Irreversible self-assembly of monomolecular layers of a cobalt(II) hexadecyltetrapyridylporphyrin amphiphile at gold electrodes and its catalysis of oxygen reduction

Galen, Dean A. Van; Majda, Marcin

doi:10.1021/ac00166a015

Cited by 46 publications

(40 citation statements)

References 25 publications

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“…The CoTPP molecule (19 Å) [40] is approximately four times larger than 4-ATP (4.3 Å) so at least eight molecules of 4-ATP should be covered by one CoTPP. This also agrees with the literature that proposed that CoTPP spontaneously adsorbed with a flat lying orientation [17] and Van Galen and Majda have also found a parallel orientation when chemisorbing porphyrin via a hexadecyl carbon chain on gold substrate [13].…”

Section: Monolayer Characterizationsupporting

confidence: 92%

See 1 more Smart Citation

An electrochemical and spectroelectrochemical study of pentacoordinated CoTPP on glassy carbon electrode

Paz¹,

Médard²,

Morin³

2010

Journal of Electroanalytical Chemistry

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Section: Monolayer Characterizationsupporting

confidence: 92%

“…Numerous studies [10][11][12][13][14][15][16][17] on self assembled monolayer (SAM) of porphyrins on gold have been reported. Such organisations facilitate the electron transfer from the substrate to the porphyrin.…”

Section: Introductionmentioning

confidence: 99%

An electrochemical and spectroelectrochemical study of pentacoordinated CoTPP on glassy carbon electrode

Paz¹,

Médard²,

Morin³

2010

Journal of Electroanalytical Chemistry

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“…1,6 Several different Porphyrin monolayer coverage 507 have done for cobalt 5,10,15,20-tetra(4-pyridyl)porphyrin (CoTPyP) monolayers. 20 They used a simple square, with the sides defined by the maximum length of CoTPyP, as their basis for the porphyrin ring. They predict 4.2 ð 10 13 molecules cm 2 for the parallel arrangement and 20 ð 10 13 molecules cm 2 for the perpendicular arrangement of CoTPyP molecules ( Table 1), indicating that porphyrins in the face-to-face arrangement pack with a significantly higher density than those in a side-by-side arrangement.…”

Section: Introductionmentioning

confidence: 99%

“…They predict 4.2 ð 10 13 molecules cm 2 for the parallel arrangement and 20 ð 10 13 molecules cm 2 for the perpendicular arrangement of CoTPyP molecules ( Table 1), indicating that porphyrins in the face-to-face arrangement pack with a significantly higher density than those in a side-by-side arrangement. 20 Researchers working with a variety of porphyrin monolayers have experimentally determined surface concentrations. Shimazu et al prepared two similar porphyrins-Zn(II) 5-[p-(6-mercaptohexoxy)-phenyl]-10,15,20-triphenylporphyrin (ZnP1S) and Zn(II) 5,10,15,20-tetrakis-[p-(6-mercaptohexoxy)phenyl]porphyrin (ZnP4S)-that are believed to align on a gold surface in a parallel (side-byside, ZnP4S) or perpendicular (face-to-face, ZnP1S) manner.…”

Section: Introductionmentioning

confidence: 99%

Determination of surface coverage for tetraphenylporphyrin monolayers using ultraviolet visible absorption and x‐ray photoelectron spectroscopies

Bramblett

Boeckl

Hauch

et al. 2002

Surface & Interface Analysis

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The surface coverage of thiolated tetraphenylporphyrin derivatives assembled on gold has been determined using ultraviolet/visible absorption spectroscopy (UV/Vis) and x-ray photoelectron spectroscopy (XPS). Ultraviolet/visible absorption spectroscopy was used to calculate the surface concentration of porphyrin molecules through two independent approaches: the first measured the porphyrin concentration in solution after the displacement of a porphyrin monolayer from the gold surface; and the second directly exploited the absorptivity of the monolayers. Furthermore, we determined experimentally the extinction coefficients for the porphyrin monolayers and verified that the extinction coefficients are in agreement with a simple theoretical model that is frequently applied to porphyrin monolayers. Two separate models, both based on a uniform overlayer, were applied to the XPS data to determine the surface concentration of the porphyrin monolayers. Finally, for comparison of the UV/Vis and XPS results, a model of an ordered tetraphenylporphyrin arrangement on a surface was utilized to calculate coverage. The results of these two spectroscopic techniques differed by as much as a factor of 4, but they were generally comparable to those for related porphyrin systems. Determination of the surface coverage of monolayers is often challenging, thus the comparison of two independent experimental techniques allows for a more accurate estimation of monolayer coverage, and demonstrates the often unrealized potential to calculate the coverage of organic monolayers using XPS.

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“…Moreover, the porphyrin framework is readily modified to adjust electronic and structural parameters. For this reason, the immobilization of metalloporphyrins at electrode surfaces for the electrocatalysis of dioxygen reduction has received significant attention [7,8]. The bulk of this previous work involves the physical adsorption of active metalloporphyrin complexes on pyrolytic graphite, glassy carbon or gold electrodes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Thiol-Derivatized Porphyrins and Metalloporphyrin complexes

Yuan

Woo

1997

J. Porphyrins Phthalocyanines

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A series of thiol-derivatized porphyrins and the corresponding cobalt and zinc complexes were synthesized from 5-(p-aminophenyl)-10,15,20-triphenylporphyrin ( H 2 TPP - NH 2), and 5α,15α-bis(o-aminophenyl)porphyrin ( H 2 DPE - ( NH 2)2). These derivatized porphyrins have a different number of thiol appendages attached via amide linkages at different locations. The thiol-derivatized porphyrins made from H 2 TPP - NH 2, H 2 TPP - NHC ( O )( CH 2) n SH ( n = 2, 4, 5, 10), have one alkyl-thiol appendage attached to the porphyrin through an amide linkage on the p-aminophenyl position. The derivatives made from H 2 DPE -( NH 2)2 have two alkyl-thiol appendages attached to the porphyrin through amide linkages on the o-aminophenyl positions on the same face of the porphyrin ring. These thiol-derivatized porphyrins are important adsorbates for the preparation of thiol–porphyrin monolayers on gold.

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Irreversible self-assembly of monomolecular layers of a cobalt(II) hexadecyltetrapyridylporphyrin amphiphile at gold electrodes and its catalysis of oxygen reduction

Cited by 46 publications

References 25 publications

An electrochemical and spectroelectrochemical study of pentacoordinated CoTPP on glassy carbon electrode

An electrochemical and spectroelectrochemical study of pentacoordinated CoTPP on glassy carbon electrode

Determination of surface coverage for tetraphenylporphyrin monolayers using ultraviolet visible absorption and x‐ray photoelectron spectroscopies

Synthesis and Characterization of Thiol-Derivatized Porphyrins and Metalloporphyrin complexes

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