Two-dimensional crystallization: Self-assembly, pseudopolymorphism, and symmetry-independent molecules

Journal of the American Chemical Society

Volumn 126, Issue 29, 2004, Pages 9042-9053

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

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; COMPUTER SIMULATION; CRYSTALLIZATION; MICROBIOLOGY; MONOLAYERS; SCANNING TUNNELING MICROSCOPY;

INTERMOLECULAR INTERACTIONS; PSEUDOPOLYMORPHS;

SELF ASSEMBLY;

BENZENE DERIVATIVE; ESTER; KETONE; THIOESTER;

ARTICLE; CRYSTALLIZATION; ELECTRICITY; GEOMETRY; MODEL; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR STABILITY; MOLECULE; SCANNING TUNNELING MICROSCOPY;

EID: 3242812132     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0493446     Document Type: Article

References (89)

1. Motherwell, W. D. S.; Ammon, H. L.; Dunitz, J. D.; Dzyabchenko, A.; Erk, P.; Gavezzotti, A.; Hofmann, D. W. M.; Leusen, F. J. J.; Lommerse, J. P. M.; Mooij, W. T. M.; Price, S. L.; Scheraga, H.; Schweizer, B.; Schmidt, M. U.; van Eijck, B. P.; Verwer, P.; Williams, D. E. Acta Crystallogr., Sect. B: Struct. Sci. 2002, 58, 647-661.
2. Lommerse, J. P. M.; Motherwell, W. D. S.; Ammon, H. L.; Dunitz, J. D.; Gavezzotti, A.; Hofmann, D. W. M.; Leusen, F. J. J.; Mooij, W. T. M.; Price, S. L.; Schweizer, B.; Schmidt, M. U.; van Eijck, B. P.; Verwer, P.; Williams, D. E. Acta Crystallogr., Sect. B: Struct. Sci. 2000, 56, 697-714.
3. For recent reviews of the challenges of three-dimensional crystal structure prediction, see: Desiraju, G. R. Nat. Mater. 2002, 1, 77-79.
4. Dunitz, J. D. Chem. Commun. 2003, 545-548.
5. De Feyter, S.; De Schryver, F. C. Chem. Soc. Rev. 2003, 32, 139-150.
6. Giancarlo, L. C.; Flynn, G. W. Acc. Chem. Res. 2000, 33, 491-501.
7. De Feyter, S.; Gesquière, A.; Abdel-Mottaleb, M. M.; Grim, P. C. M.; De Schryver, F. C.; Meiners, C.; Sieffert, M.; Valiyaveettil, S.; Müllen, K. Acc. Chem. Res. 2000, 33, 520-531.
8. Giancarlo, L. C.; Flynn, G. W. Annu. Rev. Phys. Chem. 1998, 49, 297-336.
9. Cyr, D. M.; Venkataraman, B.; Flynn, G. W. Chem. Mater. 1996, 8, 1600-1615.
10. Claypool, C. L.; Faglioni, F.; Goddard, W. A.; Gray, H. B.; Lewis, N. S.; Marcus, R. A. J. Phys. Chem. B 1997, 101, 5978-5995.
11. Faglioni, F.; Claypool, C. L.; Lewis, N. S.; Goddard, W. A. J. Phys. Chem. B 1997, 101, 5996-6020.
12. Kim, K.; Matzger, A. J. J. Am. Chem. Soc. 2002, 124, 8772-8773.
13. Samorí, P.; Severin, N.; Simpson, C. D.; Müllen, K.; Rabe, J. P. J. Am. Chem. Soc. 2002, 124, 9454-9457.
14. Stabel, A.; Heinz, R.; Rabe, J. P.; Wegner, G.; De Schryver, F. C.; Corens, D.; Dehaen, W.; Süling, C. J. Phys. Chem. 1995, 99, 8690-8697.
15. Kim, K.; Plass, K. E.; Matzger, A. J. Langmuir 2003, 19, 7149-7152.
16. Kaneda, Y.; Stawasz, M. E.; Sampson, D. L.; Parkinson, B. A. Langmuir 2001, 17, 6185-6195.
17. Stawasz, M. E.; Parkinson, B. A. Langmuir 2003, 19, 10139-10151.
18. For a thorough treatment of crystal polymorphism, see: Bernstein, J. Polymorphism in Molecular Crystals; Clarendon Press: Oxford, 2002.
19. Steed, J. W. CrystEngComm 2003, 5, 169-179.
