Growth and characterization of benzylic amide [2]catenane thin films

Fustin, Charles‐André; Rudolf, Petra; Taminiaux, A.F.; Zerbetto, Francesco; Leigh, David A.; Caudano, R.

doi:10.1016/s0040-6090(98)00653-1

Cited by 22 publications

(31 citation statements)

References 12 publications

(22 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Upon comparison with the solid state infrared data and a previous HREELS study of benzylic amide [2] catenane adsorbed on Au 1 1 1, the main vibrational bands of the parent compound can be identi®ed with the exception of the N±H stretching mode expected at $3330 cm À1 [15,16,21,22]. The absence of this band is not surprising given the predicted low intensity of this energy loss and its close proximity to the C±H stretching region [15,23,24]. The presence of aliphatic and aromatic groups is indicated by the intense feature at 740 cm À1 , which is unambiguously assigned to out-of-plane C±H deformations (c CH ) of the phenyl rings, and the occurrence of C±H in-plane stretching (m CH ) at 2920 cm À1 .…”

Section: Identi®cation Of the Adsorbed Surface Speciesmentioning

confidence: 90%

“…To this end, the formation and characterisation of two-dimensional ordered arrays of these molecules on solid supports such that they retain their dynamic properties may prove rewarding. Fustin et al have previously studied the adsorption of benzylic amide [2] catenane on Au(1 1 1) [15,16]. The authors report chemisorption of the molecule via the carbonyl moiety of the amide groups at low coverage and a substrate template eect resulting in well-ordered ®lms extending for the very ®rst layers.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

A high resolution electron energy loss spectroscopy study of the adsorption of benzylic amide macrocycle on Au(111)

et al. 2001

View full text Add to dashboard Cite

The adsorption from the gas phase of a macrocyclic molecule composed of benzylic amide (±CONH±CH 2 ±C 6 H 4 ±) groups on Au(1 1 1) at 300 K has been studied using high resolution electron energy loss spectroscopy. The ®lm order and vibrational properties were explored as a function of coverage, method of adlayer deposition and annealing. Beyond a critical coverage, a template eect strongly in¯uences the macrocycleÕs orientation with respect to the substrate. In the case of ordered ®lms (domain size > 80 A), the intensity of the out-of-plane C±H deformation mode relative to the in-plane C±H stretch indicates that an adsorption geometry with the plane of the phenyl rings largely parallel to the Au(1 1 1) surface is favoured in the submonolayer to monolayer coverage regime. Upon consideration of solid state Xray diraction data, this¯at-lying molecular orientation, which is accompanied by chemisorption via the carbonyl function, must involve considerable distortion of the adsorbed macrocycle from its crystal structure.

show abstract

Section: Identi®cation Of the Adsorbed Surface Speciesmentioning

confidence: 90%

Section: Introductionmentioning

confidence: 99%

A high resolution electron energy loss spectroscopy study of the adsorption of benzylic amide macrocycle on Au(111)

et al. 2001

View full text Add to dashboard Cite

show abstract

“…The spectra contain the vibrational bands expected upon comparison with solid-state infrared data and a previous HREELS study of a benzylic amide [2]catenane adsorbed on Au(111). 42,47 The prominent vibrational peak observed at 740 cm -1 is unambiguously assigned to out-of-plane C-H deformations (γ CH ) characteristic of the phenyl rings. 48,49 The corresponding C-H in-plane stretching (ν CH ) is identified as the highest energy loss at 2920 cm -1 and includes contributions from the aliphatic groups.…”

Section: High-resolution Electron Energy Loss Spectroscopymentioning

confidence: 98%

“…Similarly, HREELS studies of formic acid and [2]catenane adsorption on Au(111), report the occurrence of a Au-O stretching vibration at 480 and 484 cm -1 , respectively. 42,52,53 The adsorption geometry of the macrocycle and hence additional information on the nature of surface chemical bonding was obtained by performing off-specular scattering studies and utilizing the metal surface dipole selection rule (MSSR). The selection rule in HREELS applies to specular (dipole) scattering of electrons from molecules adsorbed on a metal surface which effectively screens dynamic dipole moments oriented parallel to the surface such that only those vibrations with a component of the dipole moment change normal to the surface may be observed.…”

