Immobilization of Zinc Porphyrin Complexes on Pyridine-Functionalized Glass Surfaces

Dreas-Wlodarczak, Agnieszka; Müllneritsch, Michael; Juffmann, Thomas; Cioffi, Carla; Arndt, Markus; Mayor, Marcel

doi:10.1021/la100638u

Cited by 12 publications

(6 citation statements)

References 26 publications

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“…Indeed, previous reports suggest that ZnTPP presents strong affinity to pyridine, thiol and trithiocarbonate. 108 To clarify this finding, we have performed UV−visible spectroscopy of ZnTPP, ZnTPP/BTPA (SI, Figure S1) and ZnTPP/CPADB (SI, Figure S1) before and after light irradiation. In the presence of BTPA and ZnTPP, we observed a new signal at 620 nm, while the signals of ZnTPP/CPADB did not change.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The discrepancy in the polymerization rates can be attributed to the coordination of zinc to the thiocarbonylthio moiety on RAFT which may lead to higher efficiency of PET-RAFT activation. Indeed, previous reports suggest that ZnTPP presents strong affinity to pyridine, thiol and trithiocarbonate . To clarify this finding, we have performed UV–visible spectroscopy of ZnTPP, ZnTPP/BTPA (SI, Figure S1) and ZnTPP/CPADB (SI, Figure S1) before and after light irradiation.…”

Section: Results and Discussionmentioning

confidence: 99%

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Exploiting Metalloporphyrins for Selective Living Radical Polymerization Tunable over Visible Wavelengths

2015

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The use of metalloporphyrins has been gaining popularity particularly in the area of medicine concerning sensitizers for the treatment of cancer and dermatological diseases through photodynamic therapy (PDT), and advanced materials for engineering molecular antenna for harvesting solar energy. In line with the myriad functions of metalloporphyrins, we investigated their capability for photoinduced living polymerization under visible light irradiation over a broad range of wavelengths. We discovered that zinc porphyrins (i.e., zinc tetraphenylporphine (ZnTPP)) were able to selectively activate photoinduced electron transfer-reversible addition-fragmentation chain transfer (PET-RAFT) polymerization of trithiocarbonate compounds for the polymerization of styrene, (meth)acrylates and (meth)acrylamides under a broad range of wavelengths (from 435 to 655 nm). Interestingly, other thiocarbonylthio compounds (dithiobenzoate, dithiocarbamate and xanthate) were not effectively activated in the presence of ZnTPP. This selectivity was likely attributed to a specific interaction between ZnTPP and trithiocarbonates, suggesting novel recognition at the molecular level. This interaction between the photoredox catalyst and trithiocarbonate group confers specific properties to this polymerization, such as oxygen tolerance, enabling living radical polymerization in the presence of air and also ability to manipulate the polymerization rates (kp(app) from 1.2-2.6 × 10(-2) min(-1)) by varying the visible wavelengths.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

Exploiting Metalloporphyrins for Selective Living Radical Polymerization Tunable over Visible Wavelengths

2015

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“…However, it has been reported that zinc has a strong coordination for thiocarbonylthio moiety on RAFT agent and can promote the occurrence of PET‐RAFT polymerization. [ 20 ] This proves that the high‐efficiency synergy of perovskite and PCN‐222 can enhance the photocatalytic polymerization performance of the photocatalyst far beyond the role of TCPP and TCPP‐metallazed catalysts.…”

Section: Resultsmentioning

confidence: 90%

Binary Hybridization Strategy toward Stable Porphyrinic Zr‐MOF Encapsulated Perovskites as High‐Performance Heterogeneous Photocatalysts for Red to NIR Light‐Induced PET‐RAFT Polymerization

Xia

Shi

Zhu

et al. 2022

Adv Funct Materials

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Stable binary nanohybrids based on all-inorganic halide perovskite encapsulated in porphyrinic Zr-MOF (PCN-222) are constructed for photoinduced electron transfer-reversible addition-fragmentation chain transfer (PET-RAFT) polymerization. The synergistic effect of perovskite and PCN-222 endows the photocatalyst with high-efficiency photogenic charge carrier separation and light absorption property. CsPbI 3 @PCN-222 (20%) is finally screened out as the oxygen and solvent-resistant photocatalyst for highly efficient photocontrolled polymerization of conjugated and unconjugated monomers under red to near infrared (NIR) light with high monomer conversion and narrow molecular weight distribution well-defined polymers (Đ < 1.20). Controllable polymers and ultrahigh molecular weight polymers (up to 1730000 g mol −1 ) are successfully obtained by chain extension and block copolymerization of various monomers. The constructed photocatalysts easily achieve excellent light and temporal control, and even show high MMA conversion with NIR light under a thick barrier.

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“…However, in this polymerization system, the results were reversed due to the addition of Zn(TCPP), indicating that there is a special recognition mechanism between CDTPA and Zn(TCPP). Previous studies reported that Zn(TCPP) has a strong affinity for pyridines, thiols, and trithiocarbonates, thus leading to zinc coordination to the thiocarbonylthio groups on the RAFT chain transfer agent, which may be the reason for the obvious activation efficiency of CDTPA in Zn(TCPP)-mediated PET-RAFT. To test this guess, UV–vis spectroscopic analysis of Zn(TCPP) (curve c, Figure S1), Zn(TCPP)/CDTPA (curve a, Figure S1) and Zn(TCPP)/CPAD (curve b, Figure S1) were performed under illumination.…”

Section: Resultsmentioning

confidence: 99%

Ultrasensitive miRNA-21 Biosensor Based on Zn(TCPP) PET-RAFT Polymerization Signal Amplification and Multiple Logic Gate Molecular Recognition

Sun

Liu

Kong

et al. 2023

ACS Appl. Mater. Interfaces

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Quantitative measurement of microRNAs (miRNAs) is extremely important in plenty of biomedical applications especially cancer diagnosis but remains a great challenge. In this work, we developed a logic gate recognition biosensing platform based on the “trinity” molecular recognition mode for quantifying miRNAs with a detection limit of 4.48 aM, along with a linear range from 0.1 nM to 10 aM under optimal experimental conditions. In order to obtain excellent detection performance, we adopted a Zn(TCPP) photocatalytic electron transfer reversible addition-fragmentation chain transfer (PET-RAFT) polymerization signal amplification strategy. The light-induced PET-RAFT has developed green applications of free radical polymerization in the field of biosensors. This is the first report on the preparation of signal amplification biosensors using PET-RAFT for tumor marker detection. With the outstanding detection performance, we can apply the sensor system to the early screening of lung cancer patients.

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Immobilization of Zinc Porphyrin Complexes on Pyridine-Functionalized Glass Surfaces

Cited by 12 publications

References 26 publications

Exploiting Metalloporphyrins for Selective Living Radical Polymerization Tunable over Visible Wavelengths

Exploiting Metalloporphyrins for Selective Living Radical Polymerization Tunable over Visible Wavelengths

Binary Hybridization Strategy toward Stable Porphyrinic Zr‐MOF Encapsulated Perovskites as High‐Performance Heterogeneous Photocatalysts for Red to NIR Light‐Induced PET‐RAFT Polymerization

Ultrasensitive miRNA-21 Biosensor Based on Zn(TCPP) PET-RAFT Polymerization Signal Amplification and Multiple Logic Gate Molecular Recognition

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