20. Several analyses of the frequency of occurrence of Z′ > 1 have been undertaken: (a) Padmaja, N.; Ramakumar, S.; Viswamitra, M. A. Acta Crystallogr., Sect. A 1990, 46, 725-730.
21. (b) Wilson, A. J. C. Acta Crystallogr., Sect. A 1993, 49, 795-806.
22. (c) Brock, C. P.; Dunitz, J. D. Chem. Mater. 1994, 6, 1118-1127.
23. (d) Steiner, T. Acta Crystallogr., Sect. B: Struct. Sci. 2000, 56, 673-676.
24. Correlations between the existence of strong hydrogen bonds in a structure and Z′ & 1 have been suggested: (a) Gavezzotti, A.; Filippini, G. J. Phys. Chem. 1994, 98, 4831-4837.
25. (b) Brock, C. P.; Duncan, L. L. Chem. Mater. 1994, 6, 1307-1312.
26. (c) Brock, C. P. J. Res. Natl. Inst. Stand. Technol. 1996, 101, 321-325.
27. (d) Taylor, R.; Macrae, C. F. Acta Crystallogr., Sect. B: Struct. Sci. 2001, 57, 815-827.
28. (e) Steed, J. W.; Sakellariou, E.; Junk, P. C.; Smith, M. K. Chem.-Eur. J. 2001, 7, 1240-1247.
29. (f) Lehmler, H. J.; Robertson, L. W.; Parkin, S.; Brock, C. P. Acta Crystallogr., Sect. B: Struct. Sci. 2002, 58, 140-147.
30. (g) Brock, C. P. Acta Crystallogr., Sect. B: Struct. Sci. 2002, 58, 1025-1031.
31. (h) Gibson, S. E.; Ibrahim, H.; Steed, J. W. J. Am. Chem. Soc. 2002, 124, 5109-5116.
32. (i) Kuleshova, L. N.; Antipin, M. Y.; Komkov, I. V. J. Mol. Struct. 2003, 647, 41-51.
33. (j) Aitipamula, S.; Desiraju, G. R.; Jaskólski, M.; Nangia, A.; Thaimattam, R. CrystEngComm 2003, 5, 447-450.
34. Buchholz, S.; Rabe, J. P. J. Vac. Sci. Technol., B 1991, 9, 1126-1128.
35. Miura, A.; De Feyter, S.; Abdel-Mottaleb, M. M. S.; Gesquière, A.; Grim, P. C. M.; Moessner, G.; Sieffert, M.; Klapper, M.; Müllen, K.; De Schryver, F. C. Langmuir 2003, 19, 6474-6482.
36. Hoeppener, S.; Chi, L.; Fuchs, H. ChemPhysChem 2003, 4, 494-498.
37. De Feyter, S.; Gesquière, A.; Klapper, M.; Müllen, K.; De Schryver, F. C. Nano Lett. 2003, 3, 1485-1488.
38. Olson, J. A.; Bühlmann, P. Anal. Chem. 2003, 75, 1089-1093.
39. Wintgens, D.; Yablon, D. G.; Flynn, G. W. J. Phys. Chem. B 2003, 107, 173-179.
40. Cai, Y.; Bernasek, S. L. J. Am. Chem. Soc. 2003, 125, 1655-1659.
41. De Feyter, S.; Larsson, M.; Schuurrnans, N.; Verkuijl, B.; Zoriniants, G.; Gesquière, A.; Abdel-Mottaleb, M. M.; van Esch, J.; Feringa, B. L.; van Stam, J.; De Schryver, F. Chem.-Eur. J. 2003, 9, 1198-1206.
42. De Feyter, S.; Larsson, M.; Gesquière, A.; Verheyen, H.; Louwet, F.; Groenendaal, B.; van Esch, J.; Feringa, B. L.; De Schryver, F. ChemPhysChem 2002, 3, 966-969.
43. 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.
44. Gesquière, A.; Abdel-Mottaleb, M. M. S.; De Feyter, S.; De Schryver, F. C.; Schoonbeek, F.; van Esch, J.; Kellogg, R. M.; Feringa, B. L.; Calderone, A.; Lazzaroni, R.; Brédas, J. L. Langmuir 2000, 16, 10385-10391.
45. De Feyter, S.; Grim, P. C. M.; van Esch, J.; Kellogg, R. M.; Feringa, B. L.; De Schryver, F. C. J. Phys. Chem. B 1998, 102, 8981-8987.
46. Matzger, A. J.; Kim, K. Polym. Mater. Sci. Eng. 2003, 89, 825-826.
47. De Feyter, S.; Gesquière, A.; Wurst, K.; Amabilino, D. B.; Veciana, J.; De Schryver, F. C. Angew. Chem., Int. Ed. 2001, 40, 3217-3220.
48. Azumi, R.; Götz, G.; Debaerdemaeker, T.; Bäuerle, P. Chem.-Eur. J. 2000, 6, 735-744.
