A dihydrogen phosphate selective anion receptor based on acylhydrazone and pyrazole

Thiravidamani Senthil Pandian, Yusun Choi, Venkatesan Srinivasadesikan, Ming-Chang Lin*, Jongmin Kang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

A novel chromogenic anion receptor 1 based on acylhydrazone and pyrazole has been designed and synthesized. Chromogenic anion receptor 1 forms stable 1:1 complexes with dihydrogen phosphate (H2PO4-) and other halide (Cl-, Br-) anions in DMSO solution, as shown by UV-vis, fluorescence and 1H NMR spectroscopic experiments. The pyrazole containing host 1 in the optimized geometry of the complex has been noted as planar. The planarity of the host with the H2PO4- anion resulted from four strong N-H⋯O and two weak C-H⋯O types of H-bonding. In total six H-bonding and the planarity of the host in the complex are responsible for the high binding energy. The addition of an excess of more basic anions (F- and CH3COO-) induces stepwise deprotonation, an event signalled by the appearance of a bright yellow color. The intensity of the fluorescence spectrum increases when hydrogen bonding occurs and decreases when deprotonation occurs, which is evidenced by fluorescence titrations.

Original languageEnglish
Pages (from-to)650-658
Number of pages9
JournalNew Journal of Chemistry
Volume39
Issue number1
DOIs
StatePublished - 1 Jan 2015

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