meso-Tetraarylporpholactones as high pH sensors

The ability of meso-tetra(pentafluorophenyl)porpholactone (T(F)PL) and its Pt(II) complex [meso-tetra(pentafluorophenyl)porpholactonato]Pt(II) (T(F)PLPt) to function as optical high pH sensors is described. Under strongly alkaline or high methoxide conditions, their UV-vis spectra undergo dramatic a...

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Bibliographic Details
Published in:Analyst (London) 2010-08, Vol.135 (8), p.2125-2131
Main Authors: KHALIL, Gamal E, DADDARIO, Pedro, LAU, Kimberly S. F, IMTIAZ, Sayed, KING, Michelle, GOUTERMAN, Martin, SIDELEV, Alexey, PURAN, Narissa, GHANDEHARI, Masoud, BRÜCKNER, Christian
Format: Article
Language:English
Subjects:
Analytical chemistry
Chemistry
Dynamic range
Electrochemistry
Electrodes
Exact sciences and technology
General, instrumentation
Hydrogen-Ion Concentration
Infrared radiation
Lactones
Mathematical models
Organoplatinum Compounds - chemical synthesis
Organoplatinum Compounds - chemistry
Porphyrins - chemical synthesis
Porphyrins - chemistry
Sensors
Spectra
Spectrometric and optical methods
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Summary:The ability of meso-tetra(pentafluorophenyl)porpholactone (T(F)PL) and its Pt(II) complex [meso-tetra(pentafluorophenyl)porpholactonato]Pt(II) (T(F)PLPt) 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(F)PLPt in solution is from pH 11.5 to 13.2. Using (1)H, (19)F, and (13)C 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.
ISSN:0003-2654
1364-5528
DOI:10.1039/c0an00018c