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Synthesis and host-guest properties of pillar[6]arenes

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Abstract

A facile method for the synthesis of pillar[6]arenes was developed. A series of pillar[6]arenes were prepared with FeCl3 as catalyst and chloroform as solvent at room temperature in moderate yields (30%–40%). Their host-guest properties with n-cetyltrimethyl ammonium bromide were investigated by 1 HNMR. The results showed that high selectivity in the host-guest relationship became apparent between pillar[6]arenes and pillar[5]arenes based on the different size of the inner cavity.

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References

  1. Gale PA, Anzenbacher P, Sessler JL. Calixpyrroles II. Coord Chem Rev, 2001, 222: 57–102

    Article  CAS  Google Scholar 

  2. Morohashi N, Narumi F, Iki N, Hattori T, Miyano S. Thiacalixarenes. Chem Rev, 2006, 106: 5291–5316

    Article  CAS  Google Scholar 

  3. Zhu XZ, Chen CF. A highly efficient approach to [4]pseudocatenanes by threefold metathesis reactions of a triptycene-based tris[2]pseu-dorotaxane. J Am Chem Soc, 2005, 127: 13158–13159

    Article  CAS  Google Scholar 

  4. Ananchenko GS, Moudrakovski IL, Coleman AW, Ripmeester JA. A channel-free soft-walled capsular calixarene solid for gas adsorption. Angew Chem Int Ed, 2008, 47: 5616–5618

    Article  CAS  Google Scholar 

  5. Han T, Zong QS, Chen CF. Complexation of triptycene-based cylindrical macrotricyclic polyether toward diquaternary salts: Ion-controlled binding and release of the guests. J Org Chem, 2007, 72: 3108–3111

    Article  CAS  Google Scholar 

  6. Zheng YS, Zhang C. Exceptional chiral recognition of racemic carboxylic acids by chiral calix[4]arenas bearing optical pure amino alcohol groups at low rim. Org Lett, 2004, 6: 1189–1192

    Article  CAS  Google Scholar 

  7. Ogoshi T, Kanai S, Fujinami S, Yamagishi T, Nakamoto Y. Para-bridged symmetrical pillar[5]arenes: Their lewis acid catalyzed synthesis and host-guest property. J Am Chem Soc, 2008, 130: 5022–5023.

    Article  CAS  Google Scholar 

  8. Cao DR, Kou YH, Liang JQ, Chen ZZ, Wang LY, Meier H. A facile and efficient preparation of pillararenes and a pillarquinone. Angew Chem Int Ed, 2009, 48: 9721–9723

    CAS  Google Scholar 

  9. Han CY, Zhang ZB, Xia BY, Yu YH, Huang FH. DIBPillar[n]arenes (n = 5, 6): Syntheses, X-ray crystal structures, and complexation with n-octyltriethyl ammonium hexafluorophosphate. Org Lett, 2010, 19: 4360–4365

    Article  Google Scholar 

  10. Li CJ, Zhao L, Li J, Ding X, Chen SH, Zhang QL, Yu YH, Jia XS. Self-assembly of [2]pseudorotaxanes based on pillar[5]arene and bis(imidazolium) cations. Chem Commun, 2010, 46: 9016–9018

    Article  CAS  Google Scholar 

  11. Zhang ZB, Xia BY, Han CY, Yu YH, Huang FH. Syntheses of copil lar[5]arenes by co-oligomerization of different monomers. Org Lett, 2010, 12: 3285–3287

    Article  CAS  Google Scholar 

  12. Kou YH, Tao HQ, Cao DR, Fu ZY, Schollmeyer D, Meier H. Synthesis and conformational properties of nonsymmetric pillar[5]arenes and their acetonitrile inclusion compounds. Eur J Org Chem, 2010, 33: 6464–6470

    Article  Google Scholar 

  13. Ogoshi T, Aoki T, Kitajima K, Fujinami S, Yamagishi T, Nakamoto Y. Facile, rapid, and high-yield synthesis of pillar[5]arene from commercially available reagents and its X-ray crystal Structure. J Org Chem, 2011, 76: 328–331

    Article  CAS  Google Scholar 

  14. Bolm C, Legros J, Le PJ, Zani L. Iron-catalyzed reactions in organic synthesis. Chem Rev, 2004, 104: 6217–6254

    Article  CAS  Google Scholar 

  15. Komeyama K, Morimoto T, Takaki K. A simple and efficient iron-catalyzed intramolecular hydroamination of unactivated olefins. Angew Chem Int Ed, 2006, 45: 2938–2941

    Article  CAS  Google Scholar 

  16. Jian HH, Tour JM. Preparative fluorous mixture synthesis of diazonium-functionalized oligo(phenylene vinylene)s. J Org Chem, 2005, 70: 3396–3424

    Article  CAS  Google Scholar 

  17. Fang Z, Wang S, Zhao L, Xu Z, Ren J, Wang X, Yang Q. Synthesis and characterization of blue light emitting materials containing imidazole. Mater Chem Phys, 2008, 107: 305–309

    Article  CAS  Google Scholar 

  18. Li YT, Zhu YP, Meng XG, Wu AX. Solvent effect on pseudopolymorphism of hemicyclohexylcucurbit[6]uril. Crys Grow Des, 2009, 4255–4257

  19. Alberts B, Johnson A, Lewis J, Raff M, Roberts K, Walter P, Mol Biol. Cell Garland Science. 4th ed, Taylor & Francis Group: New York. 2002, 134

    Google Scholar 

  20. Du M, Zhao XJ, Guo JH, Batten SR. Direction of topological isomers of silver(I) coordination polymers induced by solvent, and selective anion-exchange of a class of PtS-type host frameworks. Chem Commun, 2005, 4836–4838

  21. Chen SF, Yu SH, Yu B, Ren L, Yao WT, Colfen H, Solvent effect on mineral modification: Selective synthesis of cerium compounds by a facile solution route. Chem Eur J, 2004, 10: 3050–3058

    Article  CAS  Google Scholar 

  22. Schnatwinkel B, Stoll I, Mix A, Rekharsky MV, Borovkov VV, Inoue Y, Mattay J. Monomeric, dimeric and hexameric resorcin[4] arene assemblies with alcoholsin apolar solvents. Chem Commun, 2008, 3873–3875

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, China

    HongQi Tao, DeRong Cao, LuZhi Liu, YuHui Kou & LingYun Wang

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

    DeRong Cao

  3. Institute of Organic Chemistry, University of Mainz, 55099, Mainz, Germany

    Herbert Meier

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  1. HongQi Tao
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  2. DeRong Cao
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  3. LuZhi Liu
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  4. YuHui Kou
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  5. LingYun Wang
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  6. Herbert Meier
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Correspondence to DeRong Cao.

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Tao, H., Cao, D., Liu, L. et al. Synthesis and host-guest properties of pillar[6]arenes. Sci. China Chem. 55, 223–228 (2012). https://doi.org/10.1007/s11426-011-4427-3

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  • DOI: https://doi.org/10.1007/s11426-011-4427-3

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