XSW feasibility study of CPh–OH on Ag(111): combining hard X-rays, low Z and, low coverage

Schulte, Karina; Woolley, Richard A. J.; Wang, L.; Moriarty, Philip; Birkett, P. R.; Kroto, Harold W.; Cowie, Bruce C. C.

doi:10.1016/j.nima.2005.05.026

Cited by 2 publications

(8 citation statements)

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“…The lack of observable 3 J FF coupling between the F atoms in the CF 2 and CF 3 moieties of a given C 2 F 5 group is not uncommon. 54,55 Furthermore, no such coupling was observed in the 19 F NMR spectra of C 1 -p,p,p-C 60 (C 2 F 5 ) 6 and C 1 -p 3 mp,p-C 60 (C 2 F 5 ) 8 . 32 The CF 2 multiplets of those two compounds were also very complex and have not yet been unambiguously assigned to specific F atoms in the CF 2 groups.…”

Section: Resultsmentioning

confidence: 98%

“…The 19 F NMR spectrum of C s -C 60 (C 2 F 5 ) 4 O consists of two sharp, equal-intensity singlets in the CF 3 region at δ -80.2 and -80.8 and a complex pattern of multiplets in the CF 2 region that extends from δ -108 to -112. The lack of observable 3 J FF coupling between the F atoms in the CF 2 and CF 3 moieties of a given C 2 F 5 group is not uncommon.…”

Section: Resultsmentioning

confidence: 99%

“…Atmosphericpressure chemical ionization (APCI) mass spectra were recorded on a Finnigan (ThermoQuest) LCQ DUO mass spectrometer (hexane or acetonitrile eluent, 0.3 mL min -1 flow rate). Samples for 19 F NMR spectroscopy were benzene-d6 solutions containing a small amount of hexafluorobenzene as an internal standard (δ -164.9). Spectra were recorded using a Varian INOVA-unity 400 spectrometer operating at 367.45 MHz.…”

Section: Methodsmentioning

confidence: 99%

“…Five of the X substituents are positioned on a para 5 ( p 5 ) loop of five edge-sharing p -C 6 X 2 hexagons, and the sixth substituent is positioned ortho to one and meta to two of the first five. There are only a few examples of isolable C 60 X 6 compounds with alternative structures, and these are C 60 H 6 , C 60 F 6 , C 60 (C(CH 3 )(CO 2 t -Bu) 2 ) 6 , a second isomer of C 60 Ph 5 (OH), , and C 1 -C 60 (CF 3 ) 6 . , The para 3 - meta - para ( p 3 mp ) ribbon of five edge-sharing C 6 (CF 3 ) 2 hexagons exhibited by the latter compound can be seen in its Schlegel diagram in Figure .

1 Schlegel diagrams for (top left to right) C s -C 60 (R f ) 4 O (R F = CF 3 , C 2 F 5 ), C s -C 60 (CF 3 ) 6 (the same structure as C 60 Br 6 , C 60 Cl 6 , and C 60 (CH 3 ) 6 ), C 1 - p 3 mp -C 60 (CF 3 ) 6 ; (middle left to right) C 5v -C 60 Ph 5 - , C s -C 60 F 8 , C 1 - p 3 mp , p -C 60 (CF 3 ) 8 ; (bottom left to right) C 2 -[ p 3 m 2 (loop)] 2 -C 60 (CF 3 ) 10 , C 1 -C 70 (CF 3 ) 16 , and C 1 -C 70 (CF 3 ) 18 .…”

Section: Introductionmentioning

confidence: 99%

“…Five of the X substituents are positioned on a para 5 (p 5 ) loop of five edge-sharing p-C 6 X 2 hexagons, and the sixth substituent is positioned ortho to one and meta to two of the first five. There are only a few examples of isolable C 60 X 6 compounds with alternative structures, and these are C 60 H 6 , 16 C 60 F 6 , 17 C 60 (C(CH 3 )(CO 2 t-Bu) 2 ) 6 , 18 a second isomer of C 60 Ph 5 -(OH), 13,19 and C 1 -C 60 (CF 3 ) 6 . 20,21 The para 3 -meta-para (p 3 mp) ribbon of five edge-sharing C 6 (CF 3 ) 2 hexagons exhibited by the latter compound can be seen in its Schlegel diagram in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

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Thermally Stable Perfluoroalkylfullerenes with the Skew-Pentagonal-Pyramid Pattern: C₆₀(C₂F₅)₄O, C₆₀(CF₃)₄O, and C₆₀(CF₃)₆

et al. 2006

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Reaction of C(60) with CF(3)I at 550 degrees C, which is known to produce a single isomer of C(60)(CF(3))(2,4,6) and multiple isomers of C(60)(CF(3))(8,10), has now been found to produce an isomer of C(60)(CF(3))(6) with the C(s)-C(60)X(6) skew-pentagonal-pyramid (SPP) addition pattern and an epoxide with the C(s)-C(60)X(4)O variation of the SPP addition pattern, C(s)-C(60)(CF(3))(4)O. The structurally similar epoxide C(s)-C(60)(C(2)F(5))(4)O is one of the products of the reaction of C(60) with C(2)F(5)I at 430 degrees C. The three compounds have been characterized by mass spectrometry, DFT quantum chemical calculations, Raman, visible, and (19)F NMR spectroscopy, and, in the case of the two epoxides, single-crystal X-ray diffraction. The compound C(s)-C(60)(CF(3))(6) is the first [60]fullerene derivative with adjacent R(f) groups that are sufficiently sterically hindered to cause the (DFT-predicted) lengthening of the cage (CF(3))C-C(CF(3)) bond to 1.60 A as well as to give rise to a rare, non-fast-exchange-limit (19)F NMR spectrum at 20 degrees C. The compounds C(s)-C(60)(CF(3))(4)O and C(s)-C(60)(C(2)F(5))(4)O are the first poly(perfluoroalkyl)fullerene derivatives with a non-fluorine-containing exohedral substituent and the first fullerene epoxides known to be stable at elevated temperatures. All three compounds demonstrate that the SPP addition pattern is at least kinetically stable, if not thermodynamically stable, at temperatures exceeding 400 degrees C. The high-temperature synthesis of the two epoxides also indicates that perfluoroalkyl substituents can enhance the thermal stability of fullerene derivatives with other substituents.

