High pH sensing with water-soluble porpholactone derivatives and their incorporation into a Nafion® optode membrane

The Analyst ◽  
2015 ◽  
Vol 140 (1) ◽  
pp. 190-196 ◽  
Author(s):  
Jill L. Worlinsky ◽  
Steven Halepas ◽  
Masoud Ghandehari ◽  
Gamal Khalil ◽  
Christian Brückner
Keyword(s):  
Metal Complexes ◽  
Water Soluble ◽  
Ph Sensing ◽  
Free Base ◽  
Aryl Group ◽  
High Ph ◽  
Optode Membrane

The known optical high pH sensing chromophores, free base and metal complexes (M = 2H, Zn(ii), Pt(ii)) of meso-tetrakis(pentafluorophenyl)porpholactone, and the as yet untested Ga(iii) complex, were made freely water-soluble by derivatization at the aryl group with PEG chains.

scholarly journals Oxazolochlorins 21. Most Efficient Access to meso-Tetraphenyl- and meso-Tetrakis(pentafluorophenyl)porpholactones, and Their Zinc(II) and Platinum(II) Complexes

Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4351
Author(s):  
Damaris Thuita ◽  
Dinusha Damunupola ◽  
Christian Brückner
Keyword(s):  
Metal Complexes ◽  
Biomedical Applications ◽  
Free Base ◽  
Aryl Group ◽  
Efficient Access ◽  
Metal Derivatives

meso-Phenyl- and meso-pentafluorophenyl-porpholactones, their metal complexes, as well as porphyrinoids directly derived from them are useful in a number of technical and biomedical applications, and more uses are expected to be discovered. About a dozen competing and complementary pathways toward their synthesis were reported. The suitability of the methods changes with the meso-aryl group and whether the free base or metal derivatives are sought. These circumstances make it hard for anyone outside of the field of synthetic porphyrin chemistry to ascertain which pathway is the best to produce which specific derivative. We report here on what we experimentally evaluated to be the most efficient pathways to generate the six key compounds from the commercially available porphyrins, meso-tetraphenylporphyrin (TPP) and meso-tetrakis(pentafluorophenyl)porphyrin (TFPP): free base meso-tetraphenylporpholactone (TPL) and meso-tetrakis(pentafluorophenyl)porpholactone (TFPL), and their platinum(II) and zinc(II) complexes TPLPt, TFPLPt, TPLZn, and TFPLZn, respectively. Detailed procedures are provided to make these intriguing molecules more readily available for their further study.

Oxazolochlorins 11: Tuning the dynamic high pH sensing range of [meso-tetraarylporpholactonato]M(II) complexes by variation of the central metal ion, the aryl substituents, and introduction of a β-nitro group

2013 ◽  
Vol 17 (08n09) ◽  
pp. 836-849 ◽  
Author(s):  
Jill L. Worlinsky ◽  
Gloria Zarate ◽  
Matthias Zeller ◽  
Masoud Ghandehari ◽  
Gamal Khalil ◽  
...  
Keyword(s):  
Metal Ion ◽  
Central Metal ◽  
The Novel ◽  
Ph Sensing ◽  
Ph Sensors ◽  
X Ray Diffraction ◽  
Aryl Group ◽  
X Ray ◽  
High Ph ◽  
Sensing Range

Based on the high pH-sensing ability of [meso-tetrakis(pentafluorophenyl) porpholactonato]-platinum(II), we investigated the influence of the metal ( M = Zn ( II ), Ni ( II ), Cu ( II ), Pd ( II ), Ag ( II ), Pt ( II )), the aryl group ( Ar = C 6 H 5, C 6 F 5), and the presence of a β- NO 2 group on the pH sensing range. The syntheses of the novel β-nitroporpholactone derivatives are described, and their regiochemistry deduced by spectroscopic and single crystal X-ray diffraction methods. The UV-vis base titration midpoints for all derivatives were determined in an aqueous solution containing a surfactant, showing that the metal has the least influence, thus identifying a cheaper and easier method to prepare porpholactone M complex-based high pH-sensors. The influence of the pentafluorophenyl groups and the β-nitration were comparable with respect to their ability to increase the nucleophilicity of the porpholactone toward hydroxide, but the optical response for the pentafluorophenyl-substituted derivative were stronger. β-Nitration and pentafluorophenyl-substitution had additive effects.

