Altering the static dipole on surfaces through chemistry: Molecular films of zwitterionic quinonoids

Journal of the American Chemical Society

Volumn 134, Issue 20, 2012, Pages 8494-8506

  Routaboul, Lucie ^a   Braunstein, Pierre ^a   Xiao, Jie ^b   Zhang, Zhengzheng ^b   Dowben, Peter A ^b   Dalmas, Guillaume ^a   Da Costa, Victor ^a   Félix, Olivier ^a   Decher, Gero ^a   Rosa, Luis G ^c   Doudin, Bernard ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITY OF NEBRASKA LINCOLN   (United States)

^c UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

CLOSE PACKED; CONDUCTION-BAND MINIMUM; DIPOLAR MOLECULES; ELECTRICAL DIPOLES; HIGH CONDUCTIVITY; INTERFACE DIPOLE; META POSITIONS; METAL ELECTRODES; METAL-ORGANIC INTERFACE; MOLECULAR FILMS; ORGANIC ELECTRONICS; PREFERENTIAL ADSORPTION; QUINONOIDS; SELF-ASSEMBLED; SELF-ASSEMBLING; SINGLE CRYSTAL X-RAY DIFFRACTION; SMALL MOLECULES; SPECTROSCOPIC PROPERTY; STATIC DIPOLE; ZWITTER IONIC MOLECULE;

ADSORPTION; GOLD; MOLECULES; SINGLE CRYSTALS; X RAY DIFFRACTION;

INTERFACES (MATERIALS);

AMPHOLYTE; BENZOQUINONE DERIVATIVE; GOLD; NANOFILM; NITROGEN; OXYGEN;

ADSORPTION; ARTICLE; CRYSTAL STRUCTURE; DIPOLE; ELECTRIC CONDUCTIVITY; ELECTRODE; ELECTRON; MOLECULAR DYNAMICS; MOLECULAR ELECTRONICS; MOLECULAR STABILITY; NANOENGINEERING; SPECTROSCOPY; STATIC ELECTRICITY; SURFACE CHARGE; X RAY DIFFRACTION;

EID: 84861373217     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja212104b     Document Type: Article

References (113)

