The synthesis and molecular recognition study of β-cyclodextrin derivatives modified by spiro[2H-benzopyran-2,2′-indoline]

Original Article


In this study, we adopted the condensation reaction between the aldehyde group in spiro[2H-benzopyran-2,2′-indoline] and the ethylene diamine in β-cyclodextrins to synthesize 1,3,3-trimethyl-6′-mono-(6-deoxy-ethylenediimine-β-cyclodextrin)-spiro[2H-benzopyran-2,2′-indoline] (β-CD-SPBI). The structure of the target compound was characterized by elemental analysis, NMR and IR spectroscopy. The UV–Vis and fluorescence spectroscopy were investigated in different solvents. The preliminary study of its molecular recognition was also conducted. The results indicated that β-CD-SPBI existed as two structural isomers, both of which showed significant fluorescent characteristics and β-CD-SPBI could showed the capacity of dual molecular recognition of a drug, ribavirin.


Spiro[2H-benzopyran-2,2′-indoline] Cyclodextrin derivative Spectral properties Molecular recognition 








This research is financially supported by Shaanxi Province Natural Science Foundation of China under the grant number of 2007B16.


  1. 1.
    Keita, H., Hiroshi, I., Asao, N., Akihiko, U., Fujio, T., Iwao, S., et al.: Fluorescent sensors of molecular recognition. Modified cyclodextrins capable of exhibiting guest-responsive twisted intramolecular charge transfer fluorescence. J. Am. Chem. Soc. 115, 5035–5040 (1993)CrossRefGoogle Scholar
  2. 2.
    Khan, A.R., Forgo, P., Stine, K.J., D’Souza, V.T.: Methods for selective modifications of cyclodextrins. Chem. Rev. 98, 1977–1996 (1998)CrossRefGoogle Scholar
  3. 3.
    Liu, Y., You, C.C., Zhang, H.Y.: Supramolecular chemistry—Molecular Recognition and Assembly of Synthetic Receptors, pp. 207–248. Nankai University Press, Tianjin (2001)Google Scholar
  4. 4.
    Wang, H., Mei, M.H., Xie, H.Z., Fang, Y., Zhang, X.H., Wu, S.K.: Photo-physical behavior of modified cyclodextrin by dimethylamino chalcone in different solvents. Acta Phys. Chim. Sin. 18, 495–499 (2002)Google Scholar
  5. 5.
    Chen, Y., Han, N., Yang, H., Liu, Y.: Synthesis of triazinylanilino-bridged bis(β-cyclodextrin)s and their selective binding behaviors with dyes. Acta Chim. Sin. 65, 1076–1080 (2007)Google Scholar
  6. 6.
    Tetsuo, K., Hiroki, N., Masato, N., Akihiko, U.: Color change indicators for molecules using methyl red-modified cyclodextrins. Anal. Chem. 71, 2844–2849 (1999)CrossRefGoogle Scholar
  7. 7.
    Shao, N., Jin, J.Y., Wang, H., Zhang, Y., Yang, R.H., Chan, W.H.: Tunable photochromism of spirobenzopyran via selective metal ion coordination: an efficient visual and rationing fluorescent probe for divalent copper ion. Anal. Chem. 80, 3466–3475 (2008)CrossRefGoogle Scholar
  8. 8.
    Kimura, K.: Photocontrol of ionic conduction by photochromic crown ethers. Coord. Chem. Rev. 148, 41–61 (1996)CrossRefGoogle Scholar
  9. 9.
    Shao, N., Zhang, Y., Cheung, S.M., Yang, R.H., Chan, W.H., Mo, T., et al.: Copper ion-selective fluorescent sensor based on the inner filter effect using a spiropyran derivative. Anal. Chem. 77, 7294–7303 (2005)CrossRefGoogle Scholar
  10. 10.
    Huang, Y.D., Yu, H.T., Wang, Y.M., Meng, J.B.: Synthesis and properties of β-cyclodextrin bearing a spiro[2H-benzopyran-2,2′-indoline] moiety. Chem. J. Chin. Univ. 22, 1685–1687 (2001)Google Scholar
  11. 11.
    Liu, X., Li, Z.J.: Thermal decoloration behavior of the colored species from aldehydoindolinospirobenzopyrans. Chemistry 4, 43–46 (1993)Google Scholar
  12. 12.
    Liu, Y.Y., Fan, X.D., Gao, L.: Synthesis and characterization of β-cyclodextrin based functional monomers and its copolymers with N-isopropylacrylamide. Macromol. Biosci. 3, 715–719 (2003)CrossRefGoogle Scholar
  13. 13.
    Tong, L.H.: Cyclodextrin Chemistry—Fundamentals and Applications, pp. 154. Science Press, Beijing (2001)Google Scholar

Copyright information

© Springer Science+Business Media B.V. 2010

Authors and Affiliations

  1. 1.School of Chemistry and Chemical EngineeringXianyang Normal UniversityXianyangChina

Personalised recommendations