Citation: Xiao-Shi Hu, Hong-Mei Deng, Jian Li, Xue-Shun Jia, Chun-Ju Li. Selective binding of unsaturated aliphatic hydrocarbons by a pillar[5]arene[J]. Chinese Chemical Letters, ;2013, 24(8): 707-709. shu

Selective binding of unsaturated aliphatic hydrocarbons by a pillar[5]arene

1.
Department of Chemistry, Shanghai University, Shanghai 200444, China

Corresponding author: Chun-Ju Li,
Received Date: 28 February 2013
Available Online: 23 April 2013

The complexation behavior of unsaturated fatty hydrocarbons, i.e., 1,7-octadiyne and 1,7-octadiene, by a perethylated pillar[5]arene has been investigated, which was compared with that for saturated n-octane. It was found that the host-guest binding strength increased in accordance with the electron-negativity of the terminal carbon atom on the guests: alkyne > alkene > alkane.
- Molecular recognition,
- Pillararenes,
- Unsaturated hydrocarbons,
- Supramolecular chemistry
1. [1]
  [1] (a) A. Harada, A. Hashidzume, H. Yamaguchi, Y. Takashima, Polymeric rotaxanes, Chem. Rev. 109 (2009) 5974-6023;
2. [2]
  (b) Y. Chen, Y. Liu, Cyclodextrin-based bioactive supramolecular assemblies, Chem. Soc. Rev. 39 (2010) 495-505;
3. [3]
  (c) G. Chen, M. Jiang, Cyclodextrin-based inclusion complexation bridging supramolecular chemistry and macromolecular self-assembly, Chem. Soc. Rev. 40 (2011) 2254-2266;
4. [4]
  (d) H. Tian, Q.C. Wang, Recent progress on switchable rotaxanes, Chem. Soc. Rev. 35 (2006) 361-374;
5. [5]
  (e) D.R. Patil, D.S. Dalal, Biomimetic approach for the synthesis of N,N'-diarylsubstituted formamidines catalysed by b-cyclodextrin in water, Chin. Chem. Lett. 23 (2012) 1125-1128;
6. [6]
  (f) S.A. Nepogodiev, J.F. Stoddart, Cyclodextrin-based catenanes and rotaxanes, Chem. Rev. 98 (1998) 1959-1976.
7. [7]
  [2] (a) P.R. Ashton, D. Philp, N. Spencer, J.F. Stoddart, The self-assembly of [n]pseudorotaxanes, J. Chem. Soc. Chem. Commun. (1991) 1677-1679;
8. [8]
  (b) S.J. Loeb, J.A. Wisner, A new motif for the self-assembly of [2]pseudorotaxanes; 1,2-bis(pyridinium)ethane axles and [24]crown-8 ether wheels, Angew. Chem. Int. Ed. 37 (1998) 2838-2840;
9. [9]
  (c) B. Zheng, M. Zhang, S. Dong, J. Liu, F. Huang, A benzo-21-crown-7/secondary ammonium salt [c2]daisy chain, Org. Lett. 14 (2012) 306-309;
10. [10]
  (d) P.D. Beer, M.R. Sambrook, D. Curiel, Anion-templated assembly of interpenetrated and interlocked structures, Chem. Commun. (2006) 2105-2117;
11. [11]
  (e) Z. Niu, H.W. Gibson, Polycatenanes, Chem. Rev. 109 (2009) 6024-6046;
12. [12]
  (f) M. Zhang, K. Zhu, F.Huang, Improved complexation of paraquat derivatives by the formation of crown ether-based cryptands, Chem. Commun. 46 (2010) 8131-8141;
13. [13]
  (g) C.F. Chen, Novel triptycene-derived hosts: synthesis and their applications in supramolecular chemistry, Chem. Commun. 47 (2011) 1674-1688;
14. [14]
  (h) Z.J. Zhang, H.Y. Zhang, H. Wang, Y. Liu, A twin-axial hetero[7]rotaxane, Angew. Chem. Int. Ed. 50 (2011) 10834-10838.
15. [15]
  [3] (a) V. Böhmer, Calixarenes, macrocycles with (almost) unlimited possibilities, Angew. Chem. Int. Ed. Engl. 34 (1995) 713-745;
16. [16]
  (b) A. Ikeda, S. Shinkai, Novel cavity design using calix[n]arene skeletons: toward molecular recognition and metal binding, Chem. Rev. 97 (1997) 1713-1734;
17. [17]
  (c) S.J. Dalgarno, P.K. Thallapally, L.J. Barbour, J.L. Atwood, Engineering void space in organic van der Waals crystals: calixarenes lead the way, Chem. Soc. Rev. 36 (2007) 236-245;
18. [18]
  (d) D.M. Homden, C. Redshaw, The use of calixarenes in metal-based catalysis, Chem. Rev. 108 (2008) 5086-5130;
19. [19]
  (e) X.Y. Ling, D.N. Reinhoudt, J. Huskens, From supramolecular chemistry to nanotechnology: assembly of 3D nanostructures, Pure Appl. Chem. 81 (2009) 2225-2233;
20. [20]
  (f) S.M. Biros, J. Rebek, Structure and binding properties of water-soluble cavitands and capsules, J. Chem. Soc. Rev. 36 (2007) 93-104;
21. [21]
  (g) D.S. Guo, V.D. Uzunova, X. Su, Y. Liu, W.M. Nau, Operational calixarene-based fluorescent sensing systems for choline and acetylcholine and their application to enzymatic reactions, Chem. Sci. 2 (2012) 1722-1734;
22. [22]
