A chiral self-assembled monolayer derived from a resolving agent and its performance as a crystallization template for an organic compound from organic solvents

Chemistry - A European Journal

Volumn 18, Issue 50, 2012, Pages 15984-15993

  Bejarano Villafuerte, Ángela ^a   Van Der Meijden, Maarten W ^b   Lingenfelder, Magalí ^a   Wurst, Klaus ^c   Kellogg, Richard M ^b   Amabilino, David B ^a  

^a INSTITUT DE CIÈNCIA DE MATERIALS DE BARCELONA ICMAB CSIC   (Spain)

^b Syncom BV   (Netherlands)

^c UNIVERSITY OF INNSBRUCK   (Austria)

Author keywords

chirality; crystal growth; monolayers; self assembly

Indexed keywords

ABSOLUTE CONFIGURATION; CRYSTAL FORMS; CRYSTALLIZATION TEMPLATES; EVAPORATION RATE; HETEROGENEOUS NUCLEATION; HOMOGENEOUS SAMPLES; ISOPROPANOL SOLUTION; METALLIC GOLD; MONOCRYSTALLINE; NONAQUEOUS SOLUTIONS; NUCLEATION AND GROWTH; NUCLEATION SITES; ORGANIC CRYSTAL; ORGANIC MOLECULES; ORGANIC SOLUTIONS; PHOSPHATE GROUP; POLYCRYSTALLINE; POLYCRYSTALLINE GOLD; RESOLVING AGENTS; SYNTHETIC INTERMEDIATES; TEMPLATE LAYERS; THIOL COMPOUNDS; X RAY STRUCTURAL ANALYSIS;

CHIRALITY; CRYSTAL GROWTH; CRYSTAL STRUCTURE; ENANTIOMERS; EVAPORATION; GOLD; MONOLAYERS; NUCLEATION; ORGANIC POLYMERS; ORGANIC SOLVENTS; SCANNING ELECTRON MICROSCOPY; SELF ASSEMBLED MONOLAYERS; SELF ASSEMBLY; SURFACE ROUGHNESS; TWO DIMENSIONAL;

STEREOCHEMISTRY;

EID: 84870594224     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201202681     Document Type: Article

References (82)

