用户名: 密码: 验证码:
Novel β-cyclodextrin-[60]fullerene conjugates based on Huisgen [2+3] cycloaddition: synthesis and dyes complexation properties
详细信息    查看全文
  • 作者:Hongyu Guo ; Xiaoting Fang ; Fafu Yang…
  • 关键词:β ; Cyclodextrin ; [60]fullerene ; Synthesis ; Complexation ; Dye
  • 刊名:Journal of Inclusion Phenomena and Macrocyclic Chemistry
  • 出版年:2016
  • 出版时间:February 2016
  • 年:2016
  • 卷:84
  • 期:1-2
  • 页码:79-86
  • 全文大小:668 KB
  • 参考文献:1.Szejtli, J.: Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98, 1743–1754 (1998)CrossRef
    2.Villalonga, R., Cao, R., Fragoso, A.: Supramolecular chemistry of cyclodextrins in enzyme technology. Chem. Rev. 107, 3088–3116 (2007)CrossRef
    3.Zhou, Y.H., Zhao, M., Mao, Z.W., Ji, L.N.: Ester hydrolysis by a cyclodextrin dimer catalyst with a metallophenanthroline linking group. Chem. Eur. J. 14, 7193–7201 (2008)CrossRef
    4.Zhang, L., Wu, Y., Brunsveld, L.: A synthetic supramolecular construct modulating protein assembly in cells. Angew. Chem. Int. Ed. 46, 1798–1802 (2007)CrossRef
    5.Mura, P.: Analytical techniques for characterization of cyclodextrin complexes in aqueous soluteon: a review. J. Pharm. Biomed. Anal. 101, 238–250 (2014)CrossRef
    6.Sun, T., Guo, Q., Zhang, C., Hao, J., Xing, P., Su, J., Li, S., Hao, A., Liu, G.: Self-assembled vesicles prepared from amphiphilic cyclodextrins as drug carriers. Langmuir 28, 8625–8636 (2012)CrossRef
    7.Ma, M.F., Guan, Y., Zhang, C., Hao, J.C., Xing, P.Y., Su, J., Li, S.Y., Chu, X.X., Hao, A.Y.: Stimulus-responsive supramolecular vesicles with effective anticancer activity prepared by cyclodextrin and ftorafur. Colloids Surf. A 454, 38–45 (2014)CrossRef
    8.Shaikh, M., Swamy, Y.M., Pal, H.: Supramolecular host–guest interaction of acridine dye with cyclodextrin macrocycles: photophysical, pKa shift and quenching study. J. Photochem. Photobiol. A 285, 41–50 (2013)CrossRef
    9.Liu, Y., Kang, S.Z., Zhang, H.Y.: Synthesis of cyclodextrin derivative bearing a cyclohexylamino moiety and its inclusion complexation with organic dye molecules. Microchem. J. 70, 115–121 (2001)CrossRef
    10.Arun, K.T., Jayaram, D.T., Avirah, R.R., Ramaiah, D.: β-Cyclodextrin as a photosensitizer carrier: effect on photophysical properties and chemical reactivity of squaraine dyes. J. Phys. Chem. B 115, 7122–7128 (2011)CrossRef
    11.Liu, Y., Chen, Y.: Cooperative binding and multiple recognition by bridged bis(β-cyclodextrin)s with functional linkers. Acc. Chem. Res. 39, 681–699 (2006)CrossRef
    12.Liu, Y., Li, B., You, C.C., Wada, T., Inoue, Y.: Molecular recognition studies on supramolecular systems. 32. Molecular recognition of dyes by organoselenium
    idged bis(β-cyclodextrin)s. J. Org. Chem. 66, 225–232 (2001)CrossRef
    13.Ikeda, A., Ishikawa, M., Aono, R., Kikuchi, J., Akiyama, M., Shinoda, W.: Regioselective recognition of a [60]fullerene-bisadduct by cyclodextrin. J. Org. Chem. 78, 2534–2541 (2013)CrossRef
    14.Gangadhar, T., Bhoi, V.I., Kumar, B.S., Murthy, C.N.: Supramolecular self-assembly and nanoencapsulation of [60]fullerene by bis-cyclodextrin. J. Incl. Phenom. Macrocycl. Chem. 79, 215–223 (2014)CrossRef
    15.Bhoi, V.I., Kumar, S., Murthy, C.N.: The self-assembly and aqueous solubilization of [60]fullerene with disaccharides. Carbohydr. Res. 359, 120–127 (2012)CrossRef
    16.Bhoi, V.I., Murthy, C.N.: Aqueous solubilization of [60]Fullerene by selectively modified cyclodextrin. Fuller. Nanotubes. Carbon Nanostruct. 19, 668–676 (2011)CrossRef
