High charge delocalization and conjugation in oligofuran molecular wires

Chemistry - A European Journal

Volumn 19, Issue 39, 2013, Pages 13140-13150

  Gidron, Ori ^a   Diskin Posner, Yael ^a   Bendikov, Michael ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

charge delocalization; conjugation; oligofurans; oligothiophenes

Indexed keywords

CHARGE DELOCALIZATION; COMPUTATIONAL STUDIES; CONJUGATION; MIXED VALