The synthesis and dyes complexation properties of novel cyclodextrin derivatives with large conjugate acylhydrazone group

  • Zusheng Wang
  • Hongyu Guo
  • Fafu Yang
  • Yingmei Zhang
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Abstract

By reacting β-cyclodextrin with 4-(prop-2-ynyloxy)benzaldehyde, the cyclodextrins (CDs) aromatic aldehyde derivative 6 was prepared in yield of 80 % via click chemistry of the Huisgen [2 + 3] cycloaddition reaction. Further Schiff-base condensation of compound 6 with salicylic hydrazide, nicotinohydrazide, or 2,4-dinitrophenylhydrazine, novel cyclodextrin derivatives with large conjugate acylhydrazone group 7a, 7b and 7c were conveniently obtained in yields of 75–85 %. Their structures were confirmed by elemental analysis, FT-IR, ESI–MS and NMR spectra. Their complexation properties for Orange I and Neutral red were studied by fluorescence titration spectroscopy and complexation MS spectrum. The results suggested that these novel CDs derivatives with large conjugate acylhydrazone group showed excellent complexation abilities for the tested dyes. The association constants were higher than 104 and the highest associations constant was 5.85 × 104 for host 7a with OI. The 1:1 complexes were formed in DMSO solution.

Keywords

Cyclodextrin Acylhydrazone Synthesis Complexation Dye 
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Notes

Acknowledgments

Financial support from the National Natural Science Foundation of China (No: 21406036), Fujian Natural Science Foundation of China (No. 2014J01034), Fujian province science and technology key project (2014N0025) and the Program for Innovative Research Team in Science and Technology in Fujian Province University were greatly acknowledged.

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Copyright information

© Springer Science+Business Media Dordrecht 2015

Authors and Affiliations

  • Zusheng Wang
    • 1
  • Hongyu Guo
    • 1
  • Fafu Yang
    • 1
    • 2
  • Yingmei Zhang
    • 1
  1. 1.College of Chemistry and Chemical EngineeringFujian Normal UniversityFuzhouPeople’s Republic of China
  2. 2.Fujian Key Laboratory of Polymer MaterialsFuzhouPeople’s Republic of China

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