The chemisorption of polyimide precursors and related molecules on metal surfaces

Ashton, M.; Jones, T.S.; Richardson, N.V.; Mack, R. G.; Unertl, W. N.

doi:10.1016/0368-2048(90)80303-r

Cited by 25 publications

(9 citation statements)

References 15 publications

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“…There is already considerable evidence from vibrational spectroscopies, supported by X-ray photoemission, that room temperature adsorption of pyromellitic dianhydride, II , on a variety of surfaces, including Ag, , Ni, Cu, and Si, leads to loss of a CO unit and the resulting species has carboxylate character with which bonding to the substrate is effected in a bidentate, or more probably, a bridging manner. Our own previous EELS studies of phthalic anhydride adsorption on Cu{110} and Ni{110} surfaces agree with this conclusion. , We note, though, that adsorption onto the Pt{111} appears to be an exception, as PMDA has been found to adsorb intact on this surface. , Our previous studies were, however, limited to saturation exposure at room temperature. The coverage-dependent behavior, thermal evolution of the surface species, from 95 to 600 K, and stability of the various intermediates, as well as the influence of preadsorbed oxygen, are the subjects of this paper.…”

Section: Discussionmentioning

confidence: 99%

Anhydride Ring Chemistry at a Metal Surface

et al. 1998

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The adsorption of phthalic anhydride on clean and oxygen predosed Cu{110} surfaces has been studied by Fourier transform infrared spectroscopy in the temperature range 95−300 K. Further characterization of the adsorbed species and its thermal stability on these surfaces has been obtained from thermal desorption measurements. A variety of species are produced on the clean surface including the parent molecule, one in which the anhydride ring has been cleaved and one following the loss of a CO unit which is the stable form at room temperature. In the presence of oxygen, CO loss is prevented and, instead, a phthalate species is formed. Infrared spectroscopy is ideally suited to identify these species and their orientation, which varies both with coverage and temperature in a complex manner. Thermal breakdown of the molecule occurs above 530 K on the clean surface to produce a variety of gas-phase products including benzene. The breakdown occurs at a somewhat higher temperature (585 K) in the case of the oxygen-predosed surface and leads to an explosive release of the products into the gas phase.

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Section: Discussionmentioning

confidence: 99%

Anhydride Ring Chemistry at a Metal Surface

et al. 1998

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“…By tilting the two phenyl rings at approximately 15-20°to the surface plane around an axis which does not include either nitrogen atom, it is possible to bring the nitrogen of the upper ring to a similar height to that of the lower molecule thus making it possible for both nitrogens to be coordinated to the surface. Surface vibrational spectroscopy indicates that the phenyl ring is orientated close to parallel to the surface [28,29] but to date, these studies have concerned aniline reactions only with clean surfaces where the surface concentration of phenyl imide may not be high enough to force the formation of the pi-stacked complex.…”

Section: Discussionmentioning

confidence: 98%

“…It has been reported that the molecule dissociates at clean Cu(1 1 0) surfaces to give an amide (PhNH(a)) in which the phenyl ring lies approximately parallel to the surface [28,29]. The aim of the present work was to investigate whether the reaction of the amine group with oxygen was affected by the differing basicity of aniline from pyridine and ammonia and the steric hindrance of the phenyl ring.…”

Section: Introductionmentioning

confidence: 97%

Aromatic interactions in the close packing of phenyl-imides at Cu(110) surfaces

2004

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“…Discussion of PMDA Adsorption. The isolated PMDA molecule has a quasi-planar structure, close to D 2 h symmetry …”

Section: Adsorption Of Pyromellitic Dianhydridementioning

confidence: 99%

“…The isolated PMDA molecule has a quasi-planar structure, close to D 2h symmetry. 17 The strongest dipole active modes are associated with the stretching and bending modes of the anhydride groups. The symmetric (b 2u ) and asymmetric modes (b 1u ) of the ring C-O-C stretching vibrations are found at 1276 and 924 cm -1 , respectively.…”

Section: Adsorption Of Pmda On (2×1mentioning

confidence: 99%

Organic Beam Epitaxy Using Controlled PMDA−ODA Coupling Reactions on Cu{110}

Haq

Richardson

1999

J. Phys. Chem. B

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Reflection−absorption infrared spectroscopy (RAIRS) has been used to study in detail, as a function of temperature and coverage, the interaction of pyromellitic dianhydride (PMDA) and 4,4-oxydianiline (ODA) on the clean and oxygen-precovered Cu{110} surfaces. On the clean surface, both molecules show coverage-dependent reorientation from flat lying to upright species. The adsorption of PMDA on the clean surface leads to a ring-opening reaction of one of the anhydride group to produce a species with both carbonyl and carboxylate groups. The carbonyl group is lost into the gas phase above 350 K, with the resulting anhydride species bonded to the surface via the carboxylate group. The presence of preadsorbed oxygen also leads to the reaction of one of the anhydride groups, although in this case a dicarboxylate (phthalate) anhydride species is produced. The condensation reaction of 4,4-oxydianiline with the two PMDA-derived species has also been studied. It is shown that the PMDA−ODA oligomer can be grown layer by layer using controlled imide coupling reactions. The growth is monitored by IR spectroscopy.

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The chemisorption of polyimide precursors and related molecules on metal surfaces

Cited by 25 publications

References 15 publications

Anhydride Ring Chemistry at a Metal Surface

Anhydride Ring Chemistry at a Metal Surface

Aromatic interactions in the close packing of phenyl-imides at Cu(110) surfaces

Organic Beam Epitaxy Using Controlled PMDA−ODA Coupling Reactions on Cu{110}

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