Synthesis and properties of a novel alkylselenium substituted phthalocyanine

Riega, Sergio D. Ezquerra; Vior, María C. García; Awruch, Josefina

doi:10.1016/j.tetlet.2015.05.027

Cited by 5 publications

(4 citation statements)

References 23 publications

(22 reference statements)

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“…Interestingly, due to reducing the conjugate electrons of the phthalocyanine plane, the 2D‐G@PFePc shows a Q‐band maximum of 677.3 nm with a blueshift of the Q‐band maximum of pure PFePc (Figure 3c). [15, 26] While the Q‐band maximum of 3D‐G‐PFePc shows almost no change compared with the PFePc, indicating most of monolayer PFePc nanosheets are chemically longitudinal‐linked to graphene by the strong covalent bonding.…”

Section: Resultsmentioning

confidence: 98%

Longitudinally Grafting of Graphene with Iron Phthalocyanine‐based Porous Organic Polymer to Boost Oxygen Electroreduction

Huang

et al. 2023

Angew Chem Int Ed

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Iron phthalocyanine‐based polymers (PFePc) are attractive noble‐metal‐free candidates for catalyzing oxygen reduction reaction (ORR). However, the low site‐exposure degree and poor electrical conductivity of bulk PFePc restricted their practical applications. Herein, laminar PFePc nanosheets covalently and longitudinally linked to graphene (3D‐G‐PFePc) was prepared. Such structural engineering qualifies 3D‐G‐PFePc with high site utilization and rapid mass transfer. Thence, 3D‐G‐PFePc demonstrates efficient ORR performance with a high specific activity of 69.31 μA cm−2, a high mass activity of 81.88 A g−1, and a high turnover frequency of 0.93 e s−1 site−1 at 0.90 V vs. reversible hydrogen electrode in O2‐saturated 0.1 M KOH, outperforming the lamellar PFePc wrapped graphene counterpart. Systematic electrochemical analyses integrating variable‐frequency square wave voltammetry and in situ scanning electrochemical microscopy further underline the rapid kinetics of 3D‐G‐PFePc towards ORR.

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Section: Resultsmentioning

confidence: 98%

Longitudinally Grafting of Graphene with Iron Phthalocyanine‐based Porous Organic Polymer to Boost Oxygen Electroreduction

Huang

et al. 2023

Angew Chem Int Ed

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“…Singlet dioxygen quantum yields measured in DMSO at room temperature using 1,3‐diphenylisobenzofuran (DPBF) as the chemical 1 O 2 monitor are listed in Table 1. All compounds proved to be equally efficient photosensitizers if compared with other zinc(II) phthalocyanines [30,48] …”

Section: Resultsmentioning

confidence: 99%

“…All compounds proved to be equally efficient photosensitizers if compared with other zinc(II) phthalocyanines. [30,48] No remarkable photobleaching of the Pcs was observed during the 1 O 2 generation experiments, while exhibiting photostability during the irradiation time (see Figures S175-S184). Besides, the DPBF self-sensitized photoperoxidation rate was negligible compared to DPBF consumption due to photosensitized 1 O 2 .…”

Section: Singlet Dioxygen Photoproductionmentioning

confidence: 97%

A Case‐Study on the Photophysics of Chalcogen‐Substituted Zinc(II) Phthalocyanines

Ezquerra Riega,

Gutierrez Suburu,

Rodríguez

et al. 2024

Chemistry A European J

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Singlet dioxygen has been widely applied in different disciplines such as medicine (photodynamic therapy or blood sterilization), remediation (wastewater treatment) or industrial processes (fine chemicals synthesis). Particularly, it can be conveniently generated by energy transfer between a photosensitizer's triplet state and triplet dioxygen upon irradiation with visible light. Among the best photosensitizers, substituted zinc(II) phthalocyanines are prominent due to their excellent photophysical properties, which can be tuned by structural modifications, such as halogen‐ and chalcogen‐atom substitution. These patterns allow for the enhancement of spin‐orbit coupling, commonly attributed to the heavy atom effect, which correlates with the atomic number ( ) and the spin‐orbit coupling constant ( ) of the introduced heteroatom. Herein, a fully systematic analysis of the effect exerted by chalcogen atoms on the photophysical characteristics (absorption and fluorescence properties, lifetimes and singlet dioxygen photogeneration), involving 30 custom‐made β‐tetrasubstituted chalcogen‐bearing zinc(II) phthalocyanines is described and evaluated regarding the heavy atom effect. Besides, the intersystem crossing rate constants are estimated by several independent methods and a quantitative profile of the heavy atom is provided by using linear correlations between relative intersystem crossing rates and relative atomic numbers. Good linear trends for both intersystem crossing rates (S1‐T1 and T1‐S0) were obtained, with a dependency on the atomic number and the spin‐orbit coupling constant scaling as and , respectively The trend shows to be independent of the solvent and temperature.

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“…According to these observations, the bioisosteric replacement of the heteroatom attached to the phthalocyanine macrocycle should be studied since it can cause significant modifications in the photophysical and photodynamic properties that could be useful for the PDT requirements. We have reported the first synthesis of a lipophilic alkylselenium tetrasubstituted zinc(II) phthalocyanine which presented a Φ ∆ of 0.64, a fluorescence quantum yield (Φ F ) production of 0.18 and a high Q band absorption coefficient which is relevant for dosing in PDT studies [20].…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Novel hydro- and lipo-philic selenium zinc(II) phthalocyanines: Synthesis, photophysical properties and photodynamic effects on CT26 colon carcinoma cells

et al. 2018

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The synthesis and photochemical properties of two novel selenium zinc(II) phthalocyanines, a lipid-soluble 2,9(10),16(17),23(24)-tetrakis[(2-dimethylamino)ethylselanyl]phthalocyaninato zinc(II) (4) and its water-soluble quaternized derivative 2,9(10),16(17),23(24)-tetrakis[(2trimethylammonium)ethylselanyl]phthalocyaninato zinc(II) tetraiodide (5), were investigated. Maximum absorption values were 689 nm and 684 nm for 4 and 5 in DMF, respectively. In addition, phthalocyanines were revealed to be very efficient singlet oxygen generators with high values of Φ ∆ 0.74 and 0.84 for 4 and 5 in DMF, and they were photostable over the irradiation times studied. The photodynamic effect were evaluated on CT26 colon carcinoma cells. After light exposure, 4 and 5 were found to be cytotoxic, and IC 50 values were 0.5 ± 0.1 µM and 2.3 ± 0.6 µM, respectively. The production of a greater amount of reactive oxygen species after phthalocyanines irradiation would be responsible for its potent phototoxic action on CT26 colon carcinoma cells.

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Synthesis and properties of a novel alkylselenium substituted phthalocyanine

Cited by 5 publications

References 23 publications

Longitudinally Grafting of Graphene with Iron Phthalocyanine‐based Porous Organic Polymer to Boost Oxygen Electroreduction

Longitudinally Grafting of Graphene with Iron Phthalocyanine‐based Porous Organic Polymer to Boost Oxygen Electroreduction

A Case‐Study on the Photophysics of Chalcogen‐Substituted Zinc(II) Phthalocyanines

Novel hydro- and lipo-philic selenium zinc(II) phthalocyanines: Synthesis, photophysical properties and photodynamic effects on CT26 colon carcinoma cells

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