Aggregation behavior in unsymmetrically substituted metal-free phthalocyanines

Kobak, Rabia Zeynep Uslu; Ari, Meral; Tekin, Adem; Gül, Ahmet

doi:10.1016/j.chemphys.2014.12.015

Cited by 7 publications

(2 citation statements)

References 31 publications

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“…Pcs and MPcs very often show a definite tendency to aggregate in solution, in particular in water or aqueous solvents, even when ionic substituents are present on the benzene rings. The aggregation state could be reliably estimated by means of spectroscopic techniques [9,14,15]. Aggregation could arise by simple stacking, driven by strong hydrophobic and π-interactions between the Pc rings, or also it depends on covalent interactions involving the central metal ions, linked each other by axial µ-oxo bridges.…”

Section: General Introductionmentioning

confidence: 99%

Metallophthalocyanines as Catalysts in Aerobic Oxidation

et al. 2021

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The first remarkable property associated to metallophthalocyanines (MPcs) was their chemical “inertness”, which made and make them very attractive as stable and durable industrial dyes. Nevertheless, their rich redox chemistry was also explored in the last decades, making available a solid and detailed knowledge background for further studies on the suitability of MPcs as redox catalysts. An overlook of MPcs and their catalytic activity with dioxygen as oxidants will be discussed here with a special emphasis on the last decade. The mini-review begins with a short introduction to phthalocyanines, from their structure to their main features, going then through the redox chemistry of metallophthalocyanines and their catalytic activity in aerobic oxidation reactions. The most significant systems described in the literature comprise the oxidation of organosulfur compounds such as thiols and thiophenes, the functionalization of alkyl arenes, alcohols, olefins, among other substrates.

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Section: General Introductionmentioning

confidence: 99%

Metallophthalocyanines as Catalysts in Aerobic Oxidation

et al. 2021

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“…Dyes and catalysts (1)(2)(3)(4), organic photovoltaic devices (5)(6)(7)(8)(9)(10), photodynamic therapy (11)(12)(13)(14), and electrochemical applications (15)(16)(17)(18) are phthalocyanines' widespread applications stemmed from peripheral functionalization of them. New properties of phthalocyanines arise from their conjugated macrocyclic units.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Chalcone Substituted Metallophthalocyanines: Electrochemistry, Spectroelectrochemistry and Catalytic Oxidation of 2-mercaptoethanol

Karaca¹

2018

Journal of the Turkish Chemical Society Section A: Chemistry

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Novel metallophthalocyanines (M = Zn, Co) carrying four (E)-1-(furan-2-yl)-3-(4hydroxyphenyl)prop-2-en-1-one (chalcone) at the peripheral positions were sythesized. These complexes have been characterized by a combination of infrared spectroscopy (FT-IR), proton NMR (1 H-NMR), high resolution mass spectroscopy (HRMS), and ultraviolet visible (UV-Vis) spectrophotometry techniques. Also, cyclic voltammograms of these phthalocyanines were recorded and zinc phthalocyanine has one and cobalt phthalocyanine has two reduction reactions. Spectroelectrochemical investigation shows the ring-based reduction of MPcs. Pc-7 cobalt(II) phthalocyanine was investigated as a catalyst in the catalytic oxidation of 2mercaptoethanol. Turnover number, initial reaction rate, and the oxygen consumption were found in the catalytic oxidation of 2-mercaptoethanol as 16.6, 0.29, 2.52, respectively.

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Helical Self‐Assembly of Optically Active Glycoconjugated Phthalocyanine J‐Aggregates

2019

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Four galactoconjugated zinc(II) phthalocyanines (Pcs) have been prepared and fully characterized. The carbohydrate‐containing phthalonitrile precursors of the Pcs were synthesized through a copper‐catalysed azide‐alkyne cycloaddition (CuAAC). The Pcs show a remarkable aggregation behaviour in solution, depending on the nature of the solvent, the temperature and the substitution position on the phthalocyanine. Solvent‐dependent CD‐spectroscopy experiments show that these Pcs aggregate as chiral helices in solution. Crystal structure data of a phthalocyanine bearing two carbohydrate units substantiate the properties shown by CD spectroscopy. Furthermore, the 1,2,3‐triazole moieties of the Pcs play a decisive role in the formation of supramolecular aggregates. The glycoconjugated zinc(II) phthalocyanines described here show molar extinction coefficients ϵmax>105 M−1 cm−1 and absorption maxima λmax>680 nm, which make them attractive photosensitizers for Photodynamic Therapy (PDT).

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Aggregation behavior in unsymmetrically substituted metal-free phthalocyanines

Cited by 7 publications

References 31 publications

Metallophthalocyanines as Catalysts in Aerobic Oxidation

Metallophthalocyanines as Catalysts in Aerobic Oxidation

Synthesis of Novel Chalcone Substituted Metallophthalocyanines: Electrochemistry, Spectroelectrochemistry and Catalytic Oxidation of 2-mercaptoethanol

Helical Self‐Assembly of Optically Active Glycoconjugated Phthalocyanine J‐Aggregates

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