Preparation and optical properties of polyimide films linked with porphyrinato Pd (II) and Pt (II) complexes through a triazine ring and application toward oxygen sensors

Kimura, Takeshi; Watanabe, Shuichi; Sawada, Shin–ichi; Shibasaki, Yuji; Oishi, Yoshiyuki

doi:10.1002/pola.28469

Cited by 7 publications

(5 citation statements)

References 39 publications

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“…The presence of Pt-porphyrins allows for a reversible fluorescence response at different O 2 concentrations reducing the detection limit for dissolved O 2 in water to 4.7 μmol L −1 . Recently, the use of copolymers of fluorescent porphyrins has also been discussed by Kimura and collaborators (Kimura et al, 2017 ). 5-(3-Aminophenyl)-10,15,20-tristolylporphyrinato complexes of Pt (II) and Pd(II) were utilized as building blocks for the formation of polyimide polymers (PIPs) (Figure 7 ).…”

Section: Optical Sensing Approaches: the Role Of Oxygen Quenchingmentioning

confidence: 99%

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Oxygen Sensing, Hypoxia Tracing and in Vivo Imaging with Functional Metalloprobes for the Early Detection of Non-communicable Diseases

2018

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Hypoxia has been identified as one of the hallmarks of tumor environments and a prognosis factor in many cancers. The development of ideal chemical probes for imaging and sensing of hypoxia remains elusive. Crucial characteristics would include a measurable response to subtle variations of pO2 in living systems and an ability to accumulate only in the areas of interest (e.g., targeting hypoxia tissues) whilst exhibiting kinetic stabilities in vitro and in vivo. A sensitive probe would comprise platforms for applications in imaging and therapy for non-communicable diseases (NCDs) relying on sensitive detection of pO2. Just a handful of probes for the in vivo imaging of hypoxia [mainly using positron emission tomography (PET)] have reached the clinical research stage. Many chemical compounds, whilst presenting promising in vitro results as oxygen-sensing probes, are facing considerable disadvantages regarding their general application in vivo. The mechanisms of action of many hypoxia tracers have not been entirely rationalized, especially in the case of metallo-probes. An insight into the hypoxia selectivity mechanisms can allow an optimization of current imaging probes candidates and this will be explored hereby. The mechanistic understanding of the modes of action of coordination compounds under oxygen concentration gradients in living cells allows an expansion of the scope of compounds toward in vivo applications which, in turn, would help translate these into clinical applications. We summarize hereby some of the recent research efforts made toward the discovery of new oxygen sensing molecules having a metal-ligand core. We discuss their applications in vitro and/or in vivo, with an appreciation of a plethora of molecular imaging techniques (mainly reliant on nuclear medicine techniques) currently applied in the detection and tracing of hypoxia in the preclinical and clinical setups. The design of imaging/sensing probe for early-stage diagnosis would longer term avoid invasive procedures providing platforms for therapy monitoring in a variety of NCDs and, particularly, in cancers.

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Section: Optical Sensing Approaches: the Role Of Oxygen Quenchingmentioning

confidence: 99%

“… Different examples of metallaporphyrins supported in polymeric matrices (PtTPP/TPMA Mao, Y. et al, 2017 , PIPs (Kimura et al, 2017 ), CoP (Röösli et al, 1997 ), Pt/Pd-PTA (Önal et al, 2016 ) applied in the sensing of molecular oxygen. …”

Section: Optical Sensing Approaches: the Role Of Oxygen Quenchingmentioning

confidence: 99%

Oxygen Sensing, Hypoxia Tracing and in Vivo Imaging with Functional Metalloprobes for the Early Detection of Non-communicable Diseases

2018

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“…The following are available online at http://www.mdpi.com/2227-9040/8/2/29/s1, Figure S1: UV-vis spectra of Pt(II)-TAPP (the same concentration 3 × 10 −5 M) in different solvents: hexane (1); chlorobenzene (2); tetrahydrofuran (3); chloroform (4); dichloromethane (5); benzonitrile (6); dimethylformamide (7); dimethylsulfoxide (8). Effect of the solvent polarity on the intensity and position of the bands, Figure S2: Effect of the solvent polarity on the position and intensity of the bands in fluorescence spectra of Pt(II)-TAPP (the same concentration 3 × 10 −5 M), in: hexane (1); chlorobenzene (2); tetrahydrofuran (3); chloroform (4); dichloromethane (5); benzonitrile (6); dimethylformamide (7); dimethylsulfoxide (8).…”

