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Synthesis and luminescence properties of long-chain (2,7-carbazolyl)-adamantane copolymers

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Abstract

Several long-chain (2,7-carbazolyl) adamantane copolymers, with molecular weight ranging from 4500 to 6000, were synthesized by palladium-catalyzed Suzuki reaction using 1,5-bis (4-bromophenyl) adamantane and N-(2-ethylhexyl)-2,7-carbazole as building molecules. The copolymers were characterized by infrared, ultraviolet, nuclear magnetic resonance (NMR), fluorescence spectroscopies, and thermal analysis. It was found that the introduction of adamantyl group into the backbone of conjugated carbazole polymer significantly improves the thermal stability and spectral stability of the copolymer. These copolymers giving high color purity showed excellent comprehensive performance: the thermal decomposition temperature is up to 409 ~ 432 °C, glass-transition temperature is about 83 ~ 162 °C, fluorescence quantum efficiency is as high as 0.76 ~ 0.85. Hence, the synthesized copolymers have great potential for being used as new blue-light-emitting materials.

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References

  1. Tang W, Lin T, Ke L, Chen Z (2008) Synthesis, photophysics, theoretical modeling, and electroluminescence of novel 2,7-carbazole-based conjugated polymers with sterically hindered structures J Polym Sci A Polym Chem 46(23):7725–7738. doi:10.1002/pola.23076

    Article  CAS  Google Scholar 

  2. Blouin N, Leclerc M (2008) Poly(2,7-carbazole)s: structure-property relationships Acc Chem Res 41(9):1110–1119. doi:10.1021/ar800057k

    Article  CAS  Google Scholar 

  3. Hattori Y, Miyajima T, Sakai M, Nagase Y, Nemoto N (2008) Synthesis and thermal characterization of novel adamantane-based polysiloxane Polymer 49(12):2825–2831. doi:10.1016/j.polymer.2008.04.053

    Article  CAS  Google Scholar 

  4. Gu Y, Zhu L, Li Y, Yu L, Wu K, Chen T, Huang M, Wang F, Gong S, Ma D (2015) Adamantane-based wide-Bandgap host material: blue Electrophosphorescence with high efficiency and very high brightness Chem Eur J 21(22):8250–8256

    Article  CAS  Google Scholar 

  5. Gu Y, Zhou X, Li Y, Wu K, Wang F, Huang M, Guo F, Wang Y, Gong S, Ma D (2015) Tetrasubstituted adamantane derivatives with arylamine groups: solution-processable hole-transporting and host materials with high triplet energy and good thermal stability for organic light-emitting devices Org Electron 25:193–199. doi:10.1016/j.orgel.2015.06.036

    Article  CAS  Google Scholar 

  6. Zheng SY, Shi JM, Mateu R (2000) Novel blue light emitting polymer containing an adamantane moiety Chem Mater 12(7):1814. doi:10.1021/cm0002281

    Article  CAS  Google Scholar 

  7. Li J, Hirayama Y, Sano T, Tomita T, Fujii H, Wakisaka K (2006) Reduction of chain interactions in a class of blue fluorene copolymers with adamantane units Thin Solid Films 515(4):2686–2691. doi:10.1016/j.tsf.2006.06.029

    Article  CAS  Google Scholar 

  8. Zhao QJ, Wu WH (2009) Synthesis and photoluminescence properties of thermal-stable polyfluorenes modified with adamantane derivatives as inserted-backbone units or chain ends Synth Met 159(12):1153–1157. doi:10.1016/j.synthmet.2009.01.051

    Article  CAS  Google Scholar 

  9. Li C, Bo Z (2010) Three-dimensional conjugated macromolecules as light-emitting materials Polymer 51(19):4273–4294. doi:10.1016/j.polymer.2010.07.007

    Article  CAS  Google Scholar 

  10. Müllen K, Dierschke F, Grimsdale AC (2003) Efficient synthesis of 2,7-Dibromocarbazoles as components for Electroactive materials Synthesis 16:2470–2472. doi:10.1055/s-2003-42418

    Article  Google Scholar 

  11. Freeman AW, Urvoy M, Criswell ME (2005) Triphenylphosphine-mediated reductive cyclization of 2-nitrobiphenyls: a practical and convenient synthesis of carbazoles J Org Chem 70(13):5014–5019. doi:10.1021/jo0503299

    Article  CAS  Google Scholar 

  12. Dierschke F, Grimsdale AC, Mullen K (2004) Novel carbazole-based ladder-type polymers for electronic applications Macromol Chem Phys 205(9):1147–1154. doi:10.1002/macp.200300219

    Article  CAS  Google Scholar 

  13. Mori S, Takeuchi Y, Tanatani A, Kagechika H, Fujii S (2015) Development of 1,3-diphenyladamantane derivatives as nonsteroidal progesterone receptor antagonists Bioorg Med Chem 23(4):803–809. doi:10.1016/j.bmc.2014.12.047

    Article  CAS  Google Scholar 

  14. Hamai S, Hirayama F (1983) Actinometric determination of absolute fluorescence quantum yields J Phys Chem 87(1):83–89. doi:10.1021/j100224a020

    Article  CAS  Google Scholar 

  15. Zotti G, Schiavon G, Zecchin S, Morin J-F, Leclerc M (2002) Electrochemical, conductive, and magnetic properties of 2,7-Carbazole-based conjugated polymers Macromolecules 35(6):2122–2128. doi:10.1021/ma011311c

    Article  CAS  Google Scholar 

  16. Morin JF, Beaupre S, Leclerc M, Levesque I, D'Iorio M (2002) Blue light-emitting devices from new conjugated poly(N-substituted-2,7-carbazole) derivatives Appl Phys Lett 80(3):341–343. doi:10.1063/1.1433917

    Article  CAS  Google Scholar 

  17. Grell M, Bradley DDC, Ungar G, Hill J, Whitehead KS (1999) Interplay of physical structure and Photophysics for a liquid crystalline Polyfluorene Macromolecules 32(18):5810–5817. doi:10.1021/ma990741o

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors would like to thank the National Natural Science Foundation of China (Grant no.21476051), the Science and Technology Program of Guangdong Province (Grant no. 2016A050502057) and Natural Science Foundation of Guangdong Province (Grant no.2016A030310349). H. Yue is grateful to China Postdoctoral Science Foundation.

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Authors and Affiliations

  1. School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, Guangdong, 510006, China

    Yingchun Liu, Jianwei Guo, Tao Luo, Hangbo Yue, Rilin Tan & Xi Zhao

  2. Department of Biomedicine, Zhongshan Torch Polytechnic, Zhongshan, Guangdong, 528436, China

    Yingchun Liu

  3. Department of Materials Science and Engineering, National Taiwan University of Science and Technology, Taipei, 10607, Taiwan

    Jem Kun Chen

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  1. Yingchun Liu
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  2. Jianwei Guo
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  3. Tao Luo
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  4. Hangbo Yue
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  5. Rilin Tan
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  6. Xi Zhao
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Correspondence to Jianwei Guo.

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Liu, Y., Guo, J., Luo, T. et al. Synthesis and luminescence properties of long-chain (2,7-carbazolyl)-adamantane copolymers. J Polym Res 24, 114 (2017). https://doi.org/10.1007/s10965-017-1265-9

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