Organic/metal interfaces in self-assembled monolayers of conjugated thiols: A first-principles benchmark study

Surface Science

Volumn 600, Issue 19, 2006, Pages 4548-4562

  Heimel, Georg ^a   Romaner, Lorenz ^a,b   Brédas, Jean Luc ^a   Zojer, Egbert ^a,b  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

Aromatics; Density functional calculations; Interface dipole; Metal semiconductor interfaces; Molecular electronics; Organic molecules; Self assembled; Thiols

Indexed keywords

FERMI LEVEL; MOLECULAR STRUCTURE; MONOLAYERS; PROBABILITY DENSITY FUNCTION; SELF ASSEMBLY; SUBSTRATES; SULFUR COMPOUNDS;

AROMATICS; INTERFACE DIPOLE; METAL-SEMICONDUCTOR INTERFACES; MOLECULAR ELECTRONICS; ORGANIC MOLECULES; SINGLE-MOLECULE ELECTRONICS; THIOLS;

INTERFACES (MATERIALS);

EID: 33749064719     PISSN: 00396028     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.susc.2006.07.023     Document Type: Article

References (151)

1. Love J.C., Estroff L.A., Kriebel J.K., Nuzzo R.G., and Whitesides G.M. Chem. Rev. 105 (2005) 1103
2. Poirier G.E. Chem. Rev. 97 (1997) 1117
3. Schreiber F. Prog. Surf. Sci. 65 (2000) 151
4. Schreiber F. J. Phys.: Condens. Matter 16 (2004) R881
5. Schwartz D.K. Annu. Rev. Phys. Chem. 52 (2001) 107
6. Ulman A. Chem. Rev. 96 (1996) 1533
7. Eck W., Stadler V., Geyer W., Zharnikov M., Gölzhäuser A., and Grunze M. Adv. Mater. 12 (2000) 805
8. Felgenhauer T., Yan C., Geyer W., Rong H.T., Gölzhäuser A., and Buck M. Appl. Phys. Lett. 79 (2001) 3323
9. Geyer W., Stadler V., Eck W., Zharnikov M., Gölzhäuser A., and Grunze M. Appl. Phys. Lett. 75 (1999) 2401
10. Gooding J.J., Mearns F., Yang W.R., and Liu J.Q. Electroanalysis 15 (2003) 81
11. Kleineberg U., Brechling A., Sundermann M., and Heinzmann U. Adv. Funct. Mater. 11 (2001) 208
12. Halik M., Klauk H., Zschieschang U., Schmid G., Dehm C., Schütz M., Maisch S., Effenberger F., Brunnbauer M., and Stellacci F. Nature 431 (2004) 963
13. Kobayashi S., Nishikawa T., Takenobu T., Mori S., Shimoda T., Mitani T., Shimotani H., Yoshimoto N., Ogawa S., and Iwasa Y. Nat. Mater. 3 (2004) 317
14. Genzer J., and Efimenko K. Science 290 (2000) 2130
15. Jennings G.K., and Laibinis P.E. Colloids Surf., A 116 (1996) 105
16. Campbell I.H., Kress J.D., Martin R.L., Smith D.L., Barashkov N.N., and Ferraris J.P. Appl. Phys. Lett. 71 (1997) 3528
17. Campbell I.H., Rubin S., Zawodzinski T.A., Kress J.D., Martin R.L., Smith D.L., Barashkov N.N., and Ferraris J.P. Phys. Rev. B 54 (1996) 14321
18. de Boer B., Hadipour A., Mandoc M.M., van Woudenbergh T., and Blom P.W.M. Adv. Mater. 17 (2005) 621
19. Ganzorig C., Kwak K.J., Yagi K., and Fujihira M. Appl. Phys. Lett. 79 (2001) 272
20. Hatton R.A., Day S.R., Chesters M.A., and Willis M.R. Thin Solid Films 394 (2001) 292
