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

doi:10.1039/c0an00018c

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 journal › Article › peer-review

Abstract

The ability of meso-tetra(pentafluorophenyl)porpholactone (T^FPL) and its Pt(ii) complex [meso-tetra(pentafluorophenyl)porpholactonato]Pt(ii) (T^FPLPt) 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 language	English (US)
Pages (from-to)	2125-2131
Number of pages	7
Journal	Analyst
Volume	135
Issue number	8
DOIs	https://doi.org/10.1039/c0an00018c
State	Published - Aug 2010

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Environmental Chemistry
Spectroscopy
Electrochemistry

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title = "Meso-Tetraarylporpholactones as high pH sensors",

abstract = "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{\textregistered} for use in aqueous solutions and embedded in polymer matrixes for testing as optical fiber-based optodes and planar sheet optode materials.",

author = "Khalil, {Gamal E.} and Pedro Daddario and Lau, {Kimberly S F} and Sayed Imtiaz and Michelle King and Martin Gouterman and Alexey Sidelev and Narissa Puran and Masoud Ghandehari and Christian Br{\"u}ckner",

year = "2010",

month = aug,

doi = "10.1039/c0an00018c",

language = "English (US)",

volume = "135",

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AU - Khalil, Gamal E.

AU - Daddario, Pedro

AU - Lau, Kimberly S F

AU - Imtiaz, Sayed

AU - King, Michelle

AU - Gouterman, Martin

AU - Sidelev, Alexey

AU - Puran, Narissa

AU - Ghandehari, Masoud

AU - Brückner, Christian

PY - 2010/8

Y1 - 2010/8

N2 - 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.

AB - 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.

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Meso-Tetraarylporpholactones as high pH sensors

Abstract

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