Citation: Huang Guo-Bao, Liu Wei-Er, Valkonen Arto, Yao Huan, Rissanen Kari, Jiang Wei. Selective recognition of aromatic hydrocarbons by endo-functionalized molecular tubes via C/N-H… π interactions[J]. Chinese Chemical Letters, ;2018, 29(1): 91-94. doi: 10.1016/j.cclet.2017.07.005 shu

Selective recognition of aromatic hydrocarbons by endo-functionalized molecular tubes via C/N-H… π interactions

  • Corresponding author: Jiang Wei, jiangw@sustc.edu.cn
  • Received Date: 15 May 2017
    Revised Date: 14 June 2017
    Accepted Date: 4 July 2017
    Available Online: 5 January 2017

Figures(6)

  • Molecular recognition of aromatic hydrocarbons by four endo-functionalized molecular tubes has been studied by 1H NMR spectroscopy, computational methods, and single crystal X-ray crystallography. The binding selectivity is rationalized by invoking shape complementarity and dipole alignment. The noncovalent interactions are proved to predominantly be C/N-H…π interactions.
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    1. [1]

      (a) P. A. Gale, J. W. Steed, Supramolecular Chemistry: From Molecules to Nanomaterials (Molecular Recognition), vol. 3, Wiley, Chichester, 2012;
      (b) J. Rebek Jr., Angew. Chem. Int. Ed. Engl. 29(1990) 245-255;
      (c) D. Chatterji, Basics of Molecular Recognition, CRC Press, Holland, 2016; (d) Y. C. Pan, H. W. Tian, S. Peng, X. Y. Hu, D. S. Guo, Chin. Chem. Lett. 28(2017) 787-792.

    2. [2]

      (a) T. Heinz, D. M. Rudkevich, J. Rebek Jr., Nature 394(1998) 764-766;
      (b) W. Jiang, J. Rebek Jr., J. Am. Chem. Soc. 134(2012) 17498-17501.

    3. [3]

      R. G. Harvey, Polycyclic Aromatic Hydrocarbons, Wiley-VCH, New York, 1997.

    4. [4]

      (a) A. K. Haritash, C. P. Kaushik, J. Hazard. Mater. 169(2009) 1-15;
      (b) C. E. Bostrom, P. Gerde, A. Hanberg, et al., Environ. Health Perspect. 110(2002) 451-488.

    5. [5]

      (a) M. S. Khoshbin, M. V. Ovchinnikov, K. S. Salaita, et al., Chem. Asian J. 1(2006) 686-692;
      (b) Y. R. Zheng, Z. Zhao, M. Wang, et al., J. Am. Chem. Soc. 132(2010) 16873-16882;
      (c) T. Nakamura, H. Ube, M. Shionoya, Angew. Chem. Int. Ed. 125(2013) 748-751.

    6. [6]

      (a) E. J. Dale, N. A. Vermeulen, M. Jurícek, et al., Acc. Chem. Res. 49(2016) 2629-273;
      (b) J. C. Barnes, M. Jurícek, N. L. Strutt, et al., J. Am. Chem. Soc. 135(2013) 1839-192;
      (c) E. J. Dale, N. A. Vermeulen, A. A. Thomas, et al., J. Am. Chem. Soc. 136(2014) 10669-10682.

    7. [7]

      (a) P. Spenst, F. Würthner, Angew. Chem. Int. Ed. 127(2015) 10303-10306;
      (b) P. Spenst, A. Sieblist, F. Würthner, Chem. Eur. J. 23(2017) 1667-1675;
      (c) P. Spenst, R. M. Young, B. T. Phelan, et al., J. Am. Chem. Soc. 139(2017) 2014-2021.

    8. [8]

      (a) E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. Int. Ed. 42(2003) 1210-1250;
      (b) L. M. Salonen, M. Ellermann, F. Diederich, Angew. Chem. Int. Ed. 50(2011) 4808-4842.

    9. [9]

      M. Nishio, M. Hirota, Y. Umezawa, The CH/p Interaction: Evidence, Nature, and Consequences, Wiley-VCH, Canada, 1998.

    10. [10]

      (a) S. K. Burley, G. A. Petsko, Science 229(1985) 23-28;
      (b) S. K. Burley, G. A. Petsko, J. Am. Chem. Soc. 108(1986) 7995-8001.

    11. [11]

      Z. He, X. Yang, W. Jiang, Org. Lett. 17(2015) 3880-3883.  doi: 10.1021/acs.orglett.5b01871

    12. [12]

      (a) Z. He, G. Ye, W. Jiang, Chem. Eur. J. 21(2015) 3005-3012;
      (b) G. B. Huang, W. Jiang, Prog. Chem. 27(2015) 744-754;
      (c) H. Yao, L. P. Yang, Z. F. He, et al., Chin. Chem. Lett. 28(2017) 782-786;
      (d) H. Yao, J. N. Sun, H. Ke, et al., Chin. J. Org. Chem. 37(2017) 603-607.

    13. [13]

      (a) F. Jia, Z. He, L. P. Yang, et al., Chem. Sci. 6(2015) 6731-6738;
      (b) F. Jia, H. Y. Wang, D. H. Li, et al., Chem. Commun. 52(2016) 5666-5669;
      (c) F. Jia, D. H. Li, T. L. Yang, et al., Chem. Commun. 53(2017) 336-339;
      (d) L. P. Yang, W. E. Liu, W. Jiang, Tetrahedron Lett. 57(2016) 3978-3985;
      (e) G. B. Huang, S. H. Wang, H. Ke, et al., J. Am. Chem. Soc. 138(2016) 14550-14553;
      (f) L. P. Yang, F. Jia, Q. H. Zhou, et al., Chem. Eur. J. 23(2017) 1516-1520;
      (g) L. P. Yang, H. Liu, S. B. Lu, et al., Org. Lett. 19(2017) 1212-1215;
      (h) L. L. Wang, Z. Chen, W. E. Liu, et al., J. Am. Chem. Soc. 139(2017) 8436-8439.

    14. [14]

      (a) G. Huang, Z. He, C. X. Cai, et al., Chem. Commun. 51(2015) 15490-15493;
      (b) G. Huang, A. Valkonen, K. Rissanen, W. Jiang, Chem. Commun. 52(2016) 9078-9081;
      (c) D. N. Lande, M. N. Shewale, S. P. Gejji, J. Phys. Chem. A (2017), doi: http://dx.doi.org/10.1021/acs.jpca.7b02238.

    15. [15]

      S. Wang, Y. Wang, Z. Chen, et al., Chem. Commun. 51(2015) 3434-3437.  doi: 10.1039/C4CC08820D

    16. [16]

      (a) K. Hirose, Determination of binding constants, in: C. A. Shalley (Ed. ), Analytical Methods in Supramolecular Chemsitry, Wiley-VCH, Weinheim, 2007, pp. 17-54;
      (b) K. Hirose, J. Incl. Phenom. Macrocycl. Chem. 39(2001) 193-209.

    17. [17]

      P. Thordarson, Chem. Soc. Rev. 42(2011) 1305-1323.

    18. [18]

      R.W. Taft, F.G. Bordwell, Acc. Chem. Res. 21(1988) 463-469.  doi: 10.1021/ar00156a005

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