21. Yan H., Huang Q.L., Cui J., Veinot J.G.C., Kern M.M., and Marks T.J. Adv. Mater. 15 (2003) 835
22. Zehner R.W., Parsons B.F., Hsung R.P., and Sita L.R. Langmuir 15 (1999) 1121
23. Zuppiroli L., Si-Ahmed L., Kamaras K., Nüesch F., Bussac M.N., Ades D., Siove A., Moons E., and Grätzel M. Eur. J. Phys. B 11 (1999) 505
24. Alloway D.M., Hofmann M., Smith D.L., Gruhn N.E., Graham A.L., Colorado R., Wysocki V.H., Lee T.R., Lee P.A., and Armstrong N.R. J. Phys. Chem. B 107 (2003) 11690
25. Ishii H., Sugiyama K., Ito E., and Seki K. Adv. Mater. 11 (1999) 605
26. Kahn A., Koch N., and Gao W.Y. J. Polym. Sci., Part B 41 (2003) 2529
27. Chen J., Reed M.A., Rawlett A.M., and Tour J.M. Science 286 (1999) 1550
28. Elbing M., Ochs R., Koentopp M., Fischer M., von Hänisch C., Weigend F., Evers F., Weber H.B., and Mayor M. Proc. Natl. Acad. Sci. 102 (2005) 8815
29. Jiang P., Morales G.M., You W., and Yu L.P. Angew. Chem. Int. Ed. 43 (2004) 4471
30. Kushmerick J.G., Holt D.B., Yang J.C., Naciri J., Moore M.H., and Shashidhar R. Phys. Rev. Lett. 89 (2002) 086802
31. Park J., et al. Nature 417 (2002) 722
32. Reed M.A., Chen J., Rawlett A.M., Price D.W., and Tour J.M. Appl. Phys. Lett. 78 (2001) 3735
33. Patrone L., Palacin S., Charlier J., Armand F., Bourgoin J.P., Tang H., and Gauthier S. Phys. Rev. Lett. 91 (2003) 096802
34. Xue Y.Q., and Ratner M.A. Phys. Rev. B 68 (2003) 115407
35. Yaliraki S.N., Kemp M., and Ratner M.A. J. Am. Chem. Soc. 121 (1999) 3428
36. Amlani I., Rawlett A.M., Nagahara L.A., and Tsui R.K. Appl. Phys. Lett. 80 (2002) 2761
37. Böhler T., Grebing J., Mayer-Gindner A., Löhneysen H.V., and Scheer E. Nanotechnology 15 (2004) S465
38. Hong S.H., Kim H.K., Kim B.C., Choi Y.S., Hwang J.S., Ahn D., Kwak S.K., Ahn D.J., and Hwang S.W. J. Korean Phys. Soc. 45 (2004) S665
39. Long D.P., Patterson C.H., Moore M.H., Seferos D.S., Bazan G.C., and Kushmerick J.G. Appl. Phys. Lett. 86 (2005) 153105
40. Nazin G.V., Qiu X.H., and Ho W. Science 302 (2003) 77
41. Zareie M.H., Ma H., Reed B.W., Jen A.K.Y., and Sarikaya M. Nano Lett. 3 (2003) 139
42. Zhou C., Deshpande M.R., Reed M.A., Jones L., and Tour J.M. Appl. Phys. Lett. 71 (1997) 611
43. Zhou C., Muller C.J., Deshpande M.R., Sleight J.W., and Reed M.A. Appl. Phys. Lett. 67 (1995) 1160
44. Ghosh A.W., Zahid F., Datta S., and Birge R.R. Chem. Phys. 281 (2002) 225
45. Xue Y.Q., Datta S., and Ratner M.A. J. Chem. Phys. 115 (2001) 4292
46. Xue Y.Q., and Ratner M.A. Phys. Rev. B 68 (2003) 115406
47. Xue Y.Q., and Ratner M.A. Phys. Rev. B 69 (2004) 085403
48. Grönbeck H., Curioni A., and Andreoni W. J. Am. Chem. Soc. 122 (2000) 3839
49. Morikawa Y., Hayashi T., Liew C.C., and Nozoye H. Surf. Sci. 507 (2002) 46
50. Vargas M.C., Giannozzi P., Selloni A., and Scoles G. J. Phys. Chem. B 105 (2001) 9509
51. Yourdshahyan Y., and Rappe A.M. J. Chem. Phys. 117 (2002) 825