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Five of the X substituents are positioned on a para 5 (p 5 ) loop of five edge-sharing p-C 6 X 2 hexagons, and the sixth substituent is positioned ortho to one and meta to two of the first five. There are only a few examples of isolable C 60 X 6 compounds with alternative structures, and these are C 60 H 6 , 16 C 60 F 6 , 17 C 60 (C(CH 3 )(CO 2 t-Bu) 2 ) 6 , 18 a second isomer of C 60 Ph 5 -(OH), 13,19 and C 1 -C 60 (CF 3 ) 6 . 20,21 The para 3 -meta-para (p 3 mp) ribbon of five edge-sharing C 6 (CF 3 ) 2 hexagons exhibited by the latter compound can be seen in its Schlegel diagram in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

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Thermally Stable Perfluoroalkylfullerenes with the Skew-Pentagonal-Pyramid Pattern: C₆₀(C₂F₅)₄O, C₆₀(CF₃)₄O, and C₆₀(CF₃)₆

et al. 2006

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Theoretical and experimental comparison of SnPc, PbPc, and CoPc adsorption on Ag(111)

et al. 2010

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A combination of normal-incidence x-ray standing-wave ͑NIXSW͒ spectroscopy, x-ray photoelectron spectroscopy ͑XPS͒, scanning tunneling microscopy ͑STM͒, and density-functional theory ͑DFT͒ has been used to investigate the interaction of a number of phthalocyanine molecules ͑specifically, SnPc, PbPc, and CoPc͒ with the Ag͑111͒ surface. The metal-surface distances predicted by the DFT calculations for SnPc/Ag͑111͒ ͑2.48 Å͒ and CoPc/Ag͑111͒ ͑2.88 Å͒ are in good agreement with our NIXSW experimental results for these systems ͑2.31Ϯ 0.09 and 2.90Ϯ 0.05 Å, respectively͒. Good agreement is also found between calculated partial density-of-states plots and STM images of CoPc on Ag͑111͒. Although the DFT and Pb 4f NIXSW results for the Pb-Ag͑111͒ distance are similarly in apparently good agreement, the Pb 4f core-level data suggest that a chemical reaction between PbPc and Ag͑111͒ occurs due to the annealing procedure used in our experiments and that the similarity of the DFT and Pb 4f NIXSW values for the Pb-Ag͑111͒ distance is likely to be fortuitous. We interpret the Pb 4f XPS data as indicating that the Pb atom can detach from the PbPc molecule when it is adsorbed in the "Pb-down" position, leading to the formation of a Pb-Ag alloy and the concomitant reduction in Pb from a Pb 2+ state ͑in bulklike films of PbPc͒ to Pb 0 . In contrast to SnPc, neither PbPc nor CoPc forms a well-ordered monolayer on Ag͑111͒ via the deposition and annealing procedures we have used. Our DFT calculations show that each of the phthalocyanine molecules donate charge to the silver surface, and that back donation from Ag to the metal atom ͑Co, Sn, or Pb͒ is only significant for CoPc.

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XSW feasibility study of CPh–OH on Ag(111): combining hard X-rays, low Z and, low coverage

Cited by 2 publications

References 18 publications

Thermally Stable Perfluoroalkylfullerenes with the Skew-Pentagonal-Pyramid Pattern: C₆₀(C₂F₅)₄O, C₆₀(CF₃)₄O, and C₆₀(CF₃)₆

Thermally Stable Perfluoroalkylfullerenes with the Skew-Pentagonal-Pyramid Pattern: C₆₀(C₂F₅)₄O, C₆₀(CF₃)₄O, and C₆₀(CF₃)₆

Theoretical and experimental comparison of SnPc, PbPc, and CoPc adsorption on Ag(111)

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XSW feasibility study of CPh–OH on Ag(111): combining hard X-rays, low Z and, low coverage

Cited by 2 publications

References 18 publications

Thermally Stable Perfluoroalkylfullerenes with the Skew-Pentagonal-Pyramid Pattern: C60(C2F5)4O, C60(CF3)4O, and C60(CF3)6

Thermally Stable Perfluoroalkylfullerenes with the Skew-Pentagonal-Pyramid Pattern: C60(C2F5)4O, C60(CF3)4O, and C60(CF3)6

Theoretical and experimental comparison of SnPc, PbPc, and CoPc adsorption on Ag(111)

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Thermally Stable Perfluoroalkylfullerenes with the Skew-Pentagonal-Pyramid Pattern: C₆₀(C₂F₅)₄O, C₆₀(CF₃)₄O, and C₆₀(CF₃)₆

Thermally Stable Perfluoroalkylfullerenes with the Skew-Pentagonal-Pyramid Pattern: C₆₀(C₂F₅)₄O, C₆₀(CF₃)₄O, and C₆₀(CF₃)₆