Meso-Tetraarylporpholactones as high pH sensors

Gamal E. Khalil, Pedro Daddario, Kimberly S F Lau, Sayed Imtiaz, Michelle King, Martin Gouterman, Alexey Sidelev, Narissa Puran, Masoud Ghandehari, Christian Brückner

Research output: Contribution to journalArticlepeer-review


The ability of meso-tetra(pentafluorophenyl)porpholactone (TFPL) and its Pt(ii) complex [meso-tetra(pentafluorophenyl)porpholactonato]Pt(ii) (TFPLPt) to function as optical high pH sensors is described. Under strongly alkaline or high methoxide conditions, their UV-vis spectra undergo dramatic and reversible red-shifts. The dynamic range for the sensor T FPLPt in solution is from pH 11.5 to 13.2. Using 1H, 19F, and 13C NMR, UV-vis and IR spectroscopy, mass spectrometry, and the use of model compounds, the molecular origin of this optical shift is deduced to be a nucleophilic attack of OH-/MeO - on the lactone carbonyl of the chromophore, representing a novel mechanism for porphyrin-based sensors. The sensing compound was solubilized with Cremophor EL® for use in aqueous solutions and embedded in polymer matrixes for testing as optical fiber-based optodes and planar sheet optode materials.

Original languageEnglish (US)
Pages (from-to)2125-2131
Number of pages7
Issue number8
StatePublished - Aug 2010

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Environmental Chemistry
  • Spectroscopy
  • Electrochemistry


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