Electrochemical metallization of self-assembled porphyrin monolayers

Nann, Thomas; Kielmann, Udo; Dietrich, Christoph F.

doi:10.1007/s00216-002-1342-7

Cited by 9 publications

(2 citation statements)

References 29 publications

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“…Oligo(phenyleneethynylene) (OPE) derivatives have attracted special interest due to their largely delocalized p-conjugated systems, resulting in a relatively high electrical conductivity along the molecular backbone. [1][2][3][4][5][6][7][8][9] By introducing a porphyrin as the tail group onto the OPE molecules, a wirelike molecule with optical and redox properties can be created and be of potential interest for application in solar cells, 10,11 sensors [12][13][14] and other optoelectronic devices. [15][16][17][18] The immobilization of the molecules on the electrode, e.g.…”

Section: Introductionmentioning

confidence: 99%

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A spectroscopic study of self-assembled monolayer of porphyrin-functionalized oligo(phenyleneethynylene)s on gold: the influence of the anchor moiety

Watcharinyanon

Nilsson

Moons

et al. 2008

Phys. Chem. Chem. Phys.

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Porphyrin-functionalized oligo(phenyleneethynylene)s (OPE) are promising molecules for molecular electronics applications. Three such molecules (1-3) with the common structure P-OPE-AG (P and AG are a porphyrin and anchor group, respectively) and different anchor groups, viz. an acetyl protected thiol, -S-COCH3 (1), an acetyl protected thiol with methylene linker, -CH2-S-COCH3 (2), and a trimethylsilylethynyl group, -C(triple bond)C-Si(CH3)3 (3) have been synthesized and the corresponding self-assembled monolayers (SAMs) on Au(111) substrates have been prepared. The integrity and structural properties of these films were studied by X-ray photoelectron spectroscopy and near-edge X-ray absorption fine structure spectroscopy. The results suggest that the films formed from 1 have a high orientational order with an almost upright orientation and dense packing of the molecular constituents, i.e. represent a high quality SAM. In contrast, molecule 2 formed disordered molecular layers on Au, even though the molecule-surface bonding (thiolate) is the same as in the case of molecule 1. This suggests that the methylene linker in molecule 2 has a strong impact on the quality of the resulting film, so that a well-ordered SAM cannot be formed. The silane system, 3, is also able to bind to the gold surface but the resulting SAM has a poor quality, being significantly disordered and/or comprised of strongly inclined molecules. The above results suggest that the nature of the anchor group along with a possible linker is an important parameter which, to a high extent, predetermines the entire quality of OPE-based molecular layers.

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Section: Introductionmentioning

confidence: 99%

“…The filtrate was concentrated to give the desired product as a yellowish solid. Flash chromatography (hexane/DCM, 2 : 3) yielded a solid which was recrystallized in hexane to afford 5 as a light red solid (12 Materials. Reagents and solvents were purchased from Acros and Aldrich and used without further purification.…”

Section: Introductionmentioning

confidence: 99%

A spectroscopic study of self-assembled monolayer of porphyrin-functionalized oligo(phenyleneethynylene)s on gold: the influence of the anchor moiety

Watcharinyanon

Nilsson

Moons

et al. 2008

Phys. Chem. Chem. Phys.

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Metal‐ion Binding to Self‐assembled Monolayers on Surfaces

Vaskevich

Rubinstein

2007

Encyclopedia of Electrochemistry

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The sections in this article are Introduction Binding of Metal Ions to Functionalized SAMs : General Phenomena and Case Studies Stoichiometry of Surface Metal‐organic Complexes Solution‐surface Equilibrium SAMs as Metal‐ion Receptors Ion Binding to SAMs : Direct Electrochemical Reporting Binding of Electrochemically Inert Ions: Reporting by Redox Reactions of Solution Species Binding of Electrochemically Inert Ions: Reporting by Redox Centers in the SAM Binding of Electrochemically Inert Ions: Application of Electrochemical Impedance Spectroscopy ( EIS ) Optical Methods for Control and Reporting of Ion Binding to SAMs Bilayers Formed by Metal‐organic Coordination Coordinated Organic Bilayers Immobilization of Biological Molecules through Coordination Binding Binding of Macrocycle Molecules

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Glycosyl‐Modified Diporphyrins for in Vitro and in Vivo Fluorescence Imaging

Liu

et al. 2013

ChemBioChem

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The application of probes for optical imaging is becoming popular as they have high safety and good biocompatibility. We prepared two kinds of glycosyl-modified diporphyrins, and their potentials as fluorescent probes were tested for the first time. After preparation of the glycosyl-modified porphyrin monomers, Ag-promoted coupling of the monomers was used to obtain glucose-modified porphyrin dimer (GPD) and lactose-modified porphyrin dimer (LPD). The strong interaction between the two porphyrin rings achieves red-shifted emission, and thus circumvents autofluorescence and light-scattering in biological samples. Although the glycosylation improves solubility, it also yielded selective attachment to cell membranes, and to chorions of early developmental-stage zebrafish. Patch-clamp experiments revealed the biocompatibility and low toxicity of GPD and LPD. Moreover, an in vivo imaging experiment provided direct evidence that zebrafish chorion contains sugar-binding proteins. The modification and derivatization make porphyrins potential bioimaging probes for specific optical imaging.

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Electrochemical metallization of self-assembled porphyrin monolayers

Cited by 9 publications

References 29 publications

A spectroscopic study of self-assembled monolayer of porphyrin-functionalized oligo(phenyleneethynylene)s on gold: the influence of the anchor moiety

A spectroscopic study of self-assembled monolayer of porphyrin-functionalized oligo(phenyleneethynylene)s on gold: the influence of the anchor moiety

Metal‐ion Binding to Self‐assembled Monolayers on Surfaces

Glycosyl‐Modified Diporphyrins for in Vitro and in Vivo Fluorescence Imaging

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