The Synthesis of Some Phthalocyanines and Napthalocyanines Derived from Sterically Hindered Phenols

Brewis, Matthew; Clarkson, Guy J.; Humberstone, Paul; Makhseed, Saad; McKeown, Neil B.

doi:10.1002/(sici)1521-3765(19980904)4:9<1633::aid-chem1633>3.0.co;2-o

Cited by 66 publications

(31 citation statements)

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“…Third‐generation phthalonitrile 2c and all the di‐ t ‐butyl‐substituted phthalonitriles 2d‐2f did not undergo successful cyclizations under these conditions. However, lithium metal in refluxing pentanol proved effective in producing third‐generation phthalocyanine 3c as well as the t ‐butyl dendritic phthalonitriles 3d‐3f () 42 …”

Section: Resultsmentioning

confidence: 99%

Solution and Thin‐Film Aggregation Studies of Octasubstituted Dendritic Phthalocyanines

Kernag¹,

McGrath²

2009

Israel Journal of Chemistry

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The synthesis and solution and thin‐film characterization of eight octasubstituted dendritic phthalocyanines (Pcs) and their zinc complexes are reported. The Pc chromophore was substituted in the 2,3,9,10,16,17,23,24‐positions with three generations of benzylaryl ether dendrons with either a benzyl (3a‐3c) or 3,5‐di‐t‐butylbenzyl periphery (3d‐3f). Visible spectra in solution (CH2Cl2‐EtOH mixtures, toluene, THF, dioxane, acetone, and EtOAc) indicated a varying degree of chromophore aggregation that depended on solvent, dendrimer generation, and whether the Pc was metallated. Variable‐concentration visible spectroscopic studies were analyzed using a nonlinear least‐squares fitting procedure giving Kd values. These values further quantitated the observations that the t‐butyl‐substituted den‐drimers 3d‐3f were all less prone to aggregation in solution than the unsubstituted dendrimers 3a‐3c, with a monotonic decrease in Kd across the series 3a → 3b → 3c → 3d → 3e → 3f. Second‐generation t‐butyl‐substituted dendrimer 3f showed little to no aggregation in all solvents studied. Thin‐film studies indicated that the largest members of the two dendrimer groups, third‐generation 3c and second‐generation 3f, were largely monomeric as evidenced by split Q‐bands, similar to that seen in dilute CH2Cl2 solution when deposited via spin‐coating onto glass slides. The metallated zinc Pcs 4a‐4f all exhibited significantly less tendency toward aggregation in both solution and thin‐films than their unmetallated analogues.

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Section: Resultsmentioning

confidence: 99%

Solution and Thin‐Film Aggregation Studies of Octasubstituted Dendritic Phthalocyanines

Kernag¹,

McGrath²

2009

Israel Journal of Chemistry

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“…This implies that 3,3',3'',3'''-(NH2)4PcCu(II) is more thermally stable than4,4',4'',4'''-(NH2)4PcCu(II). This may be attributed to the fact that 3-substituted precursor can dictate predominant forms of the least structurally crowded and least soluble phthalocyanine [22]. The other reason may be due to steric hindrance raised from the formation of the hydrogen bonding between hydrogen atom of the amino groups of 3Pc and the nitrogen of Aza Bridge to form hexagonal rings [23].…”

Section: Ftir Characterization Of Phthalocyaninatocopper(ii) Grafted mentioning

confidence: 99%

Sizing and Thermal Stability of Prepared Tetraaminophthalocyaninatocopper(II) Derivatives-grafted Polymers

Journal¹

2016

Baghdad Sci.J

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Different polymers were prepared by condensation polymerization of sebacic anhydride and adipic anhydride with ethylene glycol and poly(ethylene glycol). Their number average molecular weights were determined by end group analysis. Then, they were grafted on the prepared phthalocyaninatocopper(II) compounds with the general formula (NH2)4PcCu(II) having amino groups of 3,3',3'',3'''- or 4,4',4'',4'''- positions. All prepared polymers, compounds, and phthalocyaninatocopper(II)-grafted polymers were characterized by FTIR. The sizing measurements were carried out in 3,3',3'',3'''- (NH2)4PcCu(II) and 4,4',4'',4'''- (NH2)4PcCu(II) compounds with and without grafting polymers. The results showed that the grafting process led to decreasing in particle size and increasing in surface area. The grafting process was reflected positively on the thermal degradation of 3,3',3'',3'''- (NH2)4PcCu(II) and 4,4',4'',4'''- (NH2)4PcCu(II) grafted polymers. They had higher thermal stability accompanied with higher char residue and T50% weight loss with 3,3',3'',3'''-(NH2)4PcCu(II) and their grafted polymers being the best.

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“…[1][2][3][4][5] However, controlling the Pc bulk material on a molecular level is a crucial requirement to improve the desired photophysical and opto(electronic) properties which can maximize their potential utility in the intended applications. [11][12][13][14][15][16][17] Many strategies have been attempted by several groups over the last decades to overcome the detrimental influence of aggregation by yielding new Pc materials with unique photophysical and optoelectronic properties tailored to the required applications. [11][12][13][14][15][16][17] Many strategies have been attempted by several groups over the last decades to overcome the detrimental influence of aggregation by yielding new Pc materials with unique photophysical and optoelectronic properties tailored to the required applications.…”

Section: Introductionmentioning

confidence: 99%

Photophysical and theoretical studies of peripherally halogenated octaphenoxyphthalocyanines

et al. 2015

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DFT and TD-DFT computational studies validated the experimental results and revealing details about the electronic structures of novel halogenated phthalocyanines. Fluorescence and singlet oxygen quantum yields analysis revealed two-dimensional heavy atom effect that influenced the photophysical parameters. 249x169mm (150 x 150 DPI)Peripherally substituted phthalocyanines with halogenated phenoxy groups containing different central metals (In(III), Ga(III), Mg(II) and Zn(II)) were synthesized. The X-ray analyses confirmed that the halogen atoms (Cl, Br) at the ortho positions were bulky enough to orient the phenoxy substituents perpendicularly relative to the Pc core and perfectly discouraged cofacial aggregation. The ground state geometry, HOMO/LUMO energies and the electronic properties were theoretically calculated for some complexes and corresponded well with experimental data. Analysis of fluorescence and singlet oxygen quantum yields revealed strong heavy atom effect provided by the central metal. Irrespective of the present halogen, indium(III) complexes were characterized by high singlet oxygen production and very low fluorescence while reverse data were obtained for Mg(II) complexes.

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The Synthesis of Some Phthalocyanines and Napthalocyanines Derived from Sterically Hindered Phenols

Cited by 66 publications

References 0 publications

Solution and Thin‐Film Aggregation Studies of Octasubstituted Dendritic Phthalocyanines

Solution and Thin‐Film Aggregation Studies of Octasubstituted Dendritic Phthalocyanines

Sizing and Thermal Stability of Prepared Tetraaminophthalocyaninatocopper(II) Derivatives-grafted Polymers

Photophysical and theoretical studies of peripherally halogenated octaphenoxyphthalocyanines

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