1. I. Weissbuch, I. Kuzmenko, M. Berfeld, L. Leiserowitz, M. Lahav, J. Phys. Org. Chem. 2000, 13, 426-434.
2. K. H. Ernst, Top. Curr. Chem. 2006, 265, 209-252
3. R. Raval, Chem. Soc. Rev. 2009, 38, 707-721
4. J. A. A. W. Elemans, I. De Cat, H. Xu, S. De Feyter, Chem. Soc. Rev. 2009, 38, 722-736.
5. F. Masini, N. Kalashnyk, M. M. Knudsen, J. R. Cramer, E. Lægsgaard, F. Besenbacher, K. V. Gothelf, T. R. Linderoth, J. Am. Chem. Soc. 2011, 133, 13910-13913
6. K. Tahara, H. Yamaga, E. Ghijsens, K. Inukai, J. Adisoejoso, M. O. Blunt, S. De Feyter, Y. Tobe, Nat. Chem. 2011, 3, 714-719.
7. A. P. H. J. Schenning, P. Jonkheijm, E. Peeters, E. W. Meijer, J. Am. Chem. Soc. 2001, 123, 409-416
8. R. Fasel, M. Parschau, K. H. Ernst, Angew. Chem. 2003, 115, 5336-5339
9. Angew. Chem. Int. Ed. 2003, 42, 5178-5181
10. M. C. Blüm, E. Cavar, M. Pivetta, F. Patthey, W. D. Schneider, Angew. Chem. 2005, 117, 5468-5471
11. Angew. Chem. Int. Ed. 2005, 44, 5334-5337
12. P. Yuan, L. Z. Zhao, N. A. Liu, G. F. Wei, Y. H. Wang, G. J. Auchterlonie, J. Drennan, G. Q. Lu, J. Zou, C. Z. Yu, Chem. Eur. J. 2010, 16, 1629-1637
13. E. V. Iski, H. L. Tierney, A. D. Jewell, E. C. H. Sykes, Chem. Eur. J. 2011, 17, 7205-7212
14. S. Azeroual, J. Surprenant, T. D. Lazzara, M. Kocun, Y. Tao, L. A. Cuccia, J.-M. Lehn, Chem. Commun. 2012, 48, 2292-2294
15. C. Viedma, J. E. Ortiz, T. de Torres, P. Cintas, Chem. Commun. 2012, 48, 3623-3625
16. T. Shiraki, A. Dawn, Y. Tsuchiya, T. Yamamoto, S. Shinkai, Chem. Commun. 2012, 48, 7091-7093.
17. V. I. Kopp, Z. Q. Zhang, A. Z. Genack, Prog. Quantum Electron. 2003, 27, 369-416
18. A. Ghosh, P. Fischer, Phys. Rev. Lett. 2006, 97, 173002
19. V. Rodriguez, G. Koeckelberghs, T. Verbiest, Chem. Phys. Lett. 2007, 450, 76-79
20. M. Siltanen, E. Vuorimaa, H. Lemmetyinen, P. Ihalainen, J. Peltonen, M. Kauranen, J. Phys. Chem. B 2008, 112, 1940-1945
21. S. Debnath, J.-F. Bergamini, F. Artzner, C. Mériadec, F. Camerel, M. Fourmigué, Chem. Commun. 2012, 48, 2283-2285
22. A. Yamazaki, T. Akitsu, RSC Advances 2012, 2, 2975-2980
23. A. Ryabchun, A. Bobrovsky, A. Sobolewska, V. Shibaev, J. Stumpe, J. Mater. Chem. 2012, 22, 6245-6250.
24. K. Ariga, G. J. Richards, S. Ishihara, H. Izawa, J. P. Hill, Sensors 2010, 10, 6796-6820
25. T. Sun, G. Qing, B. Su, L. Jiang, Chem. Soc. Rev. 2011, 40, 2909-2921
26. M. Zhang, G. Qing, T. Sun, Chem. Soc. Rev. 2012, 41, 1972-1984.
27. A. Sarfraz, A. Simo, R. Fenger, W. Christen, K. Rademann, U. Panne, F. Emmerling, Cryst. Growth Des. 2012, 12, 583-588.
28. A. Y. Lee, I. S. Lee, A. S. Myerson, Chem. Eng. Technol. 2006, 29, 281-285
29. A. Singh, I. S. Lee, A. S. Myerson, Cryst. Growth Des. 2009, 9, 1182-1185
30. A. Singh, I. S. Lee, K. Kim, A. S. Myerson, CrystEngComm 2011, 13, 24-32
31. K. Kim, A. Centrone, T. A. Hatton, A. S. Myerson, CrystEngComm 2011, 13, 1127-1131.
32. P. C. Rieke, B. J. Tarasevich, L. L. Wood, M. H. Engelhard, D. R. Baer, G. E. Fryxell, C. M. John, D. A. Laken, M. C. Jaehnig, Langmuir 1994, 10, 619-622
33. J. Aizenberg, A. J. Black, G. H. Whitesides, J. Am. Chem. Soc. 1999, 121, 4500-4509
34. R. Hiremath, S. W. Varney, J. A. Swift, Chem. Mater. 2004, 16, 4948-4954
35. D. Zacher, A. Baunemann, S. Hermes, R. A. Fischer, J. Mater. Chem. 2007, 17, 2785-2792
36. B. Pokroy, V. F. Chernow, J. Aizenberg, Langmuir 2009, 25, 14002-14006.
37. L. Pasteur, C. R. Acad. Sci. 1853, 37, 162-166
38. L. Pasteur, Ann. Chim. (Paris) 1853, 38, 437-483
39. J. Jacques, A. Collet, S. H. Wilen, Enantiomers, Racemates, and Resolutions, Krieger Publishing, Malabar, 1994
40. CRC Handbook of Optical Resolutions via Diastereomeric Salt Formation (Ed.:, D. Kozma,), CRC Press, New York, 2002
