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Complexation of two non-fully hydrogen bonded aromatic hydrazide heptamers toward n-octyl-α-L-glucopyranoside in chloroform

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Abstract

Two aromatic hydrazide haptamers have been prepared, with both consisting of two hydrogen bonded folded segments. Compared to their fully hydrogen bonded analogues, the flexibility of their backbones increases due to lack of one or two intramolecular hydrogen bonds at the middle aromatic unit. (2D) 1H NMR, circular dichroism and fluorescent studies revealed that both oligomers moderately complex n-octyl-α-L-glucopyranoside in chloroform.

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References

  1. Pedersen C J. Cyclic polyethers and their complexes with metal salts. J Am Chem Soc, 1967, 89: 2495–2496

    Article  CAS  Google Scholar 

  2. Weber E, Toner J L, Goldberg I, Vögtle F, Laidler D A, Stoddart J F, Bartsch R A, Liotta C L. Crown Ethers and Analogs. Chichester: John Wiley, 1989. 558

    Google Scholar 

  3. Gokel G. W. Crown Ethers and Cryptands. Cambridge: RSC, 1991.

    Google Scholar 

  4. Lehn J M. Supramolecular Chemistry: Concepts and Perspectives. Weinheim: Wiley VCH, 1995. 262

    Google Scholar 

  5. Steed J W, Atwood J L. Supramolecular Chemistry: A Concise Introduction. Chichester: John Wiley, 2000. 400

    Google Scholar 

  6. Vögtle F, Weber E. Multidentate acyclic neutral ligands and their complexation. Angew Chem Int Ed Engl, 1979, 18: 753–776

    Article  Google Scholar 

  7. Hou J L, Shao X B, Chen G J, Zhou Y X, Jiang X K, Li Z T. Hydrogen bonded oligohydrazide foldamers and their recognition for saccharides. J Am Chem Soc, 2004, 126: 12386–12394

    Article  CAS  Google Scholar 

  8. Yi H P, Li C, Hou J L, Jiang X K, Li Z T. Hydrogen-bonding-induced oligoanthranilamide foldamers: Synthesis, characterization, and complexation for alkyl ammonium ions. Tetrahedron, 2005, 61: 7974–7980

    Article  CAS  Google Scholar 

  9. Li C, Ren S F, Hou J L, Yi H P, Zhu S Z, Jiang X K, Li Z T. F⋯H-N Hydrogen bonding driven foldamers: Efficient receptors for dialkylammonium ions. Angew Chem Int Ed, 2005, 44: 5725–5729

    Article  CAS  Google Scholar 

  10. Yi H P, Shao X B, Hou J L, Li C, Jiang X K, Li Z T. Hydrogen-bonding-mediated oligoanthranilamide receptors that efficiently bind a triol and saccharides in chloroform. New J Chem, 2005, 29: 1213–1218

    Article  CAS  Google Scholar 

  11. Li C, Wang G T, Yi H P, Jiang X K, Li Z T, Wang R X. Diastereomeric recognition of chiral foldamer receptors for chiral glucoses. Org Lett, 2007, 9: 1797–1800

    Article  CAS  Google Scholar 

  12. Cai W, Wang G T, Du P, Wang R X, Jiang X K, Li Z T. Foldamer organogels: A circular dichroism study of glucose-mediated dynamic helicity induction and amplification. J Am Chem Soc, 130(40): 13450–13459

  13. Li Z T, Hou J L, Li C, Yi H P. Shape-persistent aromatic amide oligomers: New tools for supramolecular chemistry. Chem Asian J, 2006, 1: 766–778

    Article  CAS  Google Scholar 

  14. Garric J, Leger J M, Huc I. Molecular apple peels. Angew Chem Int Ed, 2005, 44: 1954–1958

    Article  CAS  Google Scholar 

  15. Garric J, Leger J M, Huc I. Encapsulation of small polar guests in molecular apple peels. Chem Eur J, 2007, 13: 8454–8462

    Article  CAS  Google Scholar 

  16. Naito T, Doi E, Miyata O, Ninomiya I. Total synthesis of nuclea alkaloid naucleficine. Heterocycles, 1986, 24: 903–906

    Article  CAS  Google Scholar 

  17. Roosma J, Mes T, Leclere P, Palmans A R A, Meijer E W. Supramolecular materials from benzene-1,3,5-tricarboxamide-based nanorocls. J Am Chem Soc, 2008, 130: 1120–1121

    Article  CAS  Google Scholar 

  18. Gong B. Crescent oligoamides: From acyclic ‘gmacrocycles’ to folding nanotubes. Chem Eur J, 2001, 7: 4337–4342

    Article  Google Scholar 

  19. Huc I. Aromatic oligoamide foldamers. Eur J Org Chem, 2004, 17–29

  20. Conners K A. Binding Constants: The Measurement of Molecular Complex Stability. New York: Wiley, 1987. 432

    Google Scholar 

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Authors and Affiliations

  1. State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China

    Ping Du, YunXiang Xu, XiKui Jiang & ZhanTing Li

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  1. Ping Du
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  2. YunXiang Xu
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  3. XiKui Jiang
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  4. ZhanTing Li
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Correspondence to ZhanTing Li.

Additional information

Supported by the National Natural Science Foundation of China(Grant Nos. 20732007, 20621062, 20872167, and 20672137), the National Basic Research Project (Grant No. 2007CB808000) and the Chinese Academy of Sciences (Grant No. KJCX2-YW-H13)

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Du, P., Xu, Y., Jiang, X. et al. Complexation of two non-fully hydrogen bonded aromatic hydrazide heptamers toward n-octyl-α-L-glucopyranoside in chloroform. Sci. China Ser. B-Chem. 52, 489–496 (2009). https://doi.org/10.1007/s11426-008-0142-0

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  • DOI: https://doi.org/10.1007/s11426-008-0142-0

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