Section: Supplementary Materialsmentioning

confidence: 99%

“…The detection is based on the reversible fluorescence response of the Pt-porphyrin to different concentrations of dissolved O 2 in water. Based on the same method, other platinum fluorescent compound, Pt(II)-5-(3-aminophenyl)-10,15,20-tris-(p-tolyl)-porphyrin, incorporated in polyimide polymers was capable of detecting oxygen in concentrations up to 10% [7].Composite strips comprising Pt(II)-meso-tetrakis-(pentafluorophenyl)-porphyrin and cadmium telluride quantum dots were used for rapid colorimetric determination [8,9] of oxygen. High fluorescence quantum yield hybrid materials based on phenylacetylide fibers functionalized with platinum (II) meso-tetraphenylporphyrins were developed and showed improved sensitivity to O 2 , providing a detection limit of 7.5 ppm.…”

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Novel Platinum-Porphyrin as Sensing Compound for Efficient Fluorescent and Electrochemical Detection of H2O2

et al. 2020

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Metalloporphyrins are highly recognized for their capacity to act as sensitive substances used in formulation of optical, fluorescent, and electrochemical sensors. A novel compound, namely Pt(II)-5,10,15,20-tetra-(4-allyloxy-phenyl) porphyrin, was synthesized by metalation with PtCl2(PhCN)2 of the corresponding porphyrin base and was fully characterized by UV-vis, fluorimetry, FT-IR, 1H-NMR, and 13C-NMR methods. The fluorescence response of this Pt-porphyrin in the presence of different concentrations of hydrogen peroxide was investigated. Besides, modified glassy carbon electrodes with this Pt-porphyrin (Pt-Porf-GCE) were realized and several electrochemical characterizations were comparatively performed with bare glassy carbon electrodes (GCE), in the absence or presence of hydrogen peroxide. The Pt-porphyrin demonstrated to be a successful sensitive material for the detection of hydrogen peroxide both by fluorimetric method in a concentration range relevant for biological samples (1.05–3.9 × 10−7 M) and by electrochemical method, in a larger concentration range from 1 × 10−6 M to 5 × 10−5 M. Based on different methods, this Pt-porphyrin can cover detection in diverse fields, from medical tests to food and agricultural monitoring, proving high accuracy (correlation coefficients over 99%) in both fluorimetric and electrochemical measurements.

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Preparation and Optical and Electrochemical Properties of Phthalocyanines with Four or Eight Diphenylphosphino, Diphenylphosphoryl, and Diphenylthiophosphinyl Groups

et al. 2018

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Several phthalocyanines (Pcs), in which four or eight phosphines are directly linked to their periphery, have been prepared. The starting materials, 4‐(diphenylphosphino)‐5‐chlorophthalonitrile (2), 4,5‐bis(diphenylphosphino)phthalonitrile (3), and 4‐(diphenylphosphino)‐5‐(diphenylphosphoryl)‐phthalonitrile (4), were prepared by the reaction of 4,5‐dichlorophthalonitrile (1) and diphenyltrimethylsilylphosphine in toluene at 110 °C. Compound 2 was treated with Li in hexan‐1‐ol at 120 °C, to produce β‐tetrakis(diphenylphosphino)tetrachloroPc [Pc(PPh2)4Cl4, 11], while refluxing 3 in ethoxyethanol in the presence of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) yielded β‐octakis(diphenylphosphino)Pc [Pc(PPh2)8, 12]. The reactions of 11 with mCPBA or elemental sulfur produced β‐tetrakis(diphenylphosphoryl)tetrachloroPc [Pc(POPh2)4Cl4, 13] or β‐tetrakis(diphenylthiophosphinyl)tetrachloroPc [Pc(PSPh2)4Cl4, 15], respectively, whereas that of 12 with mCPBA or elemental sulfur afforded β‐octakis(diphenylphosphoryl)Pc [Pc(POPh2)8, 14] or β‐octakis(diphenylthiophosphinyl)Pc [Pc(PSPh2)8, 16], respectively. β‐Octakis(diphenylphosphino)‐α‐octafluorophthalocyaninato magnesium [Pc(PPh2)8F8Mg, 17] was prepared from tetrafluorophthalonitrile (6) in two‐step reactions. The structures of simplified model compounds 11a–16a were optimized using DFT methods with the Gaussian 09 program. The optimized structures were utilized to calculate the HOMO and LUMO orbital energies, and the electronic transitions in the absorption spectra by the TD‐DFT method.

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Preparation and optical properties of polyimide films linked with porphyrinato Pd (II) and Pt (II) complexes through a triazine ring and application toward oxygen sensors

Cited by 7 publications

References 39 publications

Oxygen Sensing, Hypoxia Tracing and in Vivo Imaging with Functional Metalloprobes for the Early Detection of Non-communicable Diseases

Oxygen Sensing, Hypoxia Tracing and in Vivo Imaging with Functional Metalloprobes for the Early Detection of Non-communicable Diseases

Novel Platinum-Porphyrin as Sensing Compound for Efficient Fluorescent and Electrochemical Detection of H2O2

Preparation and Optical and Electrochemical Properties of Phthalocyanines with Four or Eight Diphenylphosphino, Diphenylphosphoryl, and Diphenylthiophosphinyl Groups

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