41. E. Fogassy, M. Nógrádi, D. Kozma, G. Egri, E. Pálovics, V. Kiss, Org. Biomol. Chem. 2006, 4, 3011-3030
42. G. Coquerel, G. D. B. Amabilino, in Chirality at the Nanoscale (Ed.:, D. B. Amabilino,), Wiley-VCH, Weinheim, 2009, pp. 305-348.
43. R. Sancho, C. Minguillon, Chem. Soc. Rev. 2009, 38, 797-805.
44. Y. Mastai, Chem. Soc. Rev. 2009, 38, 772-780.
45. D. H. Dressler, Y. Mastai, Chirality 2007, 19, 358-365.
46. D. H. Dressler, I. Hod, Y. Mastai, J. Cryst. Growth 2008, 310, 1718-1724.
47. M. Ejgenberg, Y. Mastai, Chem. Commun. 2011, 47, 12161-12163.
48. Y. Diao, A. S. Myerson, T. A. Hatton, B. L. Trout, Langmuir 2011, 27, 5324-5334.
49. M. Leeman, F. Querniard, T. R. Vries, B. Kaptein, R. M. Kellogg, Org. Process Res. Dev. 2009, 13, 1379-1381.
50. T. Vries, H. Wynberg, E. van Echten, J. Koek, W. ten Hoeve, R. M. Kellogg, Q. B. Broxterman, A. Minnaard, B. Kaptein, S. van der Sluis, L. Hulshof, J. Kooistra, Angew. Chem. 1998, 110, 2491-2496
51. Angew. Chem. Int. Ed. 1998, 37, 2349-2354
52. J. W. Nieuwenhuijzen, R. F. P. Grimbergen, C. Koopman, R. M. Kellogg, T. R. Vries, K. Pouwer, E. van Echten, B. Kaptein, L. A. Hulshof, Q. B. Broxterman, Angew. Chem. 2002, 114, 4457-4462
53. Angew. Chem. Int. Ed. 2002, 41, 4281-4286
54. J. Dalmolen, T. D. Tiemersma-Wegman, J. W. Nieuwenhuijzen, M. van der Sluis, E. van Echten, T. R. Vries, B. Kaptein, Q. B. Broxterman, R. M. Kellogg, Chem. Eur. J. 2005, 11, 5619-5624.
55. J. C. Love, L. A. Estroff, J. K. Kriebel, R. G. Nuzzo, G. M. Whitesides, Chem. Rev. 2005, 105, 1103-1170
56. P. S. Weiss, Acc. Chem. Res. 2008, 41, 1772-1781
57. E. Prats-Alfonso, F. Albericio, J. Mater. Chem. 2011, 21, 7643-7648.
58. W. ten Hoeve, H. Wynberg, J. Org. Chem. 1985, 50, 4508-4514.
59. L. Pérez-García, D. B. Amabilino, Chem. Soc. Rev. 2002, 31, 342-356
60. L. Pérez-García, D. B. Amabilino, Chem. Soc. Rev. 2007, 36, 941-967.
61. M. S. Leeman, Resolution of Racemates by Crystallization, Thesis, R. U. Groningen, 2009.
62. D. Kikuchi, S. Sakaguchi, Y. Ishii, J. Org. Chem. 1998, 63, 6023-6026.
63. B. Fabisch, T. N. Mitchell, J. Organomet. Chem. 1984, 269, 219-221.
64. N. Bumagin, E. V. Luzikova, J. Organomet. Chem. 1997, 532, 271-273.
65. C.-C. Han, R. Balakumar, Tetrahedron Lett. 2006, 47, 8255-8258.
66. G. E. Poirier, Langmuir 1997, 13, 2019-2026
67. R. Yamada, K. Uosaki, Langmuir 1998, 14, 855-861
68. E. Torres, A. T. Blumenau, P. U. Biedermann, Phys. Rev. B 2009, 79, 075440.
69. C. Vericat, M. E. Vela, R. C. Salvarezza, Phys. Chem. Chem. Phys. 2005, 7, 3258-3268.
70. K. Hinds, D. W. Grainger, Langmuir 1996, 12, 5083-5086.
71. R. M. Petoral Jr., F. Björefors, K. Uvdal, J. Phys. Chem. B 2006, 110, 23410-23410.
72. A. Al-Mahboob, J. T. Sadowsk, T. Nishihara, Y. Fujikawa, Q. K. Xu, K. Nakajima, T. Sakurai, Surf. Sci. 2007, 601, 1311-1318
73. P. De Marco, F. Fioriti, F. Bisti, P. Parisse, S. Santucci, L. Ottaviano, J. Appl. Phys. 2011, 109, 063508.
74. M. Zolk, F. Eisert, J. Pipper, S. Herrwerth, W. Eck, M. Buck, M. Grunze, Langmuir 2000, 16, 5849-5852
75. N. N. Gosvami, S. K. Sinha, M. P. Srinivasan, S. J. O'Shea, J. Phys. Chem. C 2008, 112, 297-302
76. A. R. Siler, R. A. Walker, J. Phys. Chem. C 2011, 115, 9637-9643
77. C.-H. Shen, J.-C. Lin, Langmuir 2011, 27, 7091-7098
78. C.-H. Shen, J.-C. Lin, Langmuir 2012, 28, 640-647.
79. J. R. Cox, M. Dabros, J. A. Shaffer, V. R. Thalladi, Angew. Chem. 2007, 119, 2034-2037
80. Angew. Chem. Int. Ed. 2007, 46, 1988-1991.
81. S. Wei, M. Mauksch, S. B. Tsogoeva, Chem. Eur. J. 2009, 15, 10255-10262
82. D. B. Amabilino, R. M. Kellogg, Isr. J. Chem. 2011, 51, 1034-1040.