meso-Tetraarylporpholactones as high pH sensorsElectronic supplementary information (ESI) available: Details of the alternative preparations of TFPL and TFPLPt, 13C, 1H, and 19F NMR spectra, IR spectra, etc. of these and comparison compounds in the absence and presence of base, UV-vis spectra of TFPL in different solvents and the presence of different bases, UV-vis TFPL acid titrations, etc. See DOI: 10.1039/c0an00018cPart 3 of the series Oxazolochlorins. Part 2: J. Akhigbe, C. Ryppa, M. Zeller
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...
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Main Authors | , , , , , , , , , |
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Format | Journal Article |
Language | English |
Published |
19.07.2010
|
Online Access | Get full text |
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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.
meso
-Tetra(pentafluorophenyl)porpholactone and its Pt(
ii
) complex respond to strongly alkaline conditions (pH 11.5 to 13.2) with a dramatic shift of their UV-vis spectra. |
---|---|
Bibliography: | 13 C H, and of these and comparison compounds in the absence and presence of base, UV-vis spectra of PLPt F F NMR spectra, IR spectra 19 , See DOI Electronic supplementary information (ESI) available: Details of the alternative preparations of 2009 1 in different solvents and the presence of different bases, UV-vis T 10.1039/c0an00018c etc. acid titrations and Part 3 of the series Oxazolochlorins. Part 2: J. Akhigbe, C. Ryppa, M. Zeller and C. Brückner 4927-4933. PL 74 J. Org. Chem. |
ISSN: | 0003-2654 1364-5528 |
DOI: | 10.1039/c0an00018c |