1. Braun, S.; Salaneck, W. R.; Fahlman, M. Adv. Mater. 2009, 21, 1450-1472
2. Karthäuser, S. J. Phys.: Condens. Matter 2011, 23, 013001
3. Ma, H.; Yip, H.-L.; Huang, F.; Jen, A. K.-Y. Adv. Funct. Mater. 2010, 20, 1371-1388
4. Hill, I. G.; Rajagopal, A.; Kahn, A.; Hu, Y. Appl. Phys. Lett. 1998, 73, 662-664
5. Ishii, H.; Sugiyama, K.; Ito, E.; Seki, K. Adv. Mater. 1999, 11, 605-625
6. Zhu, X. Y. Surf. Sci. Rep. 2004, 56, 1-83
7. Koch, N.; Elschner, N.; Schwartz, J.; Kahn, A. Appl. Phys. Lett. 2003, 82, 2281-2883
8. Kera, S.; Yabuuchi, Y.; Yamane, H.; Setoyama, H.; Okudaira, K. K.; Kahn, A.; Ueno, N. Phys. Rev. B 2004, 70, 085304/1-085304/6
9. Dowben, P. A.; Rosa, L. G.; Ilie, C. C.; Xiao, J. J. Electron Spectrosc. Relat. Phenom. 2009, 174, 10-21
10. L'vov, V. S.; Naaman, R.; Tiberkevich, V.; Vager, Z. Chem. Phys. Lett. 2003, 381, 650-653
11. Cahen, D.; Naaman, R.; Vager, Z. Adv. Funct. Mater. 2005, 15, 1571-1578
12. Balaz, S.; Caruso, A. N.; Platt, N. P.; Dimov, D. I.; Boag, N. M.; Brand, J. I.; Losovyj, Y. B.; Dowben, P. A. J. Phys. Chem. B 2007, 111, 7009-7016
13. Barraud, C.; Seneor, P.; Mattana, R.; Fusil, S.; Bouzehouane, K.; Deranlot, C.; Graziosi, P.; Hueso, L.; Bergenti, I.; Dediu, V.; Petroff, P; Fert, A. Nat. Phys. 2010, 6, 615-620
14. Yuan, Y.; Reece, T. J.; Sharma, P.; Poddar, S.; Ducharme, S.; Gruverman, A.; Yang, Y.; Huang, J. Nat. Mater. 2011, 10, 296-302
15. Sawicka, A.; Skurski, P.; Simons, J. Chem. Phys. Lett. 2002, 362, 527-533
16. Haas, Y.; Zilberg, S. J. Am. Chem. Soc. 2004, 126, 8991-8998
17. Siri, O.; Braunstein, P. Chem. Commun. 2002, 208-209
18. Braunstein, P.; Siri, O.; Taquet, J.-P.; Rohmer, M.-M.; Bénard, M.; Welter, R. J. Am. Chem. Soc. 2003, 125, 12246-12256
19. Braunstein, P.; Siri, O.; Steffanut, P.; Winter, M.; Yang, Q.-Z. C. R. Chim. 2006, 9, 1493-1499
20. Braunstein, P.; Siri, O.; Taquet, J.-p.; Yang, Q.-Z. Angew. Chem., Int. Ed. 2006, 45, 1393-1397
21. Taquet, J.-p.; Siri, O.; Braunstein, P.; Welter, R. Inorg. Chem. 2004, 43, 6944-6953
22. Yang, Q.-Z.; Kermagoret, A.; Agostinho, M.; Siri, O.; Braunstein, P. Organometallics 2006, 25, 5518-5527
23. Yang, Q.-Z.; Siri, O.; Braunstein, P. Chem. Commun. 2005, 2660-2662
24. Yang, Q.-Z.; Siri, O.; Brisset, H.; Braunstein, P. Tetrahedron Lett. 2006, 47, 5727-5731
25. Yang, Q.-Z.; Siri, O.; Braunstein, P. Chem.-Eur. J. 2005, 11, 7237-7246
26. Xiao, J.; Zhang, Z.; Wu, D.; Routaboul, L.; Braunstein, P.; Doudin, B.; Losovyj, Y. B.; Kizilkaya, O.; Rosa, L. G.; Borca, C. N.; Gruverman, A.; Dowben, P. A. Phys. Chem. Chem. Phys. 2010, 12, 10329-10340
27. Lu, X.; Hipps, K. W.; Wang, X. D.; Mazur, U. J. Am. Chem. Soc. 1996, 118, 7197-7202
28. Xiao, J.; Dowben, P. A. J. Mater. Chem. 2009, 19, 2172-2178
29. Dowben, P. A.; Xiao, J.; Xu, B.; Sokolov, A.; Doudin, B. Appl. Surf. Sci. 2008, 254, 4238-424
