2: 1801–1807

    Article  CAS  Google Scholar 

  50. Zhao N, Li M, Yan Y, Lam JWY, Zhang YL, Zhao YS, Wong KS, Tang BZ. J Mater Chem C, 2013, 1: 4640–4646b

    Article  CAS  Google Scholar 

  51. Morris WA, Butler T, Kolpaczynska M, Fraser CL. Mater Chem Front, 2017, 1: 158–166

    Article  Google Scholar 

  52. Chi Z, Zhang X, Xu B, Zhou X, Ma C, Zhang Y, Liu S, Xu J. Chem Soc Rev, 2012, 41: 3878–3896

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the key project of the Ministry of Science and Technology of China (2013CB834702), the National Natural Science Foundation of China (21525417), the Natural Science Foundation of Guangdong Province (2016A030312002), the National Program for Support of Top-Notch Young Professionals, the Fundamental Research Funds for the Central Universities (2015ZY013) and the Innovation and Technology Commission (ITC-CNERC14S01). YJ Cai thanks China Postdoctoral Science Foundation Grant (2016M602463). AJ Qin and BZ Tang thank the support from Guangdong Innovative Research Team Program (201101C0105067115).

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Authors and Affiliations

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

    Yang Shi, Yi Jia Wang, Ming Chen, Haoke Zhang, Jing Zhi Sun, Anjun Qin & Ben Zhong Tang

  2. Guangdong Innovative Research Team, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640, China

    Yuanjing Cai, Han Nie, Anjun Qin & Ben Zhong Tang

  3. Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong, China

    Wei Qin & Ben Zhong Tang

Authors
  1. Yang Shi
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  2. Yuanjing Cai
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  3. Yi Jia Wang
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  4. Ming Chen
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  5. Han Nie
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  6. Wei Qin
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  7. Haoke Zhang
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  8. Jing Zhi Sun
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  9. Anjun Qin
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  10. Ben Zhong Tang
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Corresponding authors

Correspondence to Anjun Qin or Ben Zhong Tang.

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These authors contribute equally to this work.

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Shi, Y., Cai, Y., Wang, Y.J. et al. 3,4,5-Triphenyl-1,2,4-triazole-based multifunctional n-type AIEgen. Sci. China Chem. 60, 635–641 (2017). https://doi.org/10.1007/s11426-016-0433-x

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  • DOI: https://doi.org/10.1007/s11426-016-0433-x

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