Synthesis and characterization of water-soluble free-base, zinc and copper porphyrin–oligonucleotide conjugates

2008 ◽  
Vol 16 (13) ◽  
pp. 6544-6551 ◽  
Author(s):  
Angela Mammana ◽  
Tomohiro Asakawa ◽  
Klaus Bitsch-Jensen ◽  
Amanda Wolfe ◽  
Saireudee Chaturantabut ◽  
...  
Keyword(s):  
Water Soluble ◽  
Synthesis And Characterization ◽  
Free Base ◽  
Copper Porphyrin ◽  
Oligonucleotide Conjugates

scholarly journals Cyclopentadienone Iron Tricarbonyl Complexes-Catalyzed Hydrogen Transfer in Water

Molecules ◽  
2020 ◽  
Vol 25 (2) ◽  
pp. 421 ◽  
Author(s):  
Daouda Ndiaye ◽  
Sébastien Coufourier ◽  
Mbaye Diagne Mbaye ◽  
Sylvain Gaillard ◽  
Jean-Luc Renaud
Keyword(s):  
Metal Complexes ◽  
Hydrogen Transfer ◽  
Low Cost ◽  
Pure Water ◽  
Free Water ◽  
Water Soluble ◽  
Tricarbonyl Complex ◽  
Reaction Conditions ◽  
Catalytic Systems ◽  
Iron Tricarbonyl

The development of efficient and low-cost catalytic systems is important for the replacement of robust noble metal complexes. The synthesis and application of a stable, phosphine-free, water-soluble cyclopentadienone iron tricarbonyl complex in the reduction of polarized double bonds in pure water is reported. In the presence of cationic bifunctional iron complexes, a variety of alcohols and amines were prepared in good yields under mild reaction conditions.

scholarly journals Ratiometric pH Sensing and Imaging in Living Cells with Dual-Emission Semiconductor Polymer Dots

Molecules ◽  
2019 ◽  
Vol 24 (16) ◽  
pp. 2923
Author(s):  
Piaopiao Chen ◽  
Iqra Ilyas ◽  
Su He ◽  
Yichen Xing ◽  
Zhigang Jin ◽  
...  
Keyword(s):  
Fluorescent Dyes ◽  
Resonance Energy Transfer ◽  
Resonance Energy ◽  
Fluorescein Isothiocyanate ◽  
Water Soluble ◽  
Ph Sensing ◽  
Dual Emission ◽  
Polymer Dots ◽  
Ratiometric Ph Sensing

Polymer dots (Pdots) represent newly developed semiconductor polymer nanoparticles and exhibit excellent characteristics as fluorescent probes. To improve the sensitivity and biocompatibility of Pdots ratiometric pH biosensors, we synthesized 3 types of water-soluble Pdots: Pdots-PF, Pdots-PP, and Pdots-PPF by different combinations of fluorescent dyes poly(9,9-dioctylfluorenyl-2,7-diyl) (PFO), poly[(9,9-dioctyl-fluorenyl-2,7-diyl)-co-(1,4-benzo-{2,1′,3}-thiadazole)] (PFBT), and fluorescein isothiocyanate (FITC). We found that Pdots-PPF exhibits optimal performance on pH sensing. PFO and FITC in Pdots-PPF produce pH-insensitive (λ = 439 nm) and pH-sensitive (λ = 517 nm) fluorescence respectively upon a single excitation at 380 nm wavelength, which enables Pdots-PPF ratiometric pH sensing ability. Förster resonance energy transfer (FRET) together with the use of PFBT amplify the FITC signal, which enables Pdots-PPF robust sensitivity to pH. The emission intensity ratio (I517/I439) of Pdots-PPF changes linearly as a function of pH within the range of pH 3.0 to 8.0. Pdots-PPF also possesses desirable reversibility and stability in pH measurement. More importantly, Pdots-PPF was successfully used for cell imaging in Hela cells, exhibiting effective cellular uptake and low cytotoxicity. Our study suggests the promising potential of Pdots-PPF as an in vivo biomarker.

Ion transfer and adsorption of water-soluble metal complexes of 8-hydroxyquinoline derivatives at the water|1,2-dichloroethane interface

2020 ◽  
Vol 856 ◽  
pp. 113566
Author(s):  
Sho Yamamoto ◽  
Shohei Kanai ◽  
Marie Takeyama ◽  
Yoshio Nishiyama ◽  
Hisanori Imura ◽  
...  
Keyword(s):  
Metal Complexes ◽  
Water Soluble ◽  
Ion Transfer ◽  
Adsorption Of Water

Colorimetric assay for the rapid determination of free-base nicotine in e-liquid

2020 ◽  
Vol 12 (2) ◽  
pp. 193-199
Author(s):  
Yan-Jun Huang ◽  
Qi-Xin Deng ◽  
Hong-Qiao Lan ◽  
Zheng-Zhong Fang ◽  
Hui Chen ◽  
...  
Keyword(s):  
Rapid Determination ◽  
Colorimetric Assay ◽  
Water Soluble ◽  
Free Base ◽  
Base Form

Nicotine exists in e-liquids primarily as the monoprotonated form and free-base form. The free-base form could be evaluated by use of a water-soluble indicator.

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