Self-assembly of tetrathiafulvalene derivatives at a liquid/solid interface - Compositional and constitutional influence on supramolecular ordering

Journal of Materials Chemistry

Volumn 15, Issue 43, 2005, Pages 4601-4615

  Abdel Mottaleb, Mohamed M S ^a,d   Gomar Nadal, Elba ^b,e   Surin, Mathieu ^c   Uji i, Hiroshi ^a   Mamdouh, Wael ^a   Veciana, Jaume ^b   Lemaur, Vincent ^c   Rovira, Concepcio ^b   Cornil, Jérôme ^c   Lazzaroni, Roberto ^c   Amabilino, David B ^b   De Feyter, Steven ^a   De Schryver, Frans C ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

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

^c UNIVERSITY OF MONS   (Belgium)

^d CHEMNITZ UNIVERSITY OF TECHNOLOGY   (Germany)

^e UNIVERSITY OF MARYLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; GRAPHITE; MOLECULES; SCANNING TUNNELING MICROSCOPY; SOLUTIONS; SOLVENTS;

MOLECULAR MODELLING; NON-VOLATILE ORGANIC SOLUTIONS;

SELF ASSEMBLY;

EID: 27944461072     PISSN: 09599428     EISSN: 13645501     Source Type: Journal    
DOI: 10.1039/b509336h     Document Type: Article

References (137)