52. Hayashi T., Morikawa Y., and Nozoye H. J. Chem. Phys. 114 (2001) 7615
53. Gottschalck J., and Hammer B. J. Chem. Phys. 116 (2002) 784
54. Yourdshahyan Y., Zhang H.K., and Rappe A.M. Phys. Rev. B 6308 (2001) 081405
55. Bilic A., Reimers J.R., and Hush N.S. J. Chem. Phys. 122 (2005) 094708
56. Nara J., Higai S., Morikawa Y., and Ohno T. J. Chem. Phys. 120 (2004) 6705
57. Sun Q., Selloni A., and Scoles G. J. Phys. Chem. B 110 (2006) 3493
58. McNally H., Janes D.B., Kasibhatla B., and Kubiak C.P. Superlattices Microstruct. 31 (2002) 239
59. Azzam W., Fuxen C., Birkner A., Rong H.T., Buck M., and Wöll C. Langmuir 19 (2003) 4958
60. Leung T.Y.B., Schwartz P., Scoles G., Schreiber F., and Ulman A. Surf. Sci. 458 (2000) 34
61. Dhirani A.A., Zehner R.W., Hsung R.P., Guyot-Sionnest P., and Sita L.R. J. Am. Chem. Soc. 118 (1996) 3319
62. Duan L., and Garrett S.J. J. Phys. Chem. B 105 (2001) 9812
63. Fuxen C., Azzam W., Arnold R., Witte G., Terfort A., and Wöll C. Langmuir 17 (2001) 3689
64. Ishida T., Mizutani W., Azehara H., Miyake K., Aya Y., Sasaki S., and Tokumoto H. Surf. Sci. 514 (2002) 187
65. Tao Y.T., Wu C.C., Eu J.Y., Lin W.L., Wu K.C., and Chen C.H. Langmuir 13 (1997) 4018
66. Yang G.H., and Liu G.Y. J. Phys. Chem. B 107 (2003) 8746
67. Azzam W., Cyganik P., Witte G., Buck M., and Wöll C. Langmuir 19 (2003) 8262
68. Cyganik P., Buck M., Azzam W., and Wöll C. J. Phys. Chem. B 108 (2004) 4989
69. Ishida T., Mizutani W., Akiba U., Umemura K., Inoue A., Choi N., Fujihira M., and Tokumoto H. J. Phys. Chem. B 103 (1999) 1686
70. Kang J.F., Jordan R., and Ulman A. Langmuir 14 (1998) 3983
71. Kang J.F., Liao S., Jordan R., and Ulman A. J. Am. Chem. Soc. 120 (1998) 9662
72. Kang J.F., Ulman A., Liao S., and Jordan R. Langmuir 15 (1999) 2095
73. Kang J.F., Ulman A., Liao S., Jordan R., Yang G.H., and Liu G.Y. Langmuir 17 (2001) 95
74. Shaporenko A., Heister K., Ulman A., Grunze M., and Zharnikov M. J. Phys. Chem. B 109 (2005) 4096
75. Fenter P., Schreiber F., Berman L., Scoles G., Eisenberger P., and Bedzyk M.J. Surf. Sci. 413 (1998) 213
76. Yeganeh M.S., Dougal S.M., Polizzotti R.S., and Rabinowitz P. Phys. Rev. Lett. 74 (1995) 1811
77. Barth J.V., Brune H., Ertl G., and Behm R.J. Phys. Rev. B 42 (1990) 9307
78. Harten U., Lahee A.M., Toennies J.P., and Wöll C. Phys. Rev. Lett. 54 (1985) 2619
79. Huang K.G., Gibbs D., Zehner D.M., Sandy A.R., and Mochrie S.G.J. Phys. Rev. Lett. 65 (1990) 3313
80. Sandy A.R., Mochrie S.G.J., Zehner D.M., Huang K.G., and Gibbs D. Phys. Rev. B 43 (1991) 4667
81. Takeuchi N., Chan C.T., and Ho K.M. Phys. Rev. B 43 (1991) 13899
82. Wöll C., Chiang S., Wilson R.J., and Lippel P.H. Phys. Rev. B 39 (1989) 7988
83. Blöchl P.E. Phys. Rev. B 50 (1994) 17953
84. Kresse G., and Joubert D. Phys. Rev. B 59 (1999) 1758
