Proton-assisted iron(III) recognition with 4,4′-(4,5-diaminonaphthalen-1,8-yldiazo)-bisbenzenesulfonate

Yu Jiuan Cheng, Wei Ching Liao, Chong Mou Wang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)


Azo compounds, including 4,4′-(4,5-diaminonaphthalen-1,8-yldiazo)-bisbenzenesulfonate (DBS), 4,5-bis-(4-nitro-phenylazo)-naphthlene-1,8-diamine (NND), 4-(4-aminophen-1-ylazo)-benzenesulfonic acid (ABS), 4-(4-aminonaphthalen-1-ylazo)-benzenesulfonic acid (ANBS) and 1,1′-(4,5-diaminonaphthalen-1,8-diylazo)-bisbenzene (DNB) were synthesized and characterized for their potential in Fe3+ recognition in acidic solutions. DBS interacts specifically with Fe3+ in HCl solution, resulting in a significant alteration of the absorption and emission spectra. According to the spectral changes, DBS probably forms a 1:1 complex with Fe3+; the equilibrium constant was estimated to be ∼105 M-1. Replacing Fe3+ with Fe2+, Ni2+, Al3+ and Cr3+ or substituting NND, ABS, ANBS and DNB for DBS did not yield similar results, indicating that a configuration of two sulfonate groups is essential for Fe3+ chelation. DBS can be modified on glassy carbon and Au-sputtered quartz crystal electrodes (Au-QCM, fo = 9 MHz), via azotization and in situ electrochemical deazotization processes in HCl solution. When immobilized on QCM, DBS showed ability to attract Fe3+ from the solution phase, leading to a linear relationship between log{divides}Δf{divides} and log[Fe3+] over the range 10-4-10-3 M in 0.01 M HCl, with little interference from Fe2+ and Cr3+. Accordingly, DBS is a promising receptor for Fe3+ in acidic conditions.

Original languageEnglish
Pages (from-to)15-21
Number of pages7
JournalJournal of Electroanalytical Chemistry
Issue number1
Publication statusPublished - 2008 Jan 1


  • Azo dye
  • Electrochemical quartz crystal microbalance
  • Fe
  • Ion recognition

ASJC Scopus subject areas

  • Analytical Chemistry
  • General Chemical Engineering
  • Electrochemistry


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