Section: High-resolution Electron Energy Loss Spectroscopymentioning

confidence: 99%

Adsorption of a Benzylic Amide Macrocycle on a Solid Substrate: XPS and HREELS Characterization of Thin Films Grown on Au(111)

et al. 2002

View full text Add to dashboard Cite

Thin films of a benzylic amide macrocycle, the common component of a wide class of mechanically interlocked molecules, are prepared by vapor deposition on Au(111). The films are characterized by monochromated X-ray photoelectron spectroscopy (XPS) and high resolution electron energy loss spectroscopy (HREELS). The relative amounts of carbon, nitrogen, and oxygen are consistent with the formation of intact molecular species. At monolayer coverage, the relative intensity of out-of-plane to in-plane phenyl ring vibrational modes indicates that the macrocycle adopts a nearly flat-lying conformation. The formation of a chemisorption bond is evidenced by the presence of a Au-O stretching vibration and a low binding energy component in the O 1s core level region assigned to interfacial bonding. A decrease in film order and the absence of a preferred molecular orientation is observed at higher coverages. Computer modeling of the adsorption of the macrocycle on the surface rationalizes the experimental observations.

show abstract

“…The solid-state infrared data is presented as an inset for comparison. Previous HREELS studies of benzylic amide macrocycle 33 and benzylic amide ͓2͔catenane adsorbed on Au͑111͒ 34 and infrared reflection absorption spectroscopy data for benzylic amide ͓2͔catenane adsorbed on Au͑111͒ 35 are also taken into account for the assignment of the energy losses.…”

Section: High-resolution Electron-energy-loss Spectroscopymentioning

confidence: 99%

Experimental and theoretical study of the adsorption of fumaramide [2]rotaxane on Au(111) and Ag(111) surfaces

Mendoza

Whelan

Jalkanen

et al. 2005

The Journal of Chemical Physics

View full text Add to dashboard Cite

Link to publication in University of Groningen/UMCG research database Citation for published version (APA): Mendoza, S. M., Whelan, C. M., Jalkanen, J-P., Zerbetto, F., Gatti, F., Kay, E. R., ... Rudolf, P. (2005 Thin films of fumaramide ͓2͔rotaxane, a mechanically interlocked molecule composed of a macrocycle and a thread in a "bead and thread" configuration, were prepared by vapor deposition on both Ag͑111͒ and Au͑111͒ substrates. X-ray photoelectron spectroscopy ͑XPS͒ and high-resolution electron-energy-loss spectroscopy were used to characterize monolayer and bulklike multilayer films. XPS determination of the relative amounts of carbon, nitrogen, and oxygen indicates that the molecule adsorbs intact. On both metal surfaces, molecules in the first adsorbed layer show an additional component in the C 1s XPS line attributed to chemisorption via amide groups. Molecular-dynamics simulation indicates that the molecule orients two of its eight phenyl rings, one from the macrocycle and one from the thread, in a parallel bonding geometry with respect to the metal surfaces, leaving three amide groups very close to the substrate. In the case of fumaramide ͓2͔rotaxane adsorption on Au͑111͒, the presence of certain out-of-plane phenyl ring and Au-O vibrational modes points to such bonding and a preferential molecular orientation. The theoretical and experimental results imply that the three-dimensional intermolecular configuration permits chemisorption at low coverage to be driven by interactions between the three amide functions of fumaramide ͓2͔rotaxane and the Ag͑111͒ or Au͑111͒ surface.

show abstract

Growth and characterization of benzylic amide [2]catenane thin films

Cited by 22 publications

References 12 publications

A high resolution electron energy loss spectroscopy study of the adsorption of benzylic amide macrocycle on Au(111)

A high resolution electron energy loss spectroscopy study of the adsorption of benzylic amide macrocycle on Au(111)

Adsorption of a Benzylic Amide Macrocycle on a Solid Substrate: XPS and HREELS Characterization of Thin Films Grown on Au(111)

Experimental and theoretical study of the adsorption of fumaramide [2]rotaxane on Au(111) and Ag(111) surfaces

Contact Info

Product

Resources

About