85. Kresse G., and Furthmüller J. Phys. Rev. B 54 (1996) 11169
86. Tsuzuki S., and Lüthi H.P. J. Chem. Phys. 114 (2001) 3949
87. Monkhorst H.J., and Pack J.D. Phys. Rev. B 13 (1976) 5188
88. Methfessel M., and Paxton A.T. Phys. Rev. B 40 (1989) 3616
89. Puschnig P., and Ambrosch-Draxl C. Phys. Rev. B 60 (1999) 7891
90. Neugebauer J., and Scheffler M. Phys. Rev. B 46 (1992) 16067
91. Methfessel M., Fiorentini V., and Oppo S. Phys. Rev. B 61 (2000) 5229
92. Vackar J., Hytha M., and Simunek A. Phys. Rev. B 58 (1998) 12712
93. Tersoff J. Phys. Rev. B 40 (1989) 11990
94. Tersoff J., and Hamann D.R. Phys. Rev. Lett. 50 (1983) 1998
95. Tersoff J., and Hamann D.R. Phys. Rev. B 31 (1985) 805
96. Khein A., Singh D.J., and Umrigar C.J. Phys. Rev. B 51 (1995) 4105
97. Yu B.D., and Scheffler M. Phys. Rev. B 56 (1997) R15569
98. Chiarotti G. In: Börnstein L. (Ed). Numerical Data and Functional Relationships in Science and Technology - New Series, Group III Condensed Matter vol. 24a (1993), Springer, Heidelberg 21
99. Anderson O.L., Isaak D.G., and Yamamoto S. J. Appl. Phys. 65 (1989) 1534
100. Daniels W.B., and Smith C.S. Phys. Rev. 111 (1958) 713
101. Golding B., Moss S.C., and Averbach B.L. Phys. Rev. 158 (1967) 637
102. Heinz D.L., and Jeanloz R. J. Appl. Phys. 55 (1984) 885
103. Kittel C. Introduction to Solid State Physics. third ed. (1976), John Wiley & Sons, Inc., New York
104. Neighbours J.R., and Alers G.A. Phys. Rev. 111 (1958) 707
105. Needs R.J., and Mansfield M. J. Phys.: Condens. Matter 1 (1989) 7555
106. Tyson W.R., and Miller W.A. Surf. Sci. 62 (1977) 267
107. Vitos L., Ruban A.V., Skriver H.L., and Kollar J. Surf. Sci. 411 (1998) 186
108. Wan J., Fan Y.L., Gong D.W., Shen S.G., and Fan X.Q. Modell. Simul. Mater. Sci. Eng. 7 (1999) 189
109. Galanakis I., Bihlmayer G., Bellini V., Papanikolaou N., Zeller R., Blugel S., and Dederichs P.H. Europhys. Lett. 58 (2002) 751
110. Galanakis I., Papanikolaou N., and Dederichs P.H. Surf. Sci. 511 (2002) 1
111. Skriver H.L., and Rosengaard N.M. Phys. Rev. B 46 (1992) 7157
112. Eastman D.E. Phys. Rev. B 2 (1970) 1
113. Hansson G.V., and Flodström S.A. Phys. Rev. B 18 (1978) 1572
114. Michaelson H.B. J. Appl. Phys. 48 (1977) 4729
115. van Hove M.A., and Tong S.Y. Surface Crystallography by LEED: Theory, Computation, and Structural Results (1979), Springer, Berlin
116. Citrin P.H., Wertheim G.K., and Baer Y. Phys. Rev. Lett. 41 (1978) 1425
117. Heister K., Zharnikov M., Grunze M., and Johansson L.S.O. J. Phys. Chem. B 105 (2001) 4058
118. Zharnikov M., and Grunze M. J. Phys.: Condens. Matter 13 (2001) 11333
119. Frey S., Stadler V., Heister K., Eck W., Zharnikov M., Grunze M., Zeysing B., and Terfort A. Langmuir 17 (2001) 2408
120. Hargreaves A., and Rizvi S.H. Acta Crystallogr. 15 (1962) 365
