Isolation, spectroscopic properties, and electrochemical properties of two oligomeric silicon phthalocyanines

DeWulf, David W.; Leland, Jonathan K.; Wheeler, B. L.; Bard, Allen J.; Batzel, D.A.; Dininny, D. R.; Kenney, Malcolm E.

doi:10.1021/ic00249a012

Cited by 72 publications

(36 citation statements)

References 5 publications

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“…[13] The cyclic voltammogram of 3 b is similar in shape to that of the m-oxo dimer 5 b, except for the regions of aggregation peaks, and this strongly suggests that compound 3 b is indeed a dimer (the number of redox couples of cofacial oligomers increases with increasing number of constituent units). [13] The voltammogram of 6 differs completely from those of the above three compounds in that the first reduction potential is much more negative, so that it is even more negative than the second reduction potentials of 3 b, 4 b, and 5 b. The first oxidation and reduction couples are reversible if the sweeps are returned after recording these couples between À 1.5 and 1.0 V, while irreversibility increases if the potentials are widened to À 2 to 1.5 V. In any case, there is no similarity between the voltammograms of the SiÀSi Pc dimer 3 b and SiTBC 6, and this precludes the possibility that 3 b contains the TBC structure.…”

Section: Identification Of the Dimeric Structurementioning

confidence: 76%

“…[12] As shown by Kenney et al for m-oxo dimeric SiPcs, the redox couples of the m-oxo dimer 5 b result from splitting of the redox couples in monomeric SiPcs, that is, in this case monomer 4 b. [13] The cyclic voltammogram of 3 b is similar in shape to that of the m-oxo dimer 5 b, except for the regions of aggregation peaks, and this strongly suggests that compound 3 b is indeed a dimer (the number of redox couples of cofacial oligomers increases with increasing number of constituent units). [13] The voltammogram of 6 differs completely from those of the above three compounds in that the first reduction potential is much more negative, so that it is even more negative than the second reduction potentials of 3 b, 4 b, and 5 b.…”

Section: Identification Of the Dimeric Structurementioning

confidence: 99%

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Synthesis and Characterization of Phthalocyanines with Direct Si−Si Linkages

et al. 2002

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Several cofacial phthalocyanines (Pcs) with an Si−Si linkage were obtained by one‐step condensation of 1H‐isoindole‐1,3(2H)‐diimine with hexachlorodisilane as template in quinoline. They were characterized by gel‐permeation chromatography, IR, NMR spectroscopy, and mass spectrometry, and cyclic voltammetry. The results strongly suggest that we indeed obtained Pc dimers directly linked by an Si−Si bond using this novel concept of utilizing a compound/salt with an element–element bond as a template. The cofacial dimer structures are reasonably supported by X‐ray absorption near‐edge structure (XANES), electronic absorption and magnetic circular dichroism (MCD) spectra, and molecular orbital (MO) calculations. Interestingly, they show an electronic absorption spectrum very similar to that of silicon tetrabenztriazacorrole (SiTBC).

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Section: Identification Of the Dimeric Structurementioning

confidence: 76%

Section: Identification Of the Dimeric Structurementioning

confidence: 99%

Synthesis and Characterization of Phthalocyanines with Direct Si−Si Linkages

et al. 2002

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“…Monosilylated SiPc, SiPc(OH)(OSi(CH 3 ) 2 C 8 H 17 ) (L 1 =OH, L 2 =OSi(CH 3 ) 2 C 8 H 17 ), was prepared by reaction of SiPc(OH) 2 and chlorodimethyloctylsilane in pyridine at 60 °C 54. Dendrimer units were linked to the axial positions of SiPc by reaction with SiPc(OH) 2 or SiPc(OH)(OSi(CH 3 ) 2 C 8 H 17 ) in refluxing toluene 4.…”

Section: Methodsmentioning

confidence: 99%

Aromaticity of Giant Polycyclic Aromatic Hydrocarbons with Hollow Sites: Super Ring Currents in Super‐Rings

Hajgató

Deleuze

Ohno

2006

Chemistry A European J

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We present a systematic theoretical study based on semi-empirical, Hartree-Fock (HF), and density functional theory (DFT) models of a series of polycyclic aromatic hydrocarbons (PAHs) that exhibit hollow sites. In this study we focus particularly on the magnetic criteria of aromaticity, namely (1)H NMR and nucleus-independent chemical shifts (NICS), and on their relationships with other electronic properties. The computed shifts and NICS indices indicate that an external magnetic field induces exceptionally strong ring currents in even-layered PAH doughnuts, in particular in the layer directly adjacent to the central hole of double-layered compounds. These exceptionally strong ring currents also correlate with particularly small HOMO-LUMO gaps and electronic excitation energies and to abnormally high polarizabilities, indicating in turn that these compounds have a more pronounced metallic character. Comparison is made with further depictions of aromaticity in these systems and in [18]-[66]annulene rings by employing topological, structural, and energetic criteria.

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“…[53] Coupling of the diethyl 5-(bromomethyl)isophthalate end group with the 3,5-dihydroxybenzyl alcohol monomer was performed in refluxing acetone in the presence of K 2 CO 3 , was prepared by reaction of SiPc(OH) 2 and chlorodimethyloctylsilane in pyridine at 60 8C. [54] Dendrimer units were linked to the axial positions of SiPc by reaction with SiPc(OH) 2 or SiPc(OH)(OSi(CH 3 ) 2 C 8 H 17 ) in refluxing toluene. [4] Typical experimental conditions are given for (G3)SiPc below.…”

Section: Methodsmentioning

confidence: 99%

A Phthalocyanine Dendrimer Capable of Forming Spherical Micelles

Uchiyama

Ishii

Nonomura

et al. 2003

Chemistry A European J

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A novel and intrinsically spherical micelle has been prepared by utilizing a silicon phthalocyanine ((WG3)SiPc) that has a thin hydrophobic alkyl chain and a bulky hydrophilic poly(aryl ether) dendrimer with terminal carboxyl groups, as its two axial ligands. Gel-permeation chromatography and cryo-transmission electron microscopic experiments indicate that (WG3)SiPcs self-assemble to form a spherical micelle at very low concentrations in aqueous solution. Depending on the pH of the aqueous phase, (WG3)SiPc shuttles between aqueous and organic phases. In the presence of hydrophobic molecules, this transfer is accompanied by the inclusion of these (guest) molecules, indicating that the micelle acts as a molecular capsule with a nanospace surrounded by functional phthalocyanine planes.

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Isolation, spectroscopic properties, and electrochemical properties of two oligomeric silicon phthalocyanines

Cited by 72 publications

References 5 publications

Synthesis and Characterization of Phthalocyanines with Direct Si−Si Linkages

Synthesis and Characterization of Phthalocyanines with Direct Si−Si Linkages

Aromaticity of Giant Polycyclic Aromatic Hydrocarbons with Hollow Sites: Super Ring Currents in Super‐Rings

A Phthalocyanine Dendrimer Capable of Forming Spherical Micelles

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