Structure of and competitive adsorption in alkyl dicarbamate two-dimensional crystals

Journal of the American Chemical Society

Volumn 127, Issue 13, 2005, Pages 4879-4887

  Kim, Kibum ^a   Plass, Katherine E ^a   Matzger, Adam J ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION; CARBON; CRYSTAL STRUCTURE; FUNCTIONAL POLYMERS; HYDROGEN BONDS; MECHANICAL PROPERTIES; MELTING; OLIGOMERS; SCANNING TUNNELING MICROSCOPY; X RAY DIFFRACTION ANALYSIS;

ALKYL DICARBAMATE; FUNCTIONAL MATERIALS; MATERIAL PROPERTIES; OLIGOURETHANE SURFACE COATINGS;

SINGLE CRYSTALS;

ALKANE; ALKYL GROUP; CARBAMIC ACID DERIVATIVE;

ADSORPTION; ARTICLE; BINDING COMPETITION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DENSITY; GEOMETRY; HYDROGEN BOND; MATERIALS TESTING; MATHEMATICAL COMPUTING; MELTING POINT; OLIGOMERIZATION; POLYMERIZATION; SCANNING TUNNELING MICROSCOPY; SURFACE PROPERTY; THREE DIMENSIONAL IMAGING; X RAY DIFFRACTION;

EID: 16844383131     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja043028+     Document Type: Article