30. Fang, Y.; Nguyen, P.; Ivasenko, O.; Aviles, M. P.; Kebede, E.; Askari, M. S.; Ottenwaelder, X.; Ziener, U.; Siri, O.; Cuccia, L. A. Chem Commun. 2011, 47, 11255-11257
31. Zhang, Z.; Alvira, J.; Barbosa, X.; Rosa, L. G.; Routaboul, L.; Braunstein, P.; Doudin, B.; Dowben, P. A. J. Phys. Chem. C 2011, 115, 2812-2818
32. Kappa CCD Operation Manual; Nonius BV: Delft, The Netherlands, 1997; Sheldrick, G. M. SHELXL97, Program for the Refinement of Crystal Structures; University of Gottingen, Germany, 1997.
33. Dowben, P. A; Miller, A., Eds.; Surface Segregation Phenomena; CRC Press: Boston, MA, 1990; p 145
34. Cumpson, P. J. J. Electron Spectrosc. Relat. Phenom. 1995, 73, 25-52
35. Jablonski, A.; Powell, C. J. Surf. Sci. Rep. 2002, 47, 33
36. Tanuma, S.; Powell, C. J.; Penn, D. R. Scanning 2006, 28, 112-113
37. Hajati, S.; Coultas, S.; Blornfield, C.; Tougaard, S. Surf. Interface Anal. 2008, 40, 688-691
38. Hajati, S.; Tougaard, S. Anal. Bioanal. Chem. 2010, 396, 2741-2755
39. Tougaard, S.; Jablonski, A. J. Vac. Sci. Technol., A 2011, 29, 051401
40. Kizilkaya, O.; Scott, J. D.; Morikawa, E.; Garber, J. D.; Perkins, R. S. Rev. Sci. Instrum. 2005, 76, 13703
41. Kizilkaya, O.; Prange, A.; Steiner, U.; Oerke, E. C.; Scott, J. D.; Morikawa, E.; Hormes, J. Nucl. Instrum. Methods Phys. Res., Sect. A 2007, 582, 274-276
42. Delley, B. J. Chem. Phys. 1990, 92, 508
43. Delley, B. J. Chem. Phys. 2000, 113, 7756
44. Vericat, C.; Vela, M. E.; Benitez, G. A.; Gago, J. A. M.; Torrelles, X.; Salvarezza, R. C. J. Phys.: Condens. Matter 2006, 18, R867-R900
45. Vericat, C; Vela, M. E.; Andreasen, G.; Salvarezza, R. C.; Vazquez, L.; Marin-Gago, J. A. Langmuir 2001, 17, 4919-4924
46. Kriegisch, V.; Lambert, C. Top. Curr. Chem. 2005, 258, 257-313
47. Tao, F.; Bernasek, S. L. Chem. Rev. 2007, 107, 1408-1453
48. Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzzo, R. G.; Whitesides, G. M. Chem. Rev. 2005, 105, 1103-1169
49. Nuzzo, R. G.; Allara, D. L. J. Am. Chem. Soc. 1983, 105, 4481-4483
50. Nuzzo, R. G.; Zegarski, B. R.; Dubois, L. H. J. Am. Chem. Soc. 1987, 109, 733-40
51. Vericat, C.; Vela, M. E.; Benitez, G.; Carro, P.; Salvarezza, R. C. Chem. Soc. Rev. 2010, 39, 1805-1834
52. Weidner, T.; Kraemer, A.; Bruhn, C.; Zharnikov, M.; Shaporenko, A.; Siemeling, U.; Traeger, F. Dalton Trans. 2006, 2767-2777
53. Mannini, M.; Sorace, L.; Gorini, L.; Piras, F. M.; Caneschi, A.; Magnani, A.; Menichetti, S.; Gatteschi, D. Langmuir 2007, 23, 2389-2397
54. Noh, J.; Jeong, Y.; Ito, E.; Hara, M. J. Phys. Chem. C 2007, 111, 2691-2695
55. Jian, H.; Tour, J. M. J. Org. Chem. 2003, 68, 5091-5103
56. Cavalleri, O.; Vignolo, M.; Strano, G.; Natale, C.; Rolandi, R.; Thea, S.; Prato, M.; Gonella, G.; Canepa, M.; Gliozzi, A. Bioelectrochemistry 2004, 63, 3-7