1. (a) J. S. Lindsey, New J. Chem., 1991, 15, 153-180;
2. (b) D. Philp and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 1996, 35, 1155-1196;
3. (c) D. S. Lawrence, T. Jiang and M. Levett, Chem. Rev., 1995, 95, 2229-2260;
4. (d) A. Ulman, Chem. Rev., 1996, 96, 1533-1554;
5. (e) L. M. Greig and D. Philp, Chem. Soc. Rev., 2001, 30, 287-302;
6. (f) O. Ikkala and G. ten Blinke, Chem. Commun., 2004, 2131-2137;
7. (g) S. De Feyter and F. C. De Schryver, J. Phys. Chem. B, 2005, 109, 4290-4302;
8. (h) H. M. Keizer and R. P. Sijbesma, Chem. Soc. Rev., 2005, 34, 226-234 and references therein.
9. (a) Nanotechnology, ed. G. Timp, Springer-Verlag, New York, 1999. For recent articles, see:
10. (b) A. Nojeh, G. W. Lakatos, S. Peng, K. Cho and R. F. W. Pease, Nano Lett., 2003, 3, 1187-1190;
11. (c) L. Fu, L. C. Cao, Y. Q. Liu and D. B. Zhu, Adv. Colloid Interface Sci., 2004, 111, 133-157;
12. (d) P. M. Mendes, A. H. Flood and J. F. Stoddart, Appl. Phys. A, 2005, 80, 1197-1209;
13. (e) J. Y. Ouyang, C. W. Chu, D. Sieves and Y. Yang, Appl. Phys. Lett., 2005, 86, 123507;
14. (f) A. Vaseashta and J. Irudayaraj, J. Optoelectron. Adv. Mater., 2005, 7, 35-42;
15. (g) A. A. Kornyshev, A. M. Kumetsov and J. Ulstrup, ChemPhysChem, 2005, 6, 583-586;
16. (h) A. P. H. J. Scheming and E. W. Meijer, Chem. Commun., 2005, 3245-3258.
17. (a) P. Packan, Science, 1999, 285, 2079-2081;
18. (b) C. Joachim, J. K. Gimzewski and A. Aviram, Nature, 2000, 408, 541-548.
19. (a) G. A. Ozin, Adv. Mater., 1992, 2, 612-649;
20. (b) R. D. Piner, J. Zhu, F. Xy, S. Hong and C. A. Mirkin, Science, 1999, 283, 661-663;
21. (c) S. Hong, J. Zhu and C. A. Mirkin, Science, 1999, 286, 523-525;
22. (d) R. Dagani, Chem. Eng. News, 2000, 16, 25-32.
23. (a) C. P. Collier, G. Mattersteig, E. W. Wong, Y. Luo, K. Beverly, J. Sampaio, F. Raymo, J. F. Stoddart and J. R. Heath, Science, 2000, 289, 1172-1175;
24. (b) A. R. Pease, J. O. Jeppesen, J. F. Stoddart, Y. Luo, C. P. Collier and J. R. Heath, Acc. Chem. Res., 2001, 34, 433-444;
25. (c) J. Chen, M. A. Reed, D. W. Price and J. M. Tour, Appl. Phys. Lett., 2001, 78, 3735-3737;
26. (d) J. Chen, M. A. Reed, A. M. Rawlett and J. M. Tour, Science, 1999, 286, 1550-1552;
27. (e) R. L. Carroll and C. B. Gorman, Angew. Chem., Int. Ed., 2002, 41, 4378-4400;
28. (f) R. M. Metzger, Chem. Rev., 2003, 103, 3803-3834;
29. (g) P. Samori and J. P. Rabe, J. Phys.: Condens. Matter, 2002, 14, 9955-9973;
30. (h) G. Maruccio, R. Cingolani and R. Rinaldi, J. Mater. Chem., 2004, 14, 542-554.
31. (a) G. E. Poirier, Chem. Rev., 1997, 97, 1117-1127;
32. (b) A. Ulman, Acc. Chem. Res., 2001, 34, 855-863 and references therein;
33. (c) H. I. Kim, Acc. Chem. Res., 2002, 35, 547-553;
34. (d) C. G. Zeng, B. Li, B. Wang, H. Q. Wang, K. D. Wang, Y. L. Yang, J. G. Hou and Q. S. Zhu, J. Chem. Phys., 2002, 117, 851-856.
