Synthesis of carbohydrate-conjugated azaphthalocyanine complexes for PDT

Park, Jong Min; Song, Cheol Jun; Wang, Yao; Jung, Chang Young; Hyun, In Ho; Seong, Dong Hoon; Jaung, Jae Yun

doi:10.1016/j.tetlet.2015.05.065

Cited by 8 publications

(9 citation statements)

References 21 publications

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“…Various NMR 1D and 2D techniques, accompanied by literature data allowed to assign hydrogens and carbons to signals appearing in the 1 H and 13 C NMR spectra. There were not many correlations present in the 1 H-1 H COSY and 1 H- 13 C HMBC NMR spectra. Therefore, signals resulting from the hydrogens belonging to cyclohexane ring (b-f, Figure 1) were assigned following the data obtained in the study and analyzed together with that previously obtained by other authors.…”

Section: Synthesis and Characterizationmentioning

confidence: 84%

“…UV-Vis spectra were measured on a Hitachi UV/VIS U-1900 spectrophotometer. 1 H NMR, 13 C NMR spectra were recorded using a Bruker Avance III spectrometer working at 500.25 MHz for 1 H and 125.79 MHz for 13 C at the Institute of Bioorganic Chemistry Polish Academy of Sciences in Poznan. Chemical shifts (δ) are quoted in parts per million (ppm) and referred to a residual solvent peak, whereas coupling constants (J) are quoted in Hertz (Hz).…”

Section: General Proceduresmentioning

confidence: 99%

“…Tetrapyrazinoporphyrazines constitute a distinct class of Pcs aza-analogues. Both metalfree tetrapyrazinoporphyrazines and their metal complexes have demonstrated interesting optical and electrochemical properties and also potential applications in technology and medicine [9][10][11][12][13][14][15][16]. Tetrapyrazinoporphyrazines similarly to Pcs reveal comparable abilities to generate singlet oxygen [17].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Physicochemical Properties of [(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]-thiophen-5-yl-substituted Tetrapyrazinoporphyrazine with Magnesium(II) Ion

Lijewski

Tydlitát

Czarczyńska-Goślińska

et al. 2021

Applied Sciences

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Tetrapyrazinoporphyrazine with peripheral menthol-thiophenyl substituents was synthesized using Linstead conditions and purified by flash column chromatography. The optimized synthetic and purification procedures allowed us to obtain a new macrocycle with 36% yield. Tetrapyrazinoporphyrazine derivative was characterized by UV–Vis and NMR spectroscopy, as well as MS spectrometry. Complex NMR studies using 1D and 2D NMR techniques allowed the analysis of the bulky menthol-thiophenyl substituted periphery of the new macrocycle. Further, photochemical stability and singlet oxygen quantum yield were determined by indirect method with diphenylisobenzofuran. The new tetrapyrazinoporphyrazine revealed low generation of singlet oxygen with a quantum yield of singlet oxygen formation at 2.3% in dimethylformamide. In turn, the macrocycle under irradiation with visible light presented very high stability with quantum yield for photostability of 9.59 × 10−6 in dimethylformamide, which figures significantly exceed the border for its classification as a stable porphyrinoid (10−4–10−5).

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Section: Synthesis and Characterizationmentioning

confidence: 84%

Section: General Proceduresmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Physicochemical Properties of [(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]-thiophen-5-yl-substituted Tetrapyrazinoporphyrazine with Magnesium(II) Ion

Lijewski

Tydlitát

Czarczyńska-Goślińska

et al. 2021

Applied Sciences

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“…Park and co-workers also reported the synthesis of the more hydrophilic A 3 B-type azaphthalocyanine zinc(II) complexes ZnPc14a and ZnPc14b. These Pcs contain three bulky three-dimensional bornane groups and one or two β-d-glucosyl or β-d-galactosyl moieties [29]. The authors have envisaged that the presence of the bornane groups could prevent the axial or peripheral approach between photosensitizers (PSs) without altering their optical properties.…”

Section: Phthalocyanine-carbohydrate Conjugatesmentioning

confidence: 99%

Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 2—Azides, Phthalocyanines, Subphthalocyanines and Porphyrazines

et al. 2020

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The reaction between organic azides and alkyne derivatives via the Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) is an efficient strategy to combine phthalocyanines and analogues with different materials. As examples of such materials, it can be considered the following ones: graphene oxide, carbon nanotubes, silica nanoparticles, gold nanoparticles, and quantum dots. This approach is also being relevant to conjugate phthalocyanines with carbohydrates and to obtain new sophisticated molecules; in such way, new systems with significant potential applications become available. This review highlights recent developments on the synthesis of phthalocyanine, subphthalocyanine, and porphyrazine derivatives where CuAAC reactions are the key synthetic step.

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“…In traditional applications, dyes have been used to colour textiles . Nowadays, dyes are being employed in many fields that require high technology, such as energy , biotechnology , and information technology . In the display industry, especially liquid crystal displays (LCDs), colour filters (CFs) are key components used as sensors in scanning devices to convert coloured graphics or text into digitised information through the colour filter layer from back light .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of yellow pyridonylazo colorants and their application in dye–pigment hybrid colour filters for liquid crystal display

Park

Jung

Wang

et al. 2016

Coloration Technology

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Nine yellow azo dyes were designed and synthesised by using different diazo components and pyridonyl coupling components for application in dye-pigment hybrid colour filters for liquid crystal displays. The synthesised dyes were characterised by proton nuclear magnetic resonance and elemental analysis. The thermal stability was examined by thermogravimetric analysis, and solubility was estimated in industrial solvents such as N-methyl-2-pyrrolidone and propylene glycol methyl ether acetate. The dyes, which exhibited suitable physical properties for use in a dye-pigment hybrid colour filter, were fabricated into colour filters, and their optical properties were measured. Coloration Technology Society of Dyers and Colourists 158

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Synthesis of carbohydrate-conjugated azaphthalocyanine complexes for PDT

Cited by 8 publications

References 21 publications

Synthesis and Physicochemical Properties of [(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]-thiophen-5-yl-substituted Tetrapyrazinoporphyrazine with Magnesium(II) Ion

Synthesis and Physicochemical Properties of [(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]-thiophen-5-yl-substituted Tetrapyrazinoporphyrazine with Magnesium(II) Ion

Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 2—Azides, Phthalocyanines, Subphthalocyanines and Porphyrazines

Synthesis of yellow pyridonylazo colorants and their application in dye–pigment hybrid colour filters for liquid crystal display

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