Metal-free phthalocyanine aggregation and binding with amines: Specific and general solvent effects on absorption and fluorescence properties

Wang, Tao; Zhang, Xianfu; Lu, Xulin

doi:10.1016/j.molstruc.2014.11.073

Cited by 19 publications

(5 citation statements)

References 40 publications

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“…This different behavior shows that the geometry of the substituent can influence the aggregation process of the phthalocyanines, which is generally attributed to the self-facial arrangement of a range of macrocycles [17]. In pure DMSO, the results also suggest differences in the aggregation process.…”

Section: Resultsmentioning

confidence: 98%

Photochemical and Photophysical Properties of Phthalocyanines Modified with Optically Active Alcohols

et al. 2015

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Three phthalocyanine derivatives were synthesized and characterized: one modified with a racemic mixture of 1-(4-bromophenyl)ethanol and two other macrocycles modified with each one of the enantioenriched isomers (R)-1-(4-bromophenyl)ethanol and (S)-1-(4-bromophenyl)ethanol. The compounds were characterized by 1 H-NMR spectroscopy, mass spectrometry, UV-Vis absorption, and excitation and emission spectra. Additionally, partition coefficient values and the quantum yield of the generation of oxygen reactive species were determined. Interestingly, the phthalocyanine containing a (R)-1-(4-bromophenyl)ethoxy moiety showed higher quantum yield of reactive oxygen species generation than other compounds under the same conditions. In addition, the obtained fluorescence microscopy and cell viability results have shown that these phthalocyanines have different interactions with mammary MCF-7 cells. Therefore, our results indicate that the photochemical and biological properties of phthalocyanines with chiral ligands should be evaluated separately for each enantiomeric species.

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Section: Resultsmentioning

confidence: 98%

Photochemical and Photophysical Properties of Phthalocyanines Modified with Optically Active Alcohols

et al. 2015

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“…However, 8-fold α-(3-pyridyloxy) Pc 3e and 6e exhibits high hydrophilicity and can be dissolved in methanol without N -quaternization. The Q-band of 3e in methanol showed a blue-shifted and broad peak and was attributed to the severe aggregation of Pcs in polar protic solvents . The observed weak fluorescence also indicated intermolecular energy transfer due to aggregation.…”

mentioning

confidence: 95%

“…The Q-band of 3e in methanol showed a blue-shifted and broad peak and was attributed to the severe aggregation of Pcs in polar protic solvents. 20 The observed weak fluorescence also indicated intermolecular energy transfer due to aggregation. Disaggregation of the Pc was achieved by addition of a Brønsted acid (Figure 4).…”

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confidence: 97%

Chemoselective Synthesis of Aryloxy-Substituted Phthalocyanines

Furuyama

Maeda

et al. 2019

J. Org. Chem.

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The synthesis of the first examples of 8-fold α-aryloxy-substituted phthalocyanines is described. 3,6-Diiodophthalonitrile was used as a precursor for a series of 3,6-aryloxy-substituted phthalonitriles, and a lead-mediated macrocyclization was employed to afford the corresponding free-base phthalocyanine complexes. The optical, electrochemical, and aggregation properties of these complexes can be tuned by varying the substituents on the aryloxy groups or by changing the pH value.

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“…The non-aggregation of these compounds can be provided by different ways such as; (i) the binding positions of the substitution form, (ii) the use of surfactants, (ii) and introduction of dendrimers on the phthalocyanine macrocycle. [20][21][22]…”

Section: Introduction *mentioning

confidence: 99%

Synthesis, characterization, aggregation and electrochemical properties of peripheral octa-2-{[4-(2-benzylphenoxy]benzyl]thio} ethoxy group substituted cobalt(II) phthalocyanine

Sağlam¹,

Bıyıklıoğlu²

2020

Rev.Roum.Chim.

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We were reported here, the synthesis, characterization, aggregation and electrochemical properties of 4,5-bis(2-{[4-(2- benzyl)phenoxy)benzyl]thio}ethoxy)phthalonitrile and 2,3,9,16, 17,23,24-octa[(2-{[4-(2-benzyl)phenoxy)benzyl]thio}ethoxy)] phthalociyaninatocobalt(II). CoPc were prepared by the reaction of 4,5-bis(2-{[4-(2-benzyl)phenoxy)benzyl]thio}ethoxy) phthalonitrile with the corresponding anhydrous metal salt in n-pentanol and DBU. The structures of the original compounds were identified by using elemental analysis, 1 H-NMR, 13C-NMR, IR, mass and UVvis spectroscopic data. Electrochemical redox characteristics of the compounds were determined by electroanalytical techniques such as cyclic voltammetry, square wave voltammetry. The aggregation tendencies and electrochemical redox properties of all phthalocyanines were investigated on the basis of central metal, solvent medium and substituent effects, using UV-Vis spectral.

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Metal-free phthalocyanine aggregation and binding with amines: Specific and general solvent effects on absorption and fluorescence properties

Cited by 19 publications

References 40 publications

Photochemical and Photophysical Properties of Phthalocyanines Modified with Optically Active Alcohols

Photochemical and Photophysical Properties of Phthalocyanines Modified with Optically Active Alcohols

Chemoselective Synthesis of Aryloxy-Substituted Phthalocyanines

Synthesis, characterization, aggregation and electrochemical properties of peripheral octa-2-{[4-(2-benzylphenoxy]benzyl]thio} ethoxy group substituted cobalt(II) phthalocyanine

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