  (h) M.X. Wang, Nitrogen and oxygen bridged calixaromatics: synthesis, structure, functionalization, and molecular recognition, Acc. Chem. Res. 45 (2012) 182-195.
23. [23]
  [4] (a) S. Gadde, A.E. Kaifer, Cucurbituril complexes of redox active guests, Curr. Org. Chem. 15 (2011) 27-38;
24. [24]
  (b) L. Isaacs, Cucurbit[n]urils: from mechanism to structure and function, Chem. Commun. (2009) 619-629;
25. [25]
  (c) K. Kim, N. Selvapalam, Y.H. Ko, et al., Functionalized cucurbiturils and their applications, Chem. Soc. Rev. 36 (2007) 267-279;
26. [26]
  (d) H. Qian, D.S. Guo, Y. Liu, Cucurbituril-modulated supramolecular assemblies: from cyclic oligomer to linear polymer, Chem. Eur. J. 18 (2012) 5087-5095;
27. [27]
  (e) J. Lagona, P. Mukhopadhyay, S. Chakrabarti, L. Isaacs, The cucurbit[n]uril family, Angew. Chem. Int. Ed. 44 (2005) 4844-4870.
28. [28]
  [5] (a) T. Ogoshi, S. Kanai, S. Fujinami, T. Yamagishi, Y. Nakamoto, Para-bridged symmetrical pillar[5]arenes: their lewis acid catalyzed synthesis and host-guest property, J. Am. Chem. Soc. 130 (2008) 5022-5023;
29. [29]
  (b) N.L. Strutt, R.S. Forgan, J.M. Spruell, Y.Y. Botros, J.F. Stoddart, Monofunctionalized pillar[5]arene as a host for alkanediamines, J. Am. Chem. Soc. 133 (2011) 5668-5671;
30. [30]
  (c) D. Cao, Y. Kou, J. Liang, Z. Chen, L. Wang, H. Meier, A facile and efficient preparation of pillararenes and a pillarquinone, Angew. Chem. Int. Ed. 48 (2009) 9721-9723;
31. [31]
  (d) Z. Zhang, Y. Luo, J. Chen, et al., Formation of linear supramolecular polymers that is driven by C-H p interactions in solution and in the solid state, Angew. Chem. Int. Ed. 50 (2011) 1397-1401;
32. [32]
  (e) X.B. Hu, L. Chen, W. Si, Y. Yu, J.L. Hou, Pillar[5]arene decaamine: synthesis, encapsulation of very long linear diacids and formation of ion pair-stopped[2]rotaxanes, Chem. Commun. 47 (2011) 4694-4696;
33. [33]
  (f) Y. Ma, X. Chi, X. Yan, et al., per-Hydroxylated pillar[6]arene: synthesis, X-ray crystal structure, and host-guest complexation, Org. Lett. 14 (2012) 1532-1535.
34. [34]
  [6] (a) Z. Zhang, B. Xia, C. Han, Y. Yu, F. Huang, Syntheses of copillar[5]arenes by cooligomerization of different monomers, Org. Lett. 12 (2010) 3285-3287;
35. [35]
  (b) Z. Zhang, Y. Luo, B. Xia, et al., Four constitutional isomers of BMpillar[5]arene: synthesis, crystal structures and complexation with n-octyltrimethyl ammonium hexafluorophosphate, Chem. Commun. 47 (2011) 2417-2419;
36. [36]
  (c) C. Li, Q. Xu, J. Li, F. Yao, X. Jia, Complex interactions of pillar[5]arene with paraquats and bis(pyridinium) derivatives, Org. Biomol. Chem. 8 (2010) 1568-1576;
37. [37]
  (d) C. Li, L. Zhao, J. Li, et al., Self-assembly of [2]pseudorotaxanes based on pillar[5]arene and bis(imidazolium) cations, Chem. Commun. 46 (2010) 9016-9018;
38. [38]
  (e) K. Wang, L.L. Tan, D.X. Chen, et al., One-pot synthesis of pillar[n]arenes catalyzed by a minimum amount of TfOH and a solution-phase mechanistic study, Org. Biomol. Chem. 10 (2012) 9405-9409;
39. [39]
  (f) H. Zhang, X. Ma, J. Guo, et al., Thermo-responsive fluorescent vesicles assembled by fluorescein-functionalized pillar[5]arene, RSC Adv. 3 (2013) 368-371;
40. [40]
  (g) W. Si, L. Chen, X.B. Hu, et al., Selective artificial transmembrane channels for protons by formation of water wires, Angew. Chem. Int. Ed. 50 (2011) 12564-12568;
41. [41]
  (h) Q. Duan, W. Xia, X. Hu, et al., Novel [2]pseudorotaxanes constructed by selfassembly of bis-urea-functionalized pillar[5]arene and linear alkyl dicarboxylates, Chem. Commun. 48 (2012) 8532-8534.
42. [42]
  [7] (a) C. Li, S. Chen, J. Li, et al., Novel neutral guest recognition and interpenetrated complex formation from pillar[5]arenes, Chem. Commun. 47 (2011) 11294-11296;
43. [43]
  (b) C. Li, K. Han, J. Li, et al., Synthesis of pillar[5]arene dimers and their cooperative binding toward some neutral guests, Org. Lett. 14 (2012) 42-45;
44. [44]
  (c) X. Shu, S. Chen, J. Li, et al., Highly effective binding of neutral dinitriles by simple pillar[5]arenes, Chem. Commun. 48 (2012) 2967-2969.
45. [45]
  [8] Y. Inoue, K. Yamamoto, T. Wada, et al., Inclusion complexation of (cyclo)alkanes and (cyclo)alkanols with 6-O-modified cyclodextrins, J. Chem. Soc. Perkin Trans. 2 (1998) 1807-1816.
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