49. Eichhorst-Gerner, K.; Stabel, A.; Moessner, G.; Declerq, D.; Valiyaveettil, S.; Enkelmann, V.; Müllen, K.; Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1492-1495.
50. Yeo, Y. H.; McGonigal, G. C.; Thomson, D. J. Langmuir 1993, 9, 649-651.
51. Bowden, F. P.; Tabor, D. The Friction and Lubrication of Solids; Clarendon Press: Oxford, 1954.
52. Samorí, P.; Rabe, J. P. J. Phys.: Condens. Matter 2002, 14, 9955-9973.
53. Hoeppener, S.; Wonnemann, J.; Chi, L.; Erker, G.; Fuchs, H. ChemPhysChem 2003, 4, 490-494.
54. Abdel-Mottaleb, M. M. S.; Schuurmans, N.; De Feyter, S.; Van Esch, J.; Feringa, B. L.; De Schryver, F. C. Chem. Commun. 2002, 1894-1895.
55. Lang, M.; Grzesiak, A. L.; Matzger, A. J. J. Am. Chem. Soc. 2002, 124, 14834-14835.
56. Mitchell, C. A.; Yu, L.; Ward, M. D. J. Am. Chem. Soc. 2001, 123, 10830-10839.
57. Last, J. A.; Hillier, A. C.; Hooks, D. E.; Maxson, J. B.; Ward, M. D. Chem. Mater. 1998, 10, 422-437.
58. Hahn, T., Ed. International Tables for Crystallography: Volume A Space-Group Symmetry, 5th ed.; Kluwer Academic Publishers: Boston, 2002.
59. Rabe, J. P.; Buchholz, S. Phys. Rev. Lett. 1991, 66, 2096-2099.
60. Rabe, J. P.; Buchholz, S. Science 1991, 253, 424-427.
61. Eng, L. M.; Fuchs, H.; Buchholz, S.; Rabe, J. P. Ultramicroscopy 1992, 42-44, 1059-1066.
62. Lee, H. S.; Iyengar, S.; Musselman, I. H. Langmuir 1998, 14, 7475-7483.
63. Lee, H. S.; Iyengar, S.; Musselman, I. H. Anal. Chem. 2001, 73, 5532-5538.
64. Kitaigorodskii, A. I. Acta Crystallogr. 1965, 18, 585-590.
65. Kitaigorodskii, A. I. Organic Chemical Crystallography; Consultants Bureau: New York, 1959.
66. Burger, A.; Ramberger, R. Mikrochim. Acta 1979, 2, 259-271.
67. Burger, A.; Ramberger, R. Mikrochim. Acta 1979, 2, 273-316.
68. The 1,3-diester-substituted benzenes are described as "odd esters" or "even esters" on the basis of the parity of the number of carbons in each alkyl chain.
69. 2).
70. Although numerous definitions have been offered for the term pseudopolymorphism, as reviewed by Bernstein, we use the definition from Nangia, A.; Desiraju, G. R. Chem. Commun. 1999, 605-606 that refers to "crystalline forms that differ in the nature or stoichiometry of included solvent molecules". Applying this definition to two-dimensions implies that monolayers of a given compound that differ in stoichiometry with the surface are pseudopolymorphs.
71. Stabel, A.; Heinz, R.; De Schryver, F. C.; Rabe, J. P. J. Phys. Chem. 1995, 99, 505-507.
72. In this context, it is interesting to note that a smooth interface surrounding a thermodynamically unstable domain prolongs its existence.
73. Baker, R. T.; Mougous, J. D.; Brackley, A.; Patrick, D. L. Langmuir 1999, 15, 4884-4891.
74. For typical C-H⋯O bond geometries as well as a review of these types of weak hydrogen bonds, see: Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond In Structural Chemistry and Biology; Oxford University Press: Oxford, 1999.
75. A similar difference in the strength of hydrogen bonds to amines from ketone and ester donors has been observed: Ziao, N.; Laurence, C.; Le Questel, J. Y. CrystEngComm 2002, 4, 326-335.
