New Insights on the Interaction between Thiophene Derivatives and Au Surfaces. The Case of 3,4-Ethylenedioxythiophene and the Relevant Polymer

Terzi, Fabio; Pasquali, Luca; Montecchi, Monica; Nannarone, Stefano; Viinikanoja, Antti; Ääritalo, Timo; Salomäki, Mikko; Lukkari, Jukka; Doyle, Bryan P.; Seeber, Renato

doi:10.1021/jp203219b

Cited by 35 publications

(55 citation statements)

References 48 publications

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“…This lowerenergy peak originates from sulfur in broken thiophene units as C-S-Cu (thiolate) (the smaller doublet at 161.1 eV (violet curve) likely originates from atomically adsorbed sulfur). 50,52,53 By comparing the evolution of C 1s and S 2p spectra, we observe the complete rupture of the thiophene units between 200 and 300 C. A similar rupture of the thiophene unit in TTA has also been observed on Ni(111) in which case it leads to a cyclization reaction converting the desulfurized TTA into pentacene. 54…”

Section: Cu(111)supporting

confidence: 57%

Ullmann-type coupling of brominated tetrathienoanthracene on copper and silver

et al. 2014

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We report the synthesis of extended two-dimensional organic networks on Cu(111), Ag(111), Cu(110), and Ag(110) from thiophene-based molecules. A combination of scanning tunnelling microscopy and X-ray photoemission spectroscopy yields insight into the reaction pathways from single molecules towards the formation of two-dimensional organometallic and polymeric structures via Ullmann reaction dehalogenation and C-C coupling. The thermal stability of the molecular networks is probed by annealing at elevated temperatures of up to 500 °C. On Cu(111) only organometallic structures are formed, while on Ag(111) both organometallic and covalent polymeric networks were found to coexist. The ratio between organometallic and covalent bonds could be controlled by means of the annealing temperature. The thiophene moieties start degrading at 200 °C on the copper surface, whereas on silver the degradation process becomes significant only at 400 °C. Our work reveals how the interplay of a specific surface type and temperature steers the formation of organometallic and polymeric networks and describes how these factors influence the structural integrity of two-dimensional organic networks.

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Section: Cu(111)supporting

confidence: 57%

Ullmann-type coupling of brominated tetrathienoanthracene on copper and silver

et al. 2014

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“…The positions of the PEDOT Raman bands in presence and absence of FeT3ThP were used to verify that incorporation of the porphyrin monomer units into the polymer network occurs via co‐polymerization and not entrapment. Therefore, Raman spectra of EDOT, bi‐EDOT and tri‐EDOT in aqueous environment were simulated by DFT and are shown in the Supporting Information in Figure S3‐2, traces a‐c (for details regarding the simulation see section S3 in the Supporting Information) . Three distinct bands at 1417 cm −1 , 1499 cm −1 and 1587 cm −1 were obtained for mono‐EDOT, which were assigned to the vibrations observed at 1360 cm −1 , 1426 cm −1 and 1489 cm −1 in the experimental spectrum of EDOT in sodium phosphate buffer (Figure S3‐2, trace d, in the Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

Enhancement of the Electrocatalytic Activity of Thienyl‐Substituted Iron Porphyrin Electropolymers by a Hangman Effect

et al. 2018

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The thiophene‐modified iron porphyrin FeT3ThP and the respective iron Hangman porphyrin FeH3ThP, incorporating a carboxylic acid hanging group in the second coordination sphere of the iron center, were electropolymerized on glassy carbon electrodes using 3,4‐ethylenedioxythiophene (EDOT) as co‐monomer. Scanning electron microscopy images and Resonance Raman spectra demonstrated incorporation of the porphyrin monomers into a fibrous polymer network. Porphyrin/polyEDOT films catalyzed the reduction of molecular oxygen in a four‐electron reaction to water with onset potentials as high as +0.14 V vs. Ag/AgCl in an aqueous solution of pH 7. Further, FeT3ThP/polyEDOT films showed electrocatalytic activity towards reduction of hydrogen peroxide at highly positive potentials, which was significantly enhanced by introduction of the carboxylic acid hanging group in FeH3ThP. The second coordination sphere residue promotes formation of a highly oxidizing reaction intermediate, presumably via advantageous proton supply, as observed for peroxidases and catalases making FeH3ThP/polyEDOT films efficient mimics of heme enzymes.

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“…Samples for XPS analyses have been prepared according to a procedure previously reported 45 . All measurements were performed at room temperature.…”

Section: Methodsmentioning

confidence: 99%

Peptide nucleic acids tagged with four lysine residues for amperometric genosensors

Zanardi¹,

Terzi²,

Seeber³

et al. 2012

Artificial DNA: PNA & XNA

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A homothymine PNA decamer bearing four lysine residues has been synthesized as a probe for the development of amperometric sensors. On one hand, the four amino groups introduced make this derivative nine times more soluble than the corresponding homothymine PNA decamer and, on the other hand, allow the stable anchoring of this molecule on Au nanostructured surface through the terminal -NH2 moieties. In particular, XPS and electrochemical investigations performed with hexylamine, as a model molecule, indicate that the stable deposition of primary amine derivatives on such a nanostructured surface is possible and involves the free electron doublet on the nitrogen atom. This finding indicates that this PNA derivative is suitable to act as the probe molecule for the development of amperometric sensors. Thanks to the molecular probe chosen and to the use of a nanostructured surface as the substrate for the sensor assembly, the device proposed makes possible the selective recognition of the target oligonucleotide sequence with very high sensitivity.

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New Insights on the Interaction between Thiophene Derivatives and Au Surfaces. The Case of 3,4-Ethylenedioxythiophene and the Relevant Polymer

Cited by 35 publications

References 48 publications

Ullmann-type coupling of brominated tetrathienoanthracene on copper and silver

Ullmann-type coupling of brominated tetrathienoanthracene on copper and silver

Enhancement of the Electrocatalytic Activity of Thienyl‐Substituted Iron Porphyrin Electropolymers by a Hangman Effect

Peptide nucleic acids tagged with four lysine residues for amperometric genosensors

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