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 journalArticle

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 languageEnglish (US)
Pages (from-to)2125-2131
Number of pages7
JournalAnalyst
Volume135
Issue number8
DOIs
StatePublished - Aug 2010

Fingerprint

pH sensors
sensor
Optical Fibers
Molecular Models
Porphyrins
Sensors
Lactones
Chromophores
Ultraviolet spectroscopy
Polymer matrix
Mass spectrometry
Optical fibers
Infrared spectroscopy
Mass Spectrometry
Spectrum Analysis
porphyrin
Polymers
Nuclear magnetic resonance
nuclear magnetic resonance
Testing

ASJC Scopus subject areas

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

Cite this

Khalil, G. E., Daddario, P., Lau, K. S. F., Imtiaz, S., King, M., Gouterman, M., ... Brückner, C. (2010). Meso-Tetraarylporpholactones as high pH sensors. Analyst, 135(8), 2125-2131. https://doi.org/10.1039/c0an00018c

Meso-Tetraarylporpholactones as high pH sensors. / Khalil, Gamal E.; Daddario, Pedro; Lau, Kimberly S F; Imtiaz, Sayed; King, Michelle; Gouterman, Martin; Sidelev, Alexey; Puran, Narissa; Ghandehari, Masoud; Brückner, Christian.

In: Analyst, Vol. 135, No. 8, 08.2010, p. 2125-2131.

Research output: Contribution to journalArticle

Khalil, GE, Daddario, P, Lau, KSF, Imtiaz, S, King, M, Gouterman, M, Sidelev, A, Puran, N, Ghandehari, M & Brückner, C 2010, 'Meso-Tetraarylporpholactones as high pH sensors', Analyst, vol. 135, no. 8, pp. 2125-2131. https://doi.org/10.1039/c0an00018c
Khalil GE, Daddario P, Lau KSF, Imtiaz S, King M, Gouterman M et al. Meso-Tetraarylporpholactones as high pH sensors. Analyst. 2010 Aug;135(8):2125-2131. https://doi.org/10.1039/c0an00018c
Khalil, Gamal E. ; Daddario, Pedro ; Lau, Kimberly S F ; Imtiaz, Sayed ; King, Michelle ; Gouterman, Martin ; Sidelev, Alexey ; Puran, Narissa ; Ghandehari, Masoud ; Brückner, Christian. / Meso-Tetraarylporpholactones as high pH sensors. In: Analyst. 2010 ; Vol. 135, No. 8. pp. 2125-2131.
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