76. The difficulty in controlling and reproducing the formation of some metastable polymorphs is a widely recognized phenomenon in the field of three-dimensional crystallization: Dunitz, J. D.; Bernstein, J. Acc. Chem. Res. 1995, 28, 193-200.
77. It might have been expected that the requirement of adsorption to the surface would add to frustration of close packing, making Z′ > 1 more common in two-dimensional crystals. Surface reconstructions involving ionic or covalent crystals often display extremely large numbers of inequivalent sites. However, experiments carried out on physisorbed monolayers reveal that the additional restriction of two-dimensionality due to the surface does not add substantially to the appearance of Z′ > 1, as is apparent from the comparison of the statistics of two- and three-dimensional crystals. This may be observed because of the relatively weak and nondirectional interactions involved with these physisorbed monolayers.
78. McGonigal, G. C.; Bernhardt, R. H.; Yeo, Y. H.; Thomson, D. J. J. Vac. Sci. Technol., B 1991, 9, 1107-1110.
79. A few examples of Z′ > 1 in two-dimensional crystals have been observed by other preparation methods. An example of Z′ = 2 can be found in vapor-formed two-dimensional crystals of nickel(II) octaethylporphyrin: Scudiero, L.; Barlow, D. E.; Hipps, K. W. J. Phys. Chem. B 2002, 106, 996-1003.
80. An example of Z′ > 2 can be found in solvent-evaporated two-dimensional crystals of alkyl-substituted triphenylenes: Wu, P.; Zeng, Q. D.; Xu, S. D.; Wang, C.; Yin, S. X.; Bai, C. L. ChemPhysChem 2001, 2, 750-754. Monolayers formed by these techniques have fewer opportunities to reorganize as compared to monolayers remaining in solution for extended periods, and thus may be kinetically favored phases, while monolayers imaged at the solution-solid interface are more likely to be the thermodynamically favored structure.
81. Liquid crystals of alkylcyanobiphenyls form multiple asymmetric molecules on graphite that can be observed by STM. However, the observed layer is not a two-dimensional crystal because it is part of a structure with three-dimensional order. Frommer, J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1298-1328.
82. Cyr, D. M.; Venkataraman, B.; Flynn, G. W.; Black, A.; Whitesides, G. M. J. Phys. Chem. 1996, 100, 13747-13759.
83. Venkataraman, B.; Flynn, G. W.; Wilbur, J. L.; Folkers, J. P.; Whitesides, G. M. J. Phys. Chem. 1995, 99, 8684-8689.
84. Among highly polymorphic organic compounds that have been structurally characterized, carbamazepine is the only one where the change between the four polymorphs is related primarily to weak hydrogen bonding. Grzesiak, A. L.; Lang, M.; Kim, K.; Matzger, A. J. J. Pharm. Sci. 2003, 92, 2260-2271.
85. Bernstein, J.; Davey, R. J.; Henck, J. O. Angew. Chem., Int. Ed. 1999, 38, 3441-3461.
86. For a novel mechanism of concomitant polymorphism in three-dimensions, see: Yu, L. J. Am. Chem. Soc. 2003, 125, 6380-6381.
87. Bonafede, S. J.; Ward, M. D. J. Am. Chem. Soc. 1995, 117, 7853-7861.
88. Carter, P. W.; Ward, M. D. J. Am. Chem. Soc. 1993, 115, 11521-11535.
89. Sun, H. J. Phys. Chem. B 1998, 102, 7338-7364.