57. Tierney, H. L.; Baber, A. E.; Sykes, E. C. H.; Akimov, A.; Kolomeisky, A. B. J. Phys. Chem. C 2009, 113, 10913-10920
58. Baber, A. E.; Tierney, H. L.; Sykes, E. C. H. ACS Nano 2008, 2, 2385-2391
59. Menozzi, E.; Pinalli, R.; Speets, E. A.; Ravoo, B. J.; Dalcanale, E.; Reinhoudt, D. N. Chem.-Eur. J. 2004, 10, 2199-2206
60. Zhang, S.; Echegoyen, L. Tetrahedron 2006, 62, 1947-1954
61. Mannini, M.; Rovai, D.; Sorace, L.; Perl, A.; Ravoo, B. J.; Reinhoudt, D. N.; Caneschi, A. Inorg. Chim. Acta 2008, 361, 3525-3528
62. Jewell, A. D.; Tierney, H. L.; Baber, A. E.; Iski, E. V.; Laha, M. M.; Sykes, E. C. H. J. Phys.: Condens. Matter 2010, 22, 264006/1-264006/11
63. Bellisario, D. O.; Jewell, A. D.; Tierney, H. L.; Baber, A. E.; Sykes, E. C. H. J. Phys. Chem. C 2010, 114, 14583-14589
64. Tierney, H. L.; Jewell, A. D.; Baber, A. E.; Iski, E. V.; Sykes, E. C. H. Langmuir 2010, 26, 15350-15355
65. Zharnikov, M; Golzhauser, A.; Grunze, M. Appl. Phys. Lett. 1999, 75, 2401-2403
66. Dezarnaud, C.; Tronc, M.; Modelli, A. Chem. Phys. 1991, 156, 129-140
67. Zoloff Michoff, M. E.; Velez, P.; Leiva, E. P. M J. Phys. Chem. C 2009, 113, 3850-3854
68. Iori, F.; Corni, S.; Di Felice, R. J. Phys. Chem. C 2008, 112, 13540-13545
69. Cafe, P. F.; Larsen, A. G.; Yang, W.; Bilic, A.; Blake, I. M.; Crossley, M. J.; Zhang, J.; Wackerbarth, H.; Ulstrup, J.; Reimers, J. R. J. Phys. Chem. C 2007, 111, 17285-17296
70. Gong, J.; Yan, T.; Mullins, C. B. Chem. Commun. 2009, 761-763
71. Sivanesan, A.; John, S. A. Langmuir 2008, 24, 2186-2190
72. Barber, M.; Conner, J. A.; Guest, M. F.; Hillier, I. H.; Schwarz, M.; Stacy, M. J. Chem. Soc., Faraday Trans. 2 1973, 69, 551-558
73. Lindberg, B. J.; Hedman, J. Chem. Scr. 1975, 7, 155-166
74. Yoshida, T.; Sawada, S. Bull. Chem. Soc. Jpn. 1974, 47, 50-53
75. Yatsimirskii, K. B.; Nemoshalenko, V. V.; Aleshin, V. G.; Bratushko, Y. I.; Moiseenko, E. P. Chem. Phys. Lett. 1977, 52, 481-484
76. Lindberg, B. J.; Hamrin, K.; Johansson, G.; Gelius, V.; Falhlmann, A.; Nordling, C.; Siegbahn, K. Phys. Scr. 1970, 1, 286-298
77. Block, E. Reactions of Organosulfur Compounds; Academic Press: New York, 1978.
78. Sato, N.; Seki, K.; Inokuchi, H. J. J. Chem. Soc., Faraday Trans. 2 1981, 77, 1621-1633
79. Fukagawa, H.; Yamane, H.; Kataoka, T.; Kera, S.; Nakamura, M.; Kudo, K.; Ueno, N. Phys. Rev. B 2006, 73, 245310/1-245310/5
80. Schroeder, P. G.; France, C. B.; Park, J. B.; Parkinson, B. A. J. Phys. Chem. B 2003, 107, 2253-2261
81. Rosa, L. G.; Velev, J.; Zhang, Z.; Alvira, J.; Vega, O.; Diaz, G.; Routaboul, L.; Braunstein, P.; Doudin, B.; Losovyj, Ya. B.; Dowben, P. A. Phys. Status Solidi B 2012, DOI: 10.1002/pssb.201147426.
82. Ortega, J. E.; Himpsel, F. J.; Li, D.; Dowben, P. A. Solid State Commun. 1994, 91, 807
83. Dowben, P. A. Surf. Sci. Rep. 2000, 40, 151-247
