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Issue 8, 2010
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meso-Tetraarylporpholactones as high pH sensors

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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 TFPLPt 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.

Graphical abstract: meso-Tetraarylporpholactones as high pH sensors

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The article was received on 20 Jan 2010, accepted on 16 May 2010 and first published on 15 Jun 2010

Article type: Paper
DOI: 10.1039/C0AN00018C
Citation: Analyst, 2010,135, 2125-2131

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    meso-Tetraarylporpholactones as high pH sensors

    G. E. Khalil, P. Daddario, K. S. F. Lau, S. Imtiaz, M. King, M. Gouterman, A. Sidelev, N. Puran, M. Ghandehari and C. Brückner, Analyst, 2010, 135, 2125
    DOI: 10.1039/C0AN00018C

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