Polyaminoquinone self-assembled films on electrodes: synthesis of all-organic molecular wires by solution phase epitaxy

Lukkari, Jukka; Kleemola, Kari; Meretoja, Minna; Kankare, Jouko

doi:10.1039/a701895i

Cited by 13 publications

(19 citation statements)

References 5 publications

(5 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition, quinones react readily with amines, which affords a feasible way of immobilizing various quinones on amino-terminated SAMs . We have recently demonstrated that long quinone-amine chains can be grown on 4-aminothiophenol-modified gold electrodes by repetitive self-assembly …”

Section: Introductionmentioning

confidence: 99%

Electrochemical Post-Self-Assembly Transformation of 4-Aminothiophenol Monolayers on Gold Electrodes

et al. 1998

Self Cite

View full text Add to dashboard Cite

Electrochemical oxidation of a self-assembled monolayer (SAM) of 4-aminothiophenol on polycrystalline gold electrodes leads to a complex voltammetric behavior characterized by an initial irreversible oxidation at ∼+0.77 V versus SSCE (sodium saturated calomel electrode) and the formation of a pseudostable surface redox couple at +0.53 V. The oxidized form of this couple is hydrolyzed in acidic solutions to another redox pair with the formal redox potential of ∼+0.3 V. We show that the oxidation leads to a radical−radical coupling reaction between two adjacent aminothiophenol molecules, yielding an electrode surface modified with 4‘-mercapto-4-aminodiphenylamine, the thiol derivative of a head-to-tail aniline dimer. The oxidized form of the dimer, quinone diimine, undergoes hydrolysis to the corresponding quinone monoimine and, eventually, to the original surface-bound 4-aminothiophenol and benzoquinone. The mechanism of the monolayer oxidation reaction has been elucidated by a variety of electrochemical and spectroelectrochemical techniques together with electrochemical data obtained with a soluble model compound, 4-(methylthio)aniline. In addition, X-ray photoelectron spectroscopy (XPS) characterization of the 4-aminothiophenol (Au−SPhNH2), the 2-(4‘-mercaptophenylamino)benzoquinone (Au−SPhNH−BQ), and the oxidized 4-aminothiophenol SAMs is reported. The formation of an electrode surface modified with aniline dimers explains the beneficial effect that 4-aminothiophenol SAM exhibits in the electrochemical polymerization of aniline. We suggest that it favors the direct addition of aniline monomers to the oligomer chains on the surface, which results in a more ordered structure compared with the deposition of oligomers from the solution. This result is very important for the preparation of highly ordered polyaniline films for advanced applications in molecular electronics and sensor technology. The results also show that after the initial dimerization step, aniline polymerization can proceed through coupling of the neutral monomer to the oxidized oligomer.

show abstract

Section: Introductionmentioning

confidence: 99%

Electrochemical Post-Self-Assembly Transformation of 4-Aminothiophenol Monolayers on Gold Electrodes

et al. 1998

Self Cite

View full text Add to dashboard Cite

show abstract

“…Natural and synthetic quinone–amine polymers have received considerable attention due to their unique properties and potential applications in various technical fields such as conducting materials, corrosion inhibitors for mild steels, and coating materials 1–6. Three kinds of novel poly(aromatic amino‐2,3‐pyridinedione) oligomers, including poly(4,4′‐methylenedianiline–2,3‐pyridinedione, PMDAP), poly(4,4′‐ethylene dianiline–2,3‐pyridinedione, PEDAP), and poly(4,4′‐sulfonyldianiline–2,3‐pyridinedione, PSDAP), have been synthesized by our cooperative work group.…”

Section: Methodsmentioning

confidence: 99%

Characterization of novel poly(aromatic amine‐2,3‐pyridinedione) oligomers by matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry

Deng¹,

Zhang²,

Deng³

et al. 2003

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

“…(2,3) They are also involved in photosynthesis, (4,5) and they are electroactive molecular surfactants used in Langmuir-Blodgett films. (6,7) In addition, they are present in many biological systems such as vitamin K 1 or K 3 and the quinone group appears frequently in the structure a To whom correspondence should be addressed (E-mail: p.jimenez@iqfr.csic.es).…”

Section: Introductionmentioning

confidence: 99%

Thermochemistry of 9-hydroxy-1,4-anthraquinone and 9-methoxy-1,4-anthraquinone

Jiménez

Roux

Dávalos

et al. 2002

The Journal of Chemical Thermodynamics

View full text Add to dashboard Cite

Polyaminoquinone self-assembled films on electrodes: synthesis of all-organic molecular wires by solution phase epitaxy

Cited by 13 publications

References 5 publications

Electrochemical Post-Self-Assembly Transformation of 4-Aminothiophenol Monolayers on Gold Electrodes

Electrochemical Post-Self-Assembly Transformation of 4-Aminothiophenol Monolayers on Gold Electrodes

Characterization of novel poly(aromatic amine‐2,3‐pyridinedione) oligomers by matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry

Thermochemistry of 9-hydroxy-1,4-anthraquinone and 9-methoxy-1,4-anthraquinone

Contact Info

Product

Resources

About