Phenyl-calix[4]arene-based fluorescent sensors: Cooperative binding for carboxylates

Xiao Hua Sun, Wenye Li, Ping Fang Xia, Hai Bin Luo, Yingli Wei, Ricky M S WONG*, Yuen Kit CHENG, Shaomin Shuang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

56 Citations (Scopus)

Abstract

Tetrakis-(4-carbamoylphenyl)-substituted and tetrakis-(4-amidophenyl)- substituted calix[4]arenes as well as the monomeric biphenylcarbamate have been synthesized as fluorescent receptors for anion sensing. Their binding properties with various anions including F-, CH3COO-, Ph-COO-, and H2PO4- were investigated by fluorescence titrations, Job plot experiments, 1H NMR spectroscopies, and ESI-MS measurements. Importantly, we have found that calix[4]arene-based sensors exhibit greatly enhanced binding affinity and selectivity toward carboxylates. The binding associations of tetrakis-(4-carbamoylphenyl)-substituted calix[4]arene for carboxylates are 1-2 orders of magnitude greater than those of the monomeric biphenylcarbamate sensor. Such an enhancement in the binding affinity and selectivity is attributed to the cooperative binding of the multiple ligating groups as revealed from the ab inito DFT calculations. Although tetrakis-(4-amidophenyl)- substituted calix[4]arene exhibited relatively weaker binding affinity toward anions, its superior binding selectivity for acetate ion over fluoride ion is evident. Our results also suggest that carbamate functionality is a useful Ç-bond donor for hydrogen-bonding interactions in molecular recognition and supramolecular chemistry.

Original languageEnglish
Pages (from-to)2419-2426
Number of pages8
JournalJournal of Organic Chemistry
Volume72
Issue number7
DOIs
Publication statusPublished - 30 Mar 2007

Scopus Subject Areas

  • Organic Chemistry

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