    17.Wang, J., Zhang, Z., Wu, W., Jiang, X.: Synthesis of β-cyclodextrin-[60]fullerene conjugate and Its DNA cleavage performance. Chin. J. Chem. 32, 78–84 (2014)CrossRef
    18.Rather, J.A., Debnath, P., Wael, K.D.: Fullerene-β-cyclodextrin conjugate based electrochemical sensing device for ultrasensitive detection of p-nitrophenol. Electroanalysis 25, 2145–2150 (2013)CrossRef
    19.Giacalone, F., D’Anna, F., Giacalone, R., Gruttadauria, M., Noto, R.: Cyclodextrin-[60]fullerene conjugates: synthesis, characterization, and electrochemical behavior. Tetrahedron Lett. 47, 8105–8108 (2006)CrossRef
    20.Xiao, S., Wang, Q., Yu, F., Peng, Y., Yang, M., Sollogoub, M., Sinaÿ, P., Zhang, Y., Zahng, L., Zhou, D.: Conjugation of cyclodextrin with fullerene as a new class of HCV entry inhibitors. Bioorg. Med. Chem. 20, 5616–5622 (2012)CrossRef
    21.Zhang, Y.M., Chen, Y., Yang, Y., Liu, P., Liu, Y.: Supramolecular architectures by fullerene
    idged bis(permethyl-bcyclodextrin)s with porphyrins. Chem. Eur. J. 15, 11333–11340 (2009)CrossRef
    22.Guo, H.Y., Yang, F.F., Zhang, Y.M., Di, X.D.: Facile synthesis of mono- and polytopic β-cyclodextrin aromatic aldehydes by click chemistry. Synth. Commun. 3, 338–347 (2015)CrossRef
    23.Yang, F.F., Hong, B.Q., Chai, X.F., Yin, F.J., Chen, Y.Y.: Excellent Ag+ selective receptors: syntheses and complexation properties of novel biscalix[4]arene with benzalazine groups. Supramol. Chem. 21, 691–698 (2009)CrossRef
    24.Connors, K.A.: Binding Constants. Wiley, New York (1987)
    25.Mourer, M., Hapiot, F., Tilloy, S., Monflier, E., Menuel, S.: Easily accessible mono- and polytopic beta-cyclodextrin hosts by click chemistry. Eur. J. Org. Chem. 32, 5723–5730 (2008)CrossRef
    26.Mourer, M., Hapiot, F., Monflier, E.: Click chemistry as an efficient tool to access beta-cyclodextrin dimers. Tetrahedron 64, 7159–7163 (2008)CrossRef
    27.Leung, D.K., Atkins, J.H., Breslow, R.: Synthesis and binding properties of cyclodextrin trimers. Tetrahedron Lett. 42, 6255–6258 (2001)CrossRef
    28.Bushby, R., Hamley, I., Liu, Q., Lozman, O., Lydon, J.: Self-assembled columns of fullerene. J. Mater. Chem. 15, 4429–4435 (2005)CrossRef
    29.Di, X.D., Yang, F.F., Ye, J.Q., Guo, H.Y., Yan, X.Y.: Design, synthesis and properties of novel benzo-15-crown-5/C60 dyads by 1,3-dipolar cycloaddition. Chem. Res. Chin. Univ. 30, 242–244 (2014)CrossRef
  • 作者单位:Hongyu Guo (1)
    Xiaoting Fang (1)
    Fafu Yang (1) (2)
    Yingmei Zhang (1)

    1. College of Chemistry and Chemical Engineering, Fujian Normal University, Fuzhou, 350007, People’s Republic of China
    2. Fujian Key Laboratory of Polymer Materials, Fuzhou, 350007, People’s Republic of China
  • 刊物类别:Chemistry and Materials Science
  • 刊物主题:Chemistry
    Organic Chemistry
    Food Science
    Crystallography
  • 出版者:Springer Netherlands
  • ISSN:1573-1111
文摘
By using β-cyclodextrin aromatic aldehyde derivatives 5 and 6 as starting materials, the novel β-cyclodextrin-[60]fullerene conjugate 7 and bis-β-cyclodextrin-[60]fullerene conjugate 8 were designed and conveniently synthesized via the Huisgen [2+3] cycloaddition for the first time. The UV–Vis complexation experiments, fluorescence titration spectra and complexation ESI–MS spectrum suggested that they possessed excellent binding abilities for dyes with 1:1 host–guest complexes. The highest association constant of compound 8 for Orange I was as high as 6.97 × 105. Keywords β-Cyclodextrin [60]fullerene Synthesis Complexation Dye

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700