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A novel Route to Synthesize p-Terphenyl from Benzene by the Catalysis of h-BN Nanoparticles

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Abstract

We have investigated the catalytic effect of boron nitride (h-BN) nanoparticles. The experiments prove that p-terphenyl can be synthesized from benzene at 400 °C in the presence of h-BN nanoparticles, thereby implying that the observed catalytic property of the h-BN nanoparticles may expand the application field of inorganic nanocrystals. The paper also discusses the mechanism of the structural rearrangement and oligomerization from benzene to p-terphenyl.

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References

  1. B.M. Trost, Science 254, 1471 (1991)

    Article  CAS  Google Scholar 

  2. B.M. Trost, Angew. Chem. Int. Ed. 34, 259 (1995)

    Article  CAS  Google Scholar 

  3. C.B. Murray, C.R. Kagan, M.G. Bawendi, Science 270, 1335 (1995)

    Article  CAS  Google Scholar 

  4. W.P. Halperin, Rev. Mod. Phys. 58, 1453 (1986)

    Article  Google Scholar 

  5. W.Y. Choi, Angew. Chem. Int. Ed. 33, 1091 (1994)

    Article  Google Scholar 

  6. Y.G. Lou, M.M. Maye, L. Han, J. Luo, C.J. Zhong, Chem. Comm. 5, 473 (2001)

    Article  Google Scholar 

  7. G. Schmid, M. Bäumle, M. Geerkens, I. Heim, C. Osemann, T. Sawitowski, Chem. Soc. Rev. 28, 179 (1999)

    Article  CAS  Google Scholar 

  8. H. Yoneyama, Crit. Rev. Solid State Mater. Sci. 18, 69 (1993)

    Article  CAS  Google Scholar 

  9. V. Sukharev, A. Wold, Y.M. Gao, K. Dwight, J. Solid State Chem. 119, 339 (1995)

    Article  CAS  Google Scholar 

  10. L.Q. Xu, J.H. Zhan, J.Q. Hu, Y. Bando, X.L. Yuan, T. Sekiguchi, M. Mitome, D. Golberg, Adv. Mater. 19, 2141 (2007)

    Article  CAS  Google Scholar 

  11. C.C. Tang, Y. Bando, Y. Huang, C.Y. Zhi, D. Golberg, Adv. Funct. Mater. 18, 3653 (2008)

    Article  CAS  Google Scholar 

  12. J.B. Lian, T. Kim, X.D. Liu, J.M. Ma, W.J. Zheng, J. Phys. Chem. C 113, 9135 (2009)

    Article  CAS  Google Scholar 

  13. G. Lian, X. Zhang, L.L. Zhu, M. Tan, D.L. Cui, Q.L. Wang, J. Mater. Chem. 20, 3736 (2010)

    Article  CAS  Google Scholar 

  14. T.W. Hansen, J.B. Wagner, P.L. Hansen, S. Dahl, H. Topsøe, Claus J.H. Jacobsen, Science 294, 1508 (2001)

    Article  CAS  Google Scholar 

  15. A. Ishikawa, M. Neurock, E. Iglesia, J. Am. Chem. Soc. 129, 13201 (2007)

    Article  CAS  Google Scholar 

  16. T.H. Chiang, T.E. Hsieh, J. Inorg. Organomet. Polym. 16, 175 (2006)

    Article  CAS  Google Scholar 

  17. M.M. Fan, E.N. Duesler, J.F. Janik, R.T. Paine, J. Inorg. Organomet. Polym. 17, 423 (2007)

    Article  CAS  Google Scholar 

  18. F. Maya, J.M. Tour, Tetrahedron 60, 81 (2004)

    Article  CAS  Google Scholar 

  19. I. Yamaguchi, K. Goto, M. Sato, Tetrahedron 65, 3645 (2009)

    Article  CAS  Google Scholar 

  20. F. Hide, M.A. Diaz-Garcia, B.J. Schwartz, A.J. Heeger, Acc. Chem. Res. 30, 430 (1997)

    Article  CAS  Google Scholar 

  21. G. Yu, J. Gao, J.C. Hummelen, F. Wudl, A.J. Heeger, Science 270, 1789 (1995)

    Article  CAS  Google Scholar 

  22. P. Bordat, R. Brown, Chem. Phys. Lett. 331, 439 (2000)

    Article  CAS  Google Scholar 

  23. R.T. Arnold, C. Collins, W. Zenk, J. Am. Chem. Soc. 62, 983 (1940)

    Article  CAS  Google Scholar 

  24. B.K. Ganguly, S.M. Mukherji, Nature 168, 1003 (1951)

    Article  CAS  Google Scholar 

  25. L.A. Adrio, J.M.A. Míguez, K.K. Hii, Org. Prep. Proced. Int. 41, 331 (2009)

    Article  CAS  Google Scholar 

  26. W. Liu, H. Cao, A.W. Lei, Angew. Chem. Int. Ed. 49, 2004 (2010)

    CAS  Google Scholar 

  27. W. Liu, H. Cao, H. Zhang, H. Zhang, K.H. Chung, C. He, H.B. Wang, F.Y. Kwong, A.W. Lei, J. Am. Chem. Soc. 132, 16737 (2010)

    Article  CAS  Google Scholar 

  28. H.J. Jo, C.B. Kim, T.Y. Ryoo, B.K. Ahn, K.Y. Park, Bull. Korean Chem. Soc. 31, 3749 (2010)

    Article  CAS  Google Scholar 

  29. H. Tanaka, A. Kosaka, S. Yamashita, K. Morisaki, S. Torii, Tetrahedron Lett. 30, 1261 (1989)

    Article  CAS  Google Scholar 

  30. A. Goel, D. Verma, F.V. Singh, Tetrahedron Lett. 46, 8487 (2005)

    Article  CAS  Google Scholar 

  31. X.P. Hao, D.L. Cui, X.Q. Yu, Z.G. Liu, X.G. Xu, Q.L. Wang, M.H. Jiang, Mater. Lett. 57, 703 (2002)

    Article  CAS  Google Scholar 

  32. C.X. Lu, H.G. Du, Oranic Chemistry (Science Press, Beijing, 2003)

    Google Scholar 

  33. X.P. Hao, D.L. Cui, G.X. Shi, Y.Q. Yin, X.G. Xu, M.H. Jiang, X.W. Xu, Y.P. Li, Mater. Lett. 51, 509 (2001)

    Article  CAS  Google Scholar 

  34. J. Hilton, Sadtler Standard Infrared Grating Spectra 1–2, 1–2000 (1974)

    Google Scholar 

  35. C.H. Cho, I.S. Kim, K.Y. Park, Tetrahedron 60, 4589 (2004)

    Article  CAS  Google Scholar 

  36. H. Du, R.A. Fuh, J. Li, A. Corkan, J.S. Lindsey, Photochem. Photobiol. 68, 141 (1998)

    CAS  Google Scholar 

  37. L.D. Zhang, J.M. Mou, Nanomaterials and nanostructure (Science Press, Beijing, 2001)

    Google Scholar 

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Acknowledgment

This work was financially supported by NSFC (Contract No. 50801042), National Basic Research Program of China (2011CB301904, 2009CB930503), the Fund for the Natural Science of Shandong Province (ZR2010EM020, ZR2010EM049) and IIFSDU (2009TS041).

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Correspondence to Yongzhong Wu.

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Li, H., Wu, Y. & Xu, X. A novel Route to Synthesize p-Terphenyl from Benzene by the Catalysis of h-BN Nanoparticles. J Inorg Organomet Polym 21, 827–831 (2011). https://doi.org/10.1007/s10904-011-9559-6

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