Derivatization and in situ metallation of phthalocyanines using click chemistry

Yılmaz, Yusuf; Şener, M. Kasım; Erden, İbrahim; Avcıata, Ulvi

doi:10.1016/j.poly.2009.07.033

Cited by 26 publications

(5 citation statements)

References 32 publications

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“…This compound was obtained from the CuAAC reaction of the alkynyl-substituted phthalocyanine CuPc8 with 2-acetamido-2-deoxy-β-d-glucopyranosyl azide 2 (Scheme 9) [26]. Phthalocyanine CuPc8 was obtained by cyclotetramerization of dimethyl (3,4-dicyanophenyl)propargylmalonate, in pentan-1-ol and in the presence of DBU [27]. The 1,3-dipolar cycloaddition took place in THF, at room temperature, in the presence of CuSO 4 •5H 2 O and sodium ascorbate.…”

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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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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“…Alkynyl substituted MPc complexes are known , and the synthesis of Mn tetrakis(5‐hexyn‐oxy) phthalocyanine (complex 1 , Scheme ) employed in this work has been reported . However, apart from our recent report on alkynyl substituted FePc , there are no reports on electrode modification using click chemistry and alkynyl Pcs.…”

Section: Introductionmentioning

confidence: 99%

Electrode Modification Using Alkyne Manganese Phthalocyanine and Click Chemistry for Electrocatalysis

2016

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In this work, azidobenzene diazonium salt is grafted onto a glassy carbon electrode (GCE) followed by clicking of manganese tetrahexynyl phthalocyanine for the electrocatalysis of hydrazine. The GCE was first grafted via the in situ diazotization of a diazonium salt, rendering the GCE surface layered with azide groups. From this point, the 1,3‐dipolar cycloaddition reaction, catalyzed by a copper catalyst was utilized to ‘click’ the manganese tetrahexynyl phthalocyanine to the surface of the grafted GCE. This new platform was then characterized using cyclic voltammetry (CV), scanning electrochemical microscopy (SECM) and X‐ray photoelectron spectroscopy (XPS). Based on the cyclic voltammetry calibration curve of electrocatalysis for hydrazine, the clicked Mn phthalocyanine electrode proved to be an effective sensor with a sensitivity of 27.38 µA mM−1 and the limit of detection (LoD) of 15.4 pM which is a great improvement compared to other reported sensors for this analyte.

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“…23 The best known click reaction is the copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition between azides and alkynes and is less used for the synthesis of substituted phthalocyanines. [24][25][26][27][28] Recently we have shown the syntheses of new symmetrical and unsymmetrical Pcs with terminal alkynyl substituents starting from phthalonitrile bearing a terminal alkynyl moiety without the protection/deprotection concept and their click reaction with azide-end functional polymers. 29,30 To the best of our knowledge, there is only one example of nonperipherally terminal alkynyl substituted phthalocyanine, that is 1,8,15,22-tetrakis(propargyloxy)phthalocyaninato-zinc(II) announced by Leznoff and coworkers in 1998.…”

Section: Introductionmentioning

confidence: 99%

The synthesis and characterization of nonperipherally tetra terminal alkynyl substituted phthalocyanines and glycoconjugation via the click reaction

Kanat

Dinçer

2014

Dalton Trans.

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In order to obtain nonperipherally tetra terminal alkynyl substituted phthalocyanines (Pcs), new 3-pent-4-ynyloxy phthalonitrile (3) was prepared by the nucleophilic displacement reaction of 3-nitrophthalonitrile (1) and 4-pentyn-1-ol (2) and then cyclotetramerization was attained in the presence of zinc acetate, cobalt acetate, and/or DBU in n-pentanol without protection/deprotection. For the first time, the glycoconjugation of the nonperipherally tetra terminal alkynyl substituted zinc phthalocyanine (ZnPc) (6) can be easily achieved via the click reaction in a high yield. The electronic absorption spectrum of the glucopyranosyl substituted ZnPc (10) derivative showed a red-shifted Q band at 751 nm in dichloromethane due to the protonation of the meso nitrogens of the Pc macrocycle. Deacylation yielded ZnPc (11) bearing glucose substituents at nonperipheral positions with an improved water-solubility and non-aggregation in DMSO. The chemical structures of the new compounds were characterized by (1)H NMR, (13)C NMR, FT-IR, UV-Vis, mass spectrometry and elemental analysis. Moreover, the phthalonitrile compound was characterized using X-ray.

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Derivatization and in situ metallation of phthalocyanines using click chemistry

Cited by 26 publications

References 32 publications

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

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

Electrode Modification Using Alkyne Manganese Phthalocyanine and Click Chemistry for Electrocatalysis

The synthesis and characterization of nonperipherally tetra terminal alkynyl substituted phthalocyanines and glycoconjugation via the click reaction

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