35. (a) A. Ulman, An Introduction to Ultrathin Organic Films, Academic Press: San Diego, 1991;
36. (b) F. Schreiber, Prog. Surf. Sci., 2000, 65, 151-256.
37. (a) J. Zhao and K. Uosaki, Nano Lett., 2002, 2, 137-140;
38. (b) C. B. Gorman, R. L. Carroll and R. Fuierer, Langmuir, 2001, 17, 6923-6930.
39. (a) J. P. Rabe and S. Buchholz, Science, 1991, 253, 424-427;
40. (b) L. C. Giancarlo and G. W. Flynn, Annu. Rev. Phys. Chem., 1998, 49, 297-336;
41. (c) S. De Feyter, A. Gesquière, M. M. S. Abdel-Mottaleb, P. C. Grim, C. Meiners, M. Sieffert, S. Valiyaveettil, K. Müllen and F. C. De Schryver, Acc. Chem. Res., 2000, 33, 520-531;
42. (d) P. Samori, J. Mater. Chem., 2004, 14, 1353-1366.
43. (a) A. Gesquière, M. M. Abdel-Mottaleb, S. De Feyter, F. C. De Schryver, M. Sieffert, K. Müllen, A. Calderone, R. Lazzaroni and J.-L. Brédas, Chem. Eur. J., 2000, 6, 20, 3739-3746;
44. (b) T. R. Baker, J. D. Mougous, A. Brackley and D. L. Patrick, Langmuir, 1999, 15, 4884-4891;
45. (c) F. Stevens and T. P. Beebe, Langmuir, 1999, 15, 6884-6889;
46. (d) J. V. Barth, T. Zambelli, J. Wintterlin, R. Schuster and G. Ertl, Phys. Rev. B: Condens. Matter, 1997, 55, 12902-12905;
47. (e) J. K. Gimzewski, C. Joachim, R. R. Schlittier, V. Langlais, H. Tang and I. Johannsen, Science, 1998, 281, 531-533;
48. (f) J. P. Rabe and S. Buchholz, Phys. Rev. Lett., 1991, 66, 2096-2099;
49. (g) A. Stabel, R. Heinz, F. C. De Schryver and J. P. Rabe, J. Phys. Chem., 1995, 99, 505-507.
50. (a) M. M. S. Abdel-Mottaleb, N. Schuurmans, S. De Feyter, J. Van Esch, B. L. Feringa and F. C. De Schryver, Chem. Commun., 2002, 1894-1895;
51. (b) S. Hoeppener, J. Wonnemann, L. Chi, G. Erker and H. Fuchs, ChemPhysChem, 2003, 4, 490-494;
52. (c) S. Hoeppener, L. Chi and H. Fuchs, ChemPhysChem, 2003, 4, 494-498.
53. (a) S. De Feyter and F. C. De Schryver, Chem. Soc. Rev., 2003, 32, 139-150;
54. (b) S. De Feyter, M. Larsson, N. Schuurmans, B. Verkuijl, G. Zoriniants, A. Gesquière, M. M. Abdel-Mottaleb, J. van Esch, B. L. Feringa, J. van Stam and F. C. De Schryver, Chem. Eur. J., 2003, 9, 5, 1198-1205;
55. (c) J. A. Theobald, N. S. Oxtoby, M. A. Philips, N. R. Champness and P. H. Beton, Nature, 2003, 424, 1029-1031;
56. (d) C. L. Claypool, F. Faglioni, W. A. Goddard, III and N. S. Lewis, J. Phys. Chem. B, 1999, 103, 7077-7080;
57. (e) X. Qiu, C. Wang, W. Zeng, B. Xu, S. Yin, H. Wang, S. Xu and C. Bai, J. Am. Chem. Soc., 2000, 122, 5550-5556;
58. (f) X. Qiu, C. Wang, S. Yin, Q. Zeng, B. Xu and C. Bai, J. Phys. Chem. B, 2000, 104, 3570-3574;
59. (g) E. Mena-Osteritz and P. Bauerle, Adv. Mater., 2001, 14, 243-246;
60. (h) A. Dmitriev, H. Spilmann, N. Lin, J. V. Barth and K. Kern, Angew. Chem., Int. Ed., 2003, 42, 2670-2673;
61. (f) P. Samori, N. Severin, C. D. Simpson, K. Müllen and J. P. Rabe, J. Am. Chem. Soc., 2002, 124, 9454-9457.
62. (a) C. Messerschmidt, A. Schulz, J. P. Rabe, A. Simon, O. Marti and J.-H. Fuhrhop, Langmuir, 2000, 16, 1299-1305;
