Contrasting two- and three-dimensional crystal properties of isomeric dialkyl phthalates

Journal of the American Chemical Society

Volumn 129, Issue 49, 2007, Pages 15211-15217

  Plass, Katherine E ^a   Engle, Keary M ^a   Matzger, Adam J ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION; CRYSTAL STRUCTURE; MONOLAYERS; SOLUTIONS; THERMODYNAMIC PROPERTIES;

ADSORPTION STRENGTHS; ISOMERIC DIALKYL PHTHALATES;

ISOMERS;

PHTHALIC ACID ESTER;

ADSORPTION; ARTICLE; BEHAVIOR; CRYSTAL STRUCTURE; ENTHALPY; IONIC STRENGTH; ISOMER; MELTING POINT; MICROSCOPY; MONOLAYER CULTURE; SOLUBILITY; THERMODYNAMICS;

ADSORPTION; CRYSTALLIZATION; GRAPHITE; ISOMERISM; MICROSCOPY, SCANNING TUNNELING; PHTHALIC ACIDS; THERMODYNAMICS;

EID: 37049036591     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0744798     Document Type: Article

References (36)

1. Giancarlo, L. C.; Fang, H. B.; Rubin, S. M.; Bront, A. A.; Flynn, G. W. J. Phys. Chem. B 1998, 102, 10255-10263.
2. Uemura, S.; Samorí, P.; Kunitake, M.; Hirayama, C.; Rabe, J. P. J. Mater. Chem. 2002, 12, 3366-3367.
3. Perronet, K.; Charra, F. Surf. Sci. 2004, 551, 213-218.
4. Kaneda, Y.; Stawasz, M. E.; Sampson, D. L.; Parkinson, B. A. Langmuir 2001, 17, 6185-6195.
5. Kim, K.; Plass, K. E.; Matzger, A. J. J. Am. Chem. Soc. 2005, 127, 4879-4887.
6. Holler, A. C. J. Org. Chem. 1948, 13, 70-74.
7. Brown, R. J. C.; Brown, R. F. C. J. Chem. Educ. 2000, 77, 724-731.
8. Pinal, R. Org. Biomol. Chem. 2004, 2, 2692-2699.
9. Lackinger, M.; Griessl, S.; Markert, T.; Jamitzky, F.; Heckl, W. M. J. Phys. Chem. B 2004, 108, 13652-13655.
10. Gomar-Nadal, E.; Abdel-Mottaleb, M. M. S.; De Feyter, S.; Veciana, J.; Rovira, C.; Amabilino, D. B.; De Schryver, F. C. Chem. Commun. 2003, 906-907.
11. Feng, C. L.; Zhang, Y. J.; Jin, J.; Song, Y. L.; Xie, L. Y.; Qu, G. R.; Jiang, L.; Zhu, D. B. Surf. Sci. 2002, 513, 111-118.
12. Grim, P. C. M.; Vanoppen, P.; Rücker, M.; De Feyter, S.; Valiyaveettil, S.; Moessner, G.; Müllen, K.; De Schryver, F. C. J. Vac. Sci. Technol. B 1997, 15, 1419-1424.
13. Vanoppen, P.; Grim, P. C. M.; Rücker, M.; De Feyter, S.; Moessner, G.; Valiyaveettil, S.; Müllen, K.; De Schryver, F. C. J. Phys. Chem. 1996, 100, 19636-19641.
14. Stevens, F.; Dyer, D. J.; Walba, D. M. Langmuir 1996, 12, 436-440.
15. Meier, C.; Ziener, U.; Landfester, K.; Weihrich, P. J. Phys. Chem. B 2005, 109, 21015-21027.
16. Plass, K. E.; Kim, K.; Matzger, A. J. J. Am. Chem. Soc. 2004, 126, 9042-9053.
17. Plass, K. E.; Engle, K. M.; Cychosz, K. A.; Matzger, A. J. Nano Lett. 2006, 6, 1178-1183.
18. See Plass, K. E.; Grzesiak, A. L.; Matzger, A. J. Acc. Chem. Res. 2007, 40, 287-293 for a discussion of the relationships between molecular and monolayer symmetry in two-dimensional crystals and a comparison between two- and three-dimensional crystal structures.
19. Tao, F.; Bernasek, S. L. Chem. Rev. 2007, 107, 1408-1453.
20. Wei, Y.; Kannappan, K.; Flynn, G. W.; Zimmt, M. B. J. Am. Chem. Soc. 2004, 126, 5318-5322.
21. Schuurmans, N.; Uji-i, H.; Mamdouh, W.; De Schryver, F. C.; Feringa, B. L.; Van Esch, J.; De Feyter, S. J. Am. Chem. Soc. 2004, 126, 13884-13885.
22. The phase observed to form at the surface from multicomponent solutions during the competitive adsorption experiments were not metastable, kinetically favored phases. This was determined by displacement experiments, where a monolayer was formed from pure solution and then rapidly displaced by addition of another isomer.
23. Venkataraman, B.; Breen, J. J.; Flynn, G. W. J. Phys. Chem. 1995, 99, 6608-6619.
24. Yablon, D. G.; Ertas, D.; Fang, H. B.; Flynn, G. W. Isr. J. Chem. 2003, 43, 383-392.
25. Castro, M. A.; Clarke, S. M.; Inaba, A.; Arnold, T.; Thomas, R. K. J. Phys. Chem. B 1998, 102, 10528-10534.
26. Carnelley, T. Philos. Mag. 1882, 13, 112-130.
27. Carnelley, T. Philos. Mag. 1882, 13, 180-193.
28. Gavezzotti, A. J. Chem. Soc., Perkin Trans. 2 1995, 1399-1404.
29. Wei, J. Ind. Eng. Chem. Res. 1999, 38, 5019-5027.
30. Abramowitz, R.; Yalkowsky, S. H. Pharm. Res. 1990, 7, 942-947.
31. Two polymorphs of 17-meta were discovered: form II was obtained from recrystallization from methyl ethyl ketone, and cooling from the melt of form II produced form I. The relative stabilities were determined by allowing saturated solutions of the two polymorphs of 17-meta in phenyloctane to equilibrate. These solutions were filtered, and the precipitates were compared by optical microscopy and powder X-ray diffraction, which indicated that both solids were form I. The same process was monitored in acetone using optical microscopy. The transformation of form II to form I indicates that form I is the more stable polymorph of 17-meta.
32. See ref 5 and (a) 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.
33. (b) Mena-Osteritz, E. Adv. Mater. 2002, 14, 609-616.
34. (c) Mu, Z.-C.; Kong, J.-F.; Wang, Y.; Ye, L.; Yang, G.-D.; Zhang, X. ChemPhysChem 2004, 5, 202-208.
35. (d) Constable, E. C.; Guntherodt, H. J.; Housecroft, C. E.; Merz, L.; Neuburger, M.; Schaffner, S.; Tao, Y. Q. New J. Chem. 2006, 30, 1470-1479 for comparisons of the two- and three-dimensional crystal packing of various compounds.
36. -1).