Orientation and bonding of benzoic acid, phthalic anhydride and pyromellitic dianhydride on Cu(110)

Frederick, B.G.; Ashton, M.; Richardson, N.V.; Jones, T.S.

doi:10.1016/0039-6028(93)90388-z

Cited by 82 publications

(36 citation statements)

References 30 publications

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“…As a consequence, the precise analysis presented here might be very useful for the comprehension of other supramolecular systems at surfaces, particularly for those involving carboxylic functional groups. [6][7][8]10,24 …”

Section: Discussionmentioning

confidence: 99%

Hydrogen and Coordination Bonding Supramolecular Structures of Trimesic Acid on Cu(110)

Claßen

Lingenfelder²,

Wang³

et al. 2007

J. Phys. Chem. A

119

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The adsorption of trimesic acid (TMA) on Cu(110) has been studied in the temperature range between 130 and 550 K and for coverages up to one monolayer. We combine scanning tunneling microscopy (STM), low-energy electron diffraction (LEED), reflection absorption infrared spectroscopy (RAIRS), X-ray photoemission spectroscopy (XPS), and density functional theory (DFT) calculations to produce a detailed adsorption phase diagram for the TMA/Cu(110) system as a function of the molecular coverage and the substrate temperature. We identify a quite complex set of adsorption phases, which are determined by the interplay between the extent of deprotonation, the intermolecular bonding, and the overall energy minimization. For temperatures up to 280 K, TMA molecules are only partly deprotonated and form hydrogen-bonded structures, which locally exhibit organizational chirality. Above this threshold, the molecules deprotonate completely and form supramolecular metal-organic structures with Cu substrate adatoms. These structures exist in the form of single and double coordination chains, with the molecular coverage driving distinct phase transitions.

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Section: Discussionmentioning

confidence: 99%

Hydrogen and Coordination Bonding Supramolecular Structures of Trimesic Acid on Cu(110)

Claßen

Lingenfelder²,

Wang³

et al. 2007

J. Phys. Chem. A

119

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“…New generation spectrometers are currently producing instrumental resolutions better than 1 meV (ϳ 8 cm Ϫ1 ). 13,14,30 Frederick et al 31 discuss and evaluate various methods of analysis. 24 Despite substantial instrument resolution improvements, there may still be a limitation in assigning the vibrational modes of complex polymeric molecules and identifying modes associated with surface orientation, crystallinity, and chemical modification.…”

Section: Spectral Resolutionmentioning

confidence: 99%

High-resolution electron energy loss spectroscopy and infrared spectroscopy of polymer surfaces: High-resolution and orientation effects of polytetrafluoroethylene films

Akavoor

Menezes²,

Kesmodel

et al. 1996

Journal of Vacuum Science &Amp; Technology A: Vacuum, Surfaces, and Films

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Articles you may be interested inSurface structure of 3C-SiC(111) fabricated by C60 precursor: A scanning tunneling microscopy and high resolution electron energy loss spectroscopy study Application of highresolution electron energy loss spectroscopy to the adsorption and the photoreaction of CH2I2 and CD3OD on a MoO x thin film J. Vac. Sci. Technol. A 13, 2689 (1995); 10.1116/1.579469Hydrogen and CO spillover at Cu/Rh(100) bimetallic surfaces studied by highresolution electron energyloss spectroscopy J.The vibrational structure of oriented polytetrafluoroethylene has been studied using high-resolution electron energy loss spectroscopy ͑HREELS͒ and infrared spectroscopy. Record-high resolutions of 6 -15 cm Ϫ1 in HREELS with a state-of-the-art spectrometer are reported. Selection rules and orientation effects probed by the two different spectroscopies are discussed and comparisons are made between surface and bulk structure. Resonance electron scattering in HREELS has been used to study orientation effects of an intense Raman-active ͑C-C͒ mode at 730 cm Ϫ1 . The resonance seen in HREELS is identified as the *͑C-C͒ state. HREELS results have been related to near-edge x-ray absorption fine structure results. We discuss several future improvements that need to be addressed if ultrahigh resolution EELS is to become a more applicable and powerful tool for the study of polymer surfaces.

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“…Each of these processes can be triggered through thermal activation . On reactive surfaces, the presence of carboxylic acid can affect the adsorption geometry of small molecules because the molecule can deprotonate on deposition and the molecular plane can be oriented upright or tilt with respect to the substrate. ,− Benzoic acid, a simple monocarboxylic acid, deprotonates upon adsorption on copper surfaces and assumes an upright configuration with respect to the surface, that is, the molecules are oriented with their phenyl rings perpendicular to the substrate. − This adsorption geometry arises from the strong carboxylate–copper interaction . The addition of more than one carboxylic group to a molecule introduces some complication to this scenario owing to competition between substrate–molecule (copper–carboxylate) and molecule–molecule interactions. ,, For example, the copper–carboxylate interaction suppresses hydrogen bonding between molecules in terephthalic acid (TPA), a dicarboxylated phenyl, because TPA adsorbs in a perpendicular orientation with respect to the Cu(110) surface .…”

Section: Introductionmentioning

confidence: 99%

Adsorption, Deprotonation, and Decarboxylation of Isophthalic Acid on Cu(111)

et al. 2019

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The surface-assisted reaction of rationally designed organic precursors is an emerging approach toward fabricating atomically precise nanostructures. Recently, on-surface decarboxylation has attracted attention due to its volatile by-products, which tend to leave the surface during the reaction means only the desired products are retained on the surface. However, in addition to acting as the reactive site, the carboxylic acid groups play a vital role in the adsorption configuration of small-molecule molecular precursors and therefore in the reaction pathways. Here, scanning tunnelling microscopy (STM), synchrotron radiation photoelectron spectroscopy (SRPES), and near-edge X-ray absorption fine structure (NEXAFS) spectroscopy have been employed to characterize the monodeprotonated, fully deprotonated, and decarboxylated products of isophthalic acid (IPA) on Cu(111). IPA is partially reacted (monodeprotonated) upon adsorption on Cu(111) at room temperature. Angular-dependent X-ray photoelectron spectroscopy reveals that IPA initially anchors to the surface via the carboxylate group. After annealing, the molecule fully deprotonates and reorients so that it anchors to the surface via both carboxylate groups in a bipodal configuration. NEXAFS confirms that the molecule is tilted upon adsorption and after full deprotonation. Following decarboxylation, the flat-lying molecule forms into oligomeric motifs on the surface. This work demonstrates the importance of molecular adsorption geometry for on-surface reactions.

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Orientation and bonding of benzoic acid, phthalic anhydride and pyromellitic dianhydride on Cu(110)

Cited by 82 publications

References 30 publications

Hydrogen and Coordination Bonding Supramolecular Structures of Trimesic Acid on Cu(110)

Hydrogen and Coordination Bonding Supramolecular Structures of Trimesic Acid on Cu(110)

High-resolution electron energy loss spectroscopy and infrared spectroscopy of polymer surfaces: High-resolution and orientation effects of polytetrafluoroethylene films

Adsorption, Deprotonation, and Decarboxylation of Isophthalic Acid on Cu(111)

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