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68. Phase separation is typically observed in competitive adsorption of two molecules that are significantly different in packing geometry. This phenomenon results from the loss of intermolecular interaction when two different adsorbates are neighboring in a molecular column. By contrast, if the two adsorbates possess very similar packing structures, random mixing occurs. See: Yablon, D. G.; Ertas, D.; Fang, H. B.; Flynn, G. W. Isr. J. Chem. 2003, 43, 383-392. Stevens, F.; Beebe, T. P. Langmuir 1999, 15, 6884-6889. Yablon, D. G.; Wintgens, D.; Flynn, G. W. J. Phys. Chem. B 2002, 106, 5470-5475. Gesquière, A.; De Feyter, S.; De Schryver, F. C.; Schoonbeek, F.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Nano Lett. 2001, 1, 201-206. Cousty, J.; Van, L. P. Phys. Chem. Chem. Phys. 2003, 5, 599-603. Padowitz, D. F.; Messmore, B. W. J. Phys. Chem. B 2000, 104, 9943-9946. Ohshiro, T.; Ito, T.; Buhlmann, P.; Umezawa, Y. Anal. Chem. 2001, 73, 878-883.
69. Phase separation is typically observed in competitive adsorption of two molecules that are significantly different in packing geometry. This phenomenon results from the loss of intermolecular interaction when two different adsorbates are neighboring in a molecular column. By contrast, if the two adsorbates possess very similar packing structures, random mixing occurs. See: Yablon, D. G.; Ertas, D.; Fang, H. B.; Flynn, G. W. Isr. J. Chem. 2003, 43, 383-392. Stevens, F.; Beebe, T. P. Langmuir 1999, 15, 6884-6889. Yablon, D. G.; Wintgens, D.; Flynn, G. W. J. Phys. Chem. B 2002, 106, 5470-5475. Gesquière, A.; De Feyter, S.; De Schryver, F. C.; Schoonbeek, F.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Nano Lett. 2001, 1, 201-206. Cousty, J.; Van, L. P. Phys. Chem. Chem. Phys. 2003, 5, 599-603. Padowitz, D. F.; Messmore, B. W. J. Phys. Chem. B 2000, 104, 9943-9946. Ohshiro, T.; Ito, T.; Buhlmann, P.; Umezawa, Y. Anal. Chem. 2001, 73, 878-883.
70. Phase separation is typically observed in competitive adsorption of two molecules that are significantly different in packing geometry. This phenomenon results from the loss of intermolecular interaction when two different adsorbates are neighboring in a molecular column. By contrast, if the two adsorbates possess very similar packing structures, random mixing occurs. See: Yablon, D. G.; Ertas, D.; Fang, H. B.; Flynn, G. W. Isr. J. Chem. 2003, 43, 383-392. Stevens, F.; Beebe, T. P. Langmuir 1999, 15, 6884-6889. Yablon, D. G.; Wintgens, D.; Flynn, G. W. J. Phys. Chem. B 2002, 106, 5470-5475. Gesquière, A.; De Feyter, S.; De Schryver, F. C.; Schoonbeek, F.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Nano Lett. 2001, 1, 201-206. Cousty, J.; Van, L. P. Phys. Chem. Chem. Phys. 2003, 5, 599-603. Padowitz, D. F.; Messmore, B. W. J. Phys. Chem. B 2000, 104, 9943-9946. Ohshiro, T.; Ito, T.; Buhlmann, P.; Umezawa, Y. Anal. Chem. 2001, 73, 878-883.
71. Phase separation is typically observed in competitive adsorption of two molecules that are significantly different in packing geometry. This phenomenon results from the loss of intermolecular interaction when two different adsorbates are neighboring in a molecular column. By contrast, if the two adsorbates possess very similar packing structures, random mixing occurs. See: Yablon, D. G.; Ertas, D.; Fang, H. B.; Flynn, G. W. Isr. J. Chem. 2003, 43, 383-392. Stevens, F.; Beebe, T. P. Langmuir 1999, 15, 6884-6889. Yablon, D. G.; Wintgens, D.; Flynn, G. W. J. Phys. Chem. B 2002, 106, 5470-5475. Gesquière, A.; De Feyter, S.; De Schryver, F. C.; Schoonbeek, F.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Nano Lett. 2001, 1, 201-206. Cousty, J.; Van, L. P. Phys. Chem. Chem. Phys. 2003, 5, 599-603. Padowitz, D. F.; Messmore, B. W. J. Phys. Chem. B 2000, 104, 9943-9946. Ohshiro, T.; Ito, T.; Buhlmann, P.; Umezawa, Y. Anal. Chem. 2001, 73, 878-883.
72. Phase separation is typically observed in competitive adsorption of two molecules that are significantly different in packing geometry. This phenomenon results from the loss of intermolecular interaction when two different adsorbates are neighboring in a molecular column. By contrast, if the two adsorbates possess very similar packing structures, random mixing occurs. See: Yablon, D. G.; Ertas, D.; Fang, H. B.; Flynn, G. W. Isr. J. Chem. 2003, 43, 383-392. Stevens, F.; Beebe, T. P. Langmuir 1999, 15, 6884-6889. Yablon, D. G.; Wintgens, D.; Flynn, G. W. J. Phys. Chem. B 2002, 106, 5470-5475. Gesquière, A.; De Feyter, S.; De Schryver, F. C.; Schoonbeek, F.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Nano Lett. 2001, 1, 201-206. Cousty, J.; Van, L. P. Phys. Chem. Chem. Phys. 2003, 5, 599-603. Padowitz, D. F.; Messmore, B. W. J. Phys. Chem. B 2000, 104, 9943-9946. Ohshiro, T.; Ito, T.; Buhlmann, P.; Umezawa, Y. Anal. Chem. 2001, 73, 878-883.
73. Phase separation is typically observed in competitive adsorption of two molecules that are significantly different in packing geometry. This phenomenon results from the loss of intermolecular interaction when two different adsorbates are neighboring in a molecular column. By contrast, if the two adsorbates possess very similar packing structures, random mixing occurs. See: Yablon, D. G.; Ertas, D.; Fang, H. B.; Flynn, G. W. Isr. J. Chem. 2003, 43, 383-392. Stevens, F.; Beebe, T. P. Langmuir 1999, 15, 6884-6889. Yablon, D. G.; Wintgens, D.; Flynn, G. W. J. Phys. Chem. B 2002, 106, 5470-5475. Gesquière, A.; De Feyter, S.; De Schryver, F. C.; Schoonbeek, F.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Nano Lett. 2001, 1, 201-206. Cousty, J.; Van, L. P. Phys. Chem. Chem. Phys. 2003, 5, 599-603. Padowitz, D. F.; Messmore, B. W. J. Phys. Chem. B 2000, 104, 9943-9946. Ohshiro, T.; Ito, T.; Buhlmann, P.; Umezawa, Y. Anal. Chem. 2001, 73, 878-883.
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75. The STM images of both 8-9-8 and 8-8-8 dicarbamates generally exhibited low resolution and their column widths are too dose to unambiguously assign the monolayer composition on the basis of the column width alone. Repeated STM experiments on the mixture of the two alkyl dicarbamates in various mole fractions did not provide reliable data on the monolayer composition. Because of the difficulty associated with obtaining conclusive data, competitive monolayer formation between 8-9-8 and 8-8-8 dicarbamates was not further pursued.
76. That there is no significant difference in ΔG of monolayer formation between 8-8-8 and 8-9-8 dicarbamates was not predicted computationally (see Table 2). This may indicate an inadequacy in the computational method employed or signal that comparison with isolated single molecules is not valid in this case. Furthermore, the relative entropic changes are not included in the computation and may not be similar for the two carbamates.
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80. This trend is also found in carboxylic acids. See: Yablon, D. G.; Ertas, D.; Fang, H. B.; Flynn, G. W. Isr. J. Chem. 2003, 43, 383-392.