84. Chua, L.-L.; Zaumseil, J.; Chang, J.-F.; Ou, E. C.-W.; Ho, P. K.-H.
85. Sirringhaus, H.; Friend, R. H. Nature 2005, 434, 194-199
86. Kümmel, S.; Kronik, L. Rev. Mod. Phys. 2008, 80, 3-60
87. Bechstedt, F.; Fuchs, F.; Kresse, G. Phys. State Solidi B 2009, 246, 1877-1892
88. Stein, T.; Kronik, L.; Baer, R. J. Am. Chem. Soc. 2009, 131, 2818
89. Liao, M.-S.; Lu, Y.
90. Scheiner, S. J. Comput. Chem. 2003, 24, 623-631
91. Yakovkin, I. N.; Dowben, P. A. Surf. Rev. Lett. 2007, 14, 481-487
92. Dowben, P. A.; Xu, B.; Choi, J.; Morikawa, E. Handb. Thin Film Mater. 2002, 2, 61-113
93. Plummer, E. W.; Eberhardt, W. Adv. Chem. Phys. 1982, 49, 533-656
94. Steinrück, H.-P. Vacuum 1994, 45, 715-731
95. Lunca Popa, P.; Dalmas, G.; Faramarzi, V.; Dayen, J. F.; Majjad, H.; Kemp, N. T.; Doudin, B. Nanotechnology 2011, 22, 215302
96. Akkerman, H. B.; de Boer, B. J. Phys.: Condens. Matter 2008, 20, 013001
97. Doudin, B.; Braunstein, P.; Routaboul, L.; Dalmas, G.; Zhang, Z.; Dowben, P. Patent WO 2012025878 A1 to CNRS.
98. Britton, A. J.; Rienzo, A.; O'Shea, J. N.; Schulte, K. J. Chem. Phys. 2010, 133, 094705/1-094705/7
99. Chen, W.-K.; Cao, M.-J.; Liu, S.-H.; Lu, C.-H.; Xu, Y.; Li, J.-Q. Chem. Phys. Lett. 2006, 417, 414-418
100. Gao, P.; Weaver, M. J. J. Phys. Chem. 1985, 89, 5040-5046
101. Schuster, C.; Schwingenschloegl, U. Chem. Phys. Lett. 2009, 468, 75-78
102. Syomin, D.; Kim, J.; Koel, B. E.; Ellison, G. B. J. Phys. Chem. B 2001, 105, 8387-8394
103. Brede, J.; Linares, M.; Kuck, S.; Schwoebel, J.; Scarfato, A.; Chang, S.-H.; Hoffmann, G.; Wiesendanger, R.; Lensen, R.; Kouwer, P. H. J.; Hoogboom, J.; Rowan, A. E.; Bröring, M.; Funk, M.; Stafström, S.; Zerbetto, F.; Lazzaroni, R. Nanotechnology 2009, 20, 275602/1-275602/10
104. Guaino, P.; Carty, D.; Hughes, G.; McDonald, O.; Cafolla, A. A. Appl. Phys. Lett. 2004, 85, 2777-2779
105. Han, B.; Li, Z.; Wandlowski, T.; Blaszczyk, A.; Mayor, M. J. Phys. Chem. C 2007, 111, 13855-13863
106. Huang, T.; Hu, Z.; Zhao, A.; Wang, H.; Wang, B.; Yang, J.; Hou, J. G. J. Am. Chem. Soc. 2007, 129, 3857-3862
107. Jiang, P.; Deng, K.; Fichou, D.; Xie, S.-S.; Nion, A.; Wang, C. Langmuir 2009, 25, 5012-5017
108. Langlais, V. A.; Gauthier, Y.; Belkhir, H.; Maresca, O. Phys. Rev. B 2005, 72, 085444/1-085444/7
109. Lux, F.; Lemercier, G.; Andraud, C.; Schull, G.; Charra, F. Langmuir 2006, 22, 10874-10876
110. Pinheiro, L. S.; Temperini, M. L. A. Surf. Sci. 2000, 464, 176-182
111. Sakai, N.; Sisson, A. L.; Buergi, T.; Matile, S. J. Am. Chem. Soc. 2007, 129, 15758-15759
112. Sisson, A. L.; Sakai, N.; Banerji, N.; Fuerstenberg, A.; Vauthey, E.; Matile, S. Angew. Chem., Int. Ed. 2008, 47, 3727-3729
113. Tulevski, G. S.; Bushey, M. L.; Kosky, J. L.; Ruter, S. J. T.; Nuckolls, C. Angew. Chem., Int. Ed. 2004, 43, 1836-1839