121. Trotter J. Acta Crystallogr. 14 (1961) 1135
122. Almenningen A., Bastiansen O., Fernholt L., Cyvin B.N., Cyvin S.J., and Samdal S. J. Mol. Struct. 128 (1985) 59
123. Bastiansen O. Acta Chem. Scand. 3 (1949) 408
124. Baudour J.L. Acta Crystallogr., Sect. B 47 (1991) 935
125. Karpovich D.S., and Blanchard G.J. Langmuir 10 (1994) 3315
126. Liao S., Shnidman Y., and Ulman A. J. Am. Chem. Soc. 122 (2000) 3688
127. Kondoh H., Kodama C., Sumida H., and Nozoye H. J. Chem. Phys. 111 (1999) 1175
128. Nuzzo R.G., Zegarski B.R., and Dubois L.H. J. Am. Chem. Soc. 109 (1987) 733
129. Lavrich D.J., Wetterer S.M., Bernasek S.L., and Scoles G. J. Phys. Chem. B 102 (1998) 3456
130. Schreiber F., Eberhardt A., Leung T.Y.B., Schwartz P., Wetterer S.M., Lavrich D.J., Berman L., Fenter P., Eisenberger P., and Scoles G. Phys. Rev. B 57 (1998) 12476
131. Wetterer S.M., Lavrich D.J., Cummings T., Bernasek S.L., and Scoles G. J. Phys. Chem. B 102 (1998) 9266
132. Rodriguez J.A., Dvorak J., Jirsak T., Liu G., Hrbek J., Aray Y., and Gonzalez C. J. Am. Chem. Soc. 125 (2003) 276
133. Vericat C., Vela M.E., Andreasen G., Salvarezza R.C., Vazquez L., and Martin-Gago J.A. Langmuir 17 (2001) 4919
134. Mankefors S., Grigoriev A., and Wendin A. Nanotechnology 14 (2003) 849
135. Ishida T., Choi N., Mizutani W., Tokumoto H., Kojima I., Azehara H., Hokari H., Akiba U., and Fujihira M. Langmuir 15 (1999) 6799
136. Zhong C.J., Brush R.C., Anderegg J., and Porter M.D. Langmuir 15 (1999) 518
137. Castner D.G., Hinds K., and Grainger D.W. Langmuir 12 (1996) 5083
138. Felgenhauer T., Rong H.T., and Buck M. J. Electroanal. Chem. 550 (2003) 309
139. Rong H.T., Frey S., Yang Y.J., Zharnikov M., Buck M., Wuhn M., Wöll C., and Helmchen G. Langmuir 17 (2001) 1582
140. Zerbi G., and Sandroni S. Spectrochim. Acta, Part A 24 (1968) 483
141. Bardeen J. Phys. Rev. 71 (1947) 717
142. Tersoff J. Phys. Rev. Lett. 52 (1984) 465
143. Vásquez H., Flores F., Oszwaldowski R., Ortega J., Pérez R., and Kahn A. Appl. Surf. Sci. 234 (2004) 107
144. Vásquez H., Oszwaldowski R., Pou P., Ortega J., Pérez R., Flores F., and Kahn A. Europhys. Lett. 65 (2004) 802
145. Langlais V.J., Schlittler R.R., Tang H., Gourdon A., Joachim C., and Gimzewski J.K. Phys. Rev. Lett. 83 (1999) 2809
146. Piccinin S., Selloni A., Scandolo S., Car R., and Scoles G. J. Chem. Phys. 119 (2003) 6729
147. Levstik A., Filipic C., and Levstik I. J. Phys.: Condens. Matter 2 (1990) 3031
148. Heimel G., Romaner L., Bredas J.L., and Zojer E. Phys. Rev. Lett. 96 (2006) 196806
149. Hasan M., Bethell D., and Brust M. J. Am. Chem. Soc. 124 (2002) 1132
150. De Renzi V., Rousseau R., Marchetto D., Biagi R., Scandolo S., and del Pennino U. Phys. Rev. Lett. 95 (2005) 046804
151. Risko C., Zojer E., Brocorens P., Marder S.R., and Bredas J.L. Chem. Phys. 313 (2005) 151