Diphenoxysilicon phthalocyanine

Joyner, Ralph D.; Cekada, J.; Linck, R. G.; Kenney, Malcolm E.

doi:10.1016/0022-1902(60)80072-3

Cited by 21 publications

(17 citation statements)

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“…In the early 1960's the groundwork for the synthesis of volatile cyclic tetrapyrrolic compounds was laid by Kenney and coworkers at Case Institute of Technology (Joyner, et al, 1960;Joyner and Kenney, 1962;Krueger and Kenney, 1963). Those workers synthesized a variety of silicon phthalocyanines (PcSi) with groups oxygen-bridged to the silicon (figure 3.l.a).…”

Section: Phthalocyaninesmentioning

confidence: 99%

Nitrogen isotopes in chlorophyll and the origin of Eastern Mediterranean sapropels

Sachs¹

1997

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The goals of this thesis were: (1) to establish methods for the determination of nitrogen and carbon isotope ratios in marine particulate and sedimentary chlorophyll derivatives; (2) to establish chlorophyll ()15N and ol3C as proxies for the nitrogen and carbon isotopic composition of marine phytoplankton; and (3) to use chlorophyll nitrogen isotopic ratios to understand the origin of Late Quaternary Eastern Mediterranean sapropels.Techniques are presented for the determination of chlorin nitrogen and carbon isotopic ratios in marine particles and sediments with a precision greater than 0.15 per mil for both isotopes. The procedure can be performed in about 4 hours for particulate and 8 hours for sediment samples, and relies on multiple chromatographic purifications. About 20 g of a moderately organic-rich sediment are required.A technique is also presented for the determination of chlorin nitrogen and carbon isotopic ratios by isotope-ratio monitoring gas chromatography-mass spectrometry (irmGC-MS) by synthesizing bis-(tert.-butyldimethylsiloxy)Si(IV) chlorin derivatives. However, yields for the 4-step synthesis were only about 5-6% and there was a net isotopic depletion of 1.2 (± 0.3) per mil in the derivative, relative to the starting material.These techniques are then used to show that the nitrogen isotopic difference between chlorophyll and whole cells in six species of marine phytoplankton is 5.16 ± 2.40 per mil. For carbon, the isotopic difference between chlorophyll and whole cells in five species of marine phytoplankton is -0.02 ± 2.12 per mil. A model of the distribution of 15N in phytoplankton is constructed and it is demonstrated that the interspecies variability observed for the nitrogen isotopic difference between chlorophyll and whole cells can be attributed to differences in iii the partitioning of cellular nitrogen between non-protein biochemicals. In the field, where mixed assemblages of phytoplankton prevail, the isotopic difference beween chlorophyll and whole cells is expected to tend toward the average value of 5.16 per mil.Finally, the average nitrogen isotopic composition of chlorins from six Late Quaternary Eastern Mediterranean sapropels ( -5.01 + 0.38 per mil) was found to be very similar to the o15N of chlorophyll from the modem deep chlorophyll maximum ( -6.38 ± 1.80 per mil) in the Eastern Mediterranean. In addition, sapropel photoautotrophic material, calculated from the chlorin o15N, had the same isotopic composition (0.15 per mil) as both bulk sapropel sediments (-0.08 ± 0.53 per mil) and deep water nitrate (-0.05 per mil). These data suggest (a) that bottom waters were anoxic, (b) that organic matter burial efficiency was enhanced, and (c) that oligotrophic conditions similar to today persisted, in the Eastern Mediterranean during sapropel deposition. These results contradict earlier interpretations of Late Quaternary bulk sedimentary o15N in the Eastern Mediterranean. The latter concluded that the pattern of high o15N values in intercalated marl oozes and low values in ...

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Section: Phthalocyaninesmentioning

confidence: 99%

Nitrogen isotopes in chlorophyll and the origin of Eastern Mediterranean sapropels

Sachs¹

1997

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“…Pcs containing Si(IV) are an attractive subclass of Pcs because of the elemental abundance and very low toxicity levels of silicon coupled with their low band gap (~1.7 eV). The SiPcs with axial oxygen-terminated ligands (alkoxide, siloxide, aryloxide, and carboxylate) have been known since the 1960s 28 , 29 and they have been applied as photosensitizing agents in photodynamic therapy 30 . Recently, SiPcs with siloxide and aryloxide ligands have found use as chromophores and fluorophores in DSSCs and OLEDs 31 , the latter with external quantum efficiencies of up to 4.5% 13 .…”

Section: Introductionmentioning

confidence: 99%

Near-Infrared Fluorescence of Silicon Phthalocyanine Carboxylate Esters

Pal

Varghese

Cordes

et al. 2017

Sci Rep

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Seven silicon(IV) phthalocyanine carboxylate esters (SiPcs, 1–7) with non-, partially- and per-fluorinated aliphatic (linear or branched at the alpha-carbon) and aromatic ester groups have been synthesized, their solid-state structures determined and their optoelectronic properties characterized. The SiPcs exhibit quasi-reversible oxidation waves (vs. Fc+/Fc) at 0.58–0.75 V and reduction waves at −0.97 to −1.16 V centered on the phthalocyanine ring with a narrow redox gap range of 1.70–1.75 V. Strong absorbance in the near-infrared (NIR) region is observed for 1–7 with the lowest-energy absorption maximum (Q band) varying little as a function of ester between 682 and 691 nm. SiPcs 1–7 fluorescence in the near-infrared with emission maxima at 691–700 nm. The photoluminescence quantum yields range from 40 to 52%. As a function of esterification, the SiPcs 1–7 exhibit moderate-to-good solubility in chlorinated solvents, such as 1,2-dichlorobenzene and chloroform.

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“…Dichloro(phthalocyaninato)silicon (1) was prepared and characterized in 1960 [12,17]. It was found that the two axial substituents on the central metal atom could be varied over a wide range and several derivatives were thus prepared [18].…”

Section: Synthesismentioning

confidence: 99%

“…Although the thermal stability of Si(Pc)(OH) 2 is worse than that of [Si(Pc)O] n , Si(Pc)(OH) 2 is considered to be a prospective material for photoelectric devices which are sensitive in the near-IR wavelength region [11]. Shortly after the first silicon phthalocyanine had been synthesized [12], several oligomeric and polymeric silicon phthalocyanines with silicon-oxygen backbones [7b, 13] were reported. Subsequently, the polymer was found to be a good conductor when doped with oxidants such as iodine [14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of dihydroxy silicon phthalocyanine tetrasulfonic acid and poly-μ-oxo silicon phthalocyanine tetrasulfonic acid

Gürek

Appel

Mikalo

et al. 2001

J. Porphyrins Phthalocyanines

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ABSTRACT:We describe the synthesis of tetrasulfonated silicon phthalocyanine and its oligomer product prepared by metal salt catalyzed polycondensation. The catalytic effect of H 2 O-free CaCl 2 in quinoline is used for the polycondensation of dihydroxy silicon phthalocyanine to the cofacially arrayed oligomer. Spectroscopic characterization and photoelectron spectroscopy data of the prepared compounds are reported. We present the first results on polypyrrole films doped with these substances.

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Diphenoxysilicon phthalocyanine

Cited by 21 publications

References 1 publication

Nitrogen isotopes in chlorophyll and the origin of Eastern Mediterranean sapropels

Nitrogen isotopes in chlorophyll and the origin of Eastern Mediterranean sapropels

Near-Infrared Fluorescence of Silicon Phthalocyanine Carboxylate Esters

Synthesis of dihydroxy silicon phthalocyanine tetrasulfonic acid and poly-μ-oxo silicon phthalocyanine tetrasulfonic acid

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