Novel redox receptors for ion-pair and α-amino acid: synthesis and complexation properties of calix[4]arene derivatives bearing large conjugated ferrocene groups

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Abstract

By reacting calix[4]arene 1,3-bi-hydrazide derivative (2) with formacylferrocene in “1 + 2” condensation mode, novel calix[4]arene derivative bearing two conjugated ferrocene groups (3) was obtained in yield of 88%. By reacting 1,3-bi-substituted [2-(p-formylphenyloxy)ethyloxy]-p-tert-butylcalix[4]arene (5) with 1,1′-diacetylferrocene hydrazone (4) in “1 + 1” condensation mode, novel calix[4]arene derivative with 1,3-substituted large conjugated ferrocene bridge (6) was synthesized in yield of 83%. The structures and conformations of new compounds were confirmed by elemental analyses, IR spectra, ESI-MS, 1H NMR, etc. The electrochemical cyclic voltammetry experiments revealed that compounds 3 and 6 possessed excellent reversible electrochemical properties. The 1H NMR titration study showed that compound 6 possessed excellent complexation abilities for NaH2PO4 and glycine in 1:1 host–guest complex with the association constants of 3,850 and 2,460 M−1, respectively.

Keywords

Calix[4]arene Ferrocene Complexation Redox Ion pair Amino acid 
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Notes

Acknowledgment

Financial supports from the National Natural Science Foundation of China (No. 20402002), Fujian Natural Science Foundation of China (No. 2009J01019) and Program for Excellent young researchers in University of Fujian Province (No. JA10056) were greatly acknowledged. Thanks to Dr. Shangjie for the help of complexation properties.

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Copyright information

© Springer Science+Business Media B.V. 2011

Authors and Affiliations

  • Fafu Yang
    • 1
    • 2
  • Zhiqiang Liu
    • 1
  • Biqiong Hong
    • 1
  • Hongyu Guo
    • 1
  1. 1.College of Chemistry and MaterialsFujian Normal UniversityFuzhouPeople’s Republic of China
  2. 2.Fujian Key Laboratory of Polymer MaterialsFuzhouPeople’s Republic of China

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