63. (b) X. Du and V. Hlady, J. Phys. Chem. B, 2002, 106, 7295-7299;
64. (c) J. Yin, Q. Guo, R. E. Palmer, N. Campos and J. K. M. Sanders, J. Phys. Chem. B, 2003, 107, 209-216;
65. (d) J. J. Garcia-Lopez, S. Zapotoczny, P. Timmermen, F. C. J. M. van Veggel, J. Vancso, M. Crego-Calama and D. N. Reinhoudt, Chem. Commun., 2003, 352-353.
66. (a) M. E. Stawasz, D. L. Sampson and B. A. Parkinson, Langmuir, 2000, 16, 2326;
67. (b) Y. Kaneda, M. E. Stawasz, D. L. Sampson and B. A. Parkinson, Langmuir, 2001, 17, 6185-6195;
68. (c) P. Wu, Q. D. Zeng, S. D. Xu, C. Wang, S. X. Yin and C. L. Bai, ChemPhysChem, 2001, 2, 750-754.
69. (a) M. B. Nielsen, C. Lomholt and J. Becher, Chem. Soc. Rev., 2000, 29, 153-164;
70. (b) J. L. Segura and N. Martín, Angew. Chem., Int. Ed., 2001, 40, 1372-1409.
71. (a) M. R. J. Bryce, Chem. Soc. Rev., 1991, 20, 355-390;
72. (b) N. S. Nalwa, Handbook of Organic Conductive Molecules and Polymers, vol. I, John Wiley & Sons, New York, 1997.
73. M. Mas-Torrent, P. Hadley, S. T. Bromley, X. Ribas, J. Tarres, M. Mas, E. Molins, J. Veciana and C. Rovira, J. Am. Chem. Soc., 2004, 126, 8546-8553.
74. (a) T. Sleator and T. Tycko, Phys. Rev. Lett., 1998, 60, 1418-1421;
75. (b) S. N. Magonov and M.-H. Whangbo, Adv. Mater., 1994, 6, 355-371;
76. (c) N. A. Kato, M. Hara, H. Sasabe and W. Knoll, Nanotechnology, 1996, 7, 122-127;
77. (d) S. N. Maganov, G. Bar, E. Seller, E. B. Yagubskii, E.E. Laukhina and H.-J. Cantow, Ultramicroscopy, 1992, 42-44, 1009;
78. (e) N. Ara-Kato, K. Yase, H. Shigekawa, M. Yoshimura and A. Kawazu, Synth. Met., 1995, 70, 1245-1246;
79. (f) J. A. Last, A. C. Hillier, D. E. Hooks, J. B. Masón and M. D. Ward, Chem. Mater., 1998, 10, 422-437;
80. (g) Z. Z. Wang, J. C. Girard, C. Pasquier, D. Jérome and K. Bechgaard, Phys. Rev. B: Condens. Matter, 2003, 67, 121401(R).
81. E. Gomar-Nadal, M. M. S. Abdel-Mottaleb, S. De Feyter, J. Veciana, C. Rovira, D. B. Amabilino and F. C. De Schryver, Chem. Commun., 2003, 906-907.
82. M. M. S. Abdel-Mottaleb, E. Gomar-Nadal, S. De Feyter, M. Zdanowska, J. Veciana, C. Rovira, D. B. Amabilino and F. C. De Schryver, Nano Lett., 2003, 3, 1375-1378.
83. J. J. Novoa, M. C. Rovira, C. Rovira, J. Veciana and J. Tarrés, Adv. Mater., 1995, 7, 233.
84. (a) S. A. Shikin, T. S. Berzina, P. S. Sotnikov, V. I. Troitsky, O. Y. Nielands, G. G. Pukitis and V. Y. Khodorkovsky, Biol. Membr., 1990, 7, 1111-1117;
85. (b) T. S. Berzina, V. I. Troitsky and L. G. Yanusova, Biol. Membr., 1990, 7, 1165-1172;
86. (c) K. Naito, A. Miura and M. Azuma, J. Am. Chem. Soc., 1991, 113, 6386-6395;
87. (d) A. S. Dhindsa, Y.-P. Song, J. P. Badyal, M. R. Bryce, Y. M. Lvov, M. C. Petty and J. Yarwood, Chem. Mater., 1992, 4, 724-728;
88. (e) C. M. Yip and M. D. Ward, Langmuir, 1994, 10, 549-556;
89. (f) P. Cea, C. Lafuente, J. S. Urieta, M. C. López and F. M. Royo, Langmuir, 1997, 13, 4892-4897;
90. (g) Y. Urai, C. Ohe and K. Itoh, Langmuir, 1998, 14, 4873-4879;
91. (h) R. Yuge, A. Miyazaki, T. Enoki, K. Tamada, F. Nakamura and M. Hara, J. Phys. Chem. B, 2002, 106, 6894-6901;
92. (i) T. Akutagawa, M. Uchigata, T. Hasegawa, T. Nakamura, K. A. Nielsen, J. O. Jeppesen, T. Brimert and J. Becher, J. Phys. Chem. B, 2003, 107, 13929-13938;
93. (j) M. A. Herranz, L. Yu, N. Martin and L. Echegoyen, J. Org. Chem., 2003, 68, 8379-8385;
94. (k) H. Miyata, Y. Tatewaki, T. Akutagawa, T. Hasegawa, T. Nakamura, C. C. Christensen and J. Becher, Thin Solid Films, 2003, 438-439, 1-6;
95. (l) C. Jia, D. Zhang, Y. Xu, W. Xu and D. Zhu, Synth. Met., 2003, 137, 979-980;
96. (m) E. Dahlstedt, J. Hellberg, R. M. Petoral, Jr. and K. Uvdal, J. Mater. Chem., 2004, 14, 81-85.
97. (a) D. M. Cyr, B. Venkataraman and G. W. Flynn, Chem. Mater., 1996, 8, 1600-1615;
98. (b) C. L. Claypool, F. Faglioni, W. A. Goddard, III, H. B. Gray, N. S. Lewis and R. A. Marcus, J. Phys. Chem. B, 1997, 101, 5978-5995.
99. K. B. Simonsen, N. Svenstrup, J. Lau, O. Simonsen, P. Mork, G. J. Kristensen and J. Becher, Synthesis, 1996, 407-418.
100. C. U. Pittman, Jr., M. Narita and Y. F. Liang, J. Org. Chem., 1976, 41, 2855-2860.
101. N. Svenstrup, K. M. Rasmussen, T. K. Hansen and J. Becher, Synthesis, 1994, 809-812.
102. P. Wu, G. Saito, K. Imaeda, Z. Shi, T. Mori, T. Enoki and H. Inokuchi, Chem. Lett., 1986, 441-444.
103. (a) G. Steimecke, R. Kirmse and E. Hoyer, Z. Chem., 1975, 15, 28-29;
104. (b) G. Steimeche, H.-J. Sieler, R. Kirmse and E. Hoyer, Phosphorus, Sulfur Relat. Elem., 1979, 7, 49-55;
105. (c) R.-M. Olk, B. Olk, W. Dietzsch, R. Kirmse and E. Hoyer, Coord. Chem. Rev., 1992, 117, 99-131;
106. (d) T. K. Hansen, J. Becher, T. Jørgensen, K. S. Varma, R. Khedekar and M. P. Cava, Org. Synth., 1996, 73, 270-277.
107. P. R. Prag, J. D. Kilburn, M. C. Petty, C. Pearson and T. G. Ryan, Synthesis, 1994, 613-618.
108. (a) E. Fanghänel, L. van Hinh, G. Schukat and J. Patzsch, J. Prakt. Chem., 1989, 331, 479-485;
109. (b) M. Salle, A. Gorgues, M. Jubault, K. Boubekeur and P. Batail, Tetrahedron, 1992, 48, 3081-3090;
110. (c) M. Formigué, C. E. Uzelmeier, K. Boubekeur, S. L. Bartley and K. R. Dunbar, J. Organomet. Chem., 1997, 529, 343-350;
111. (d) R. Ballardini, V. Balzani, J. Becher, A. Di Fabio, M. T. Gandolfi, G. Mattersteig, M. B. Nielsen, F. M. Raymo, S. J. Rowan, J. F. Stoddart, A. J. P. White and D. J. Williams, J. Org. Chem., 2000, 65, 4120-4126.
112. A. Souizi, A. Robert, P. Batail and L. Ouahab, J. Org. Chem., 1987, 52, 1610-1611.
113. M. Vandevyver, M. Roulliay, J. P. Bourgoin, A. Barraud, V. Gionis, V. C. Kakoussis, G. A. Mousdis, J.-P. Morand and O. Noel, J. Phys. Chem., 1991, 95, 246-251.
114. M. Gonzalez, N. Martín and J. L. Segura, Tetrahedron Lett., 1998, 39, 3269-3272.
115. (a) S. Hünig and H. Berneth, Top. Curr. Chem., 1980, 92, 1-44;
116. (b) S. Sakura, H. Imai, H. Anzai and T. Moriya, Bull. Chem. Soc. Jpn., 1988, 61, 3181-3186;
117. (c) D. L. Lichtenberger, R. L. Johnston, K. Hinkelmann, T. Suzuki and F. Wudl, J. Am. Chem. Soc., 1990, 112, 3302-3307;
118. (d) M. Salle, M. Jubault, A. Gorgues, K. Boubekeur, M. Fourmigue, P. Batail and E. Canadell, Chem. Mater., 1993, 5, 1196-1198;
119. (e) M. Salle, A. J. Moore, M. R. Bryce and M. Jubault, Tetrahedron Lett., 1993, 34, 7475-7478;
120. (f) C. Rovira, J. Veciana, N. Santal, J. Tarres, J. Cirujeda, E. Molins, J. Llorca and E. Espinosa, J. Org. Chem., 1994, 59, 3307-3313;
121. (g) A. S. Batsanov, M. R. Bryce, J. N. Heaton, A. J. Moore, P. J. Skabara, J. A. K. Howard, E. Orti, P. M. Viruela and R. Viruela, J. Mater. Chem., 1995, 5, 1689-1696;
122. (h) E. Ribera, J. Veciana, E. Molins, I. Mata, K. Wurst and C. Rovira, Eur. J. Org. Chem., 2000, 2867-2875.
123. The cyclic voltammetry of compounds with very long alkyl chains can give rise to irreversible processes, although the dodecyl derivatives are well-behaved. See: P. Cea, J. I. Pardo, J. S. Urieta, M. C. Lopez and F. M. Royo, Electrochim. Acta, 2000, 46, 589-597.
124. (a) G. Saito, T. Teramoto, A. Otsuka, Y. Sugita, T. Ban, M. Kusunoki and K.-I. Sakaguchi, Synth. Met., 1994, 64, 359-368;
125. (b) J. Llacay, J. Tarrés, C. Rovira, J. Veciana, M. Mas and E. Molins, J. Phys. Chem. Solids, 1997, 58, 1675-1678;
126. (c) D. V. Konarev, E. F. Valeev, Yu. L. Slovokhotov, Yu. M. Shul'ga, O. S. Roschupkina and R. N. Lyubovskaya, Synth. Met., 1997, 88, 85-87;
127. (d) D. V. Konarev, A.Yu. Kovalevsky, P. Coppens and R. N. Lyubovskaya, Chem. Commun., 2000, 2357-2358;
128. (e) D. V. Konarev, R. N. Lyubovskaya, N. V. Drichko, E. I. Yudanova, Y. M. Shul'ga, A. L. Litvinov, V. N. Semkin and B. P. Tarasov, J. Mater. Chem., 2000, 10, 803-818;
129. (f) D. V. Konarev, I. S. Neretin, Y. L. Slovokhotov, A. L. Litvinov, A. Otsuka, R. N. Lyubovskaya and G. N. Saito, Synth. Met., 2002, 131, 87-92.
130. D. Hadzi and S. Detoni, in The Chemistry of Acid Derivatives, Part 1, ed. S. Patai, J. Wiley & Sons, New York, 1992.
131. STM measurements of 23 under (presumably) dry conditions revealed apparent stacks: J. Lu, Q.-d. Zeng, C. Wang, L.-J. Wan and C.-L. Bai, Chem. Lett., 2003, 32, 856-857.
132. (d) A. Janiak, J. Chem. Soc., Dalton Trans., 2000, 3885-3896;
133. (b) C. A. Hunter, K. R. Lawson, J. Perkins and C. J. Urch, J. Chem. Soc., Perkin Trans. 2, 2001, 651-669;
134. (c) G. Lincke, Dyes Pigm., 2003, 59, 1-24.
135. T. Yokoyama, S. Yokoyama, T. Kamikado, Y. Okuno and S. Mashiko, Nature, 2001, 413, 619-621.
136. A. K. Rappé, C. J. Casewit, K. S. Colwell, W. A. Goddard, III and W. M. Skiff, J. Am. Chem. Soc., 1992, 114, 10024-10035.
137. C. J. Casewit, K. S. Coldwell and A. K. Rappé, J. Am. Chem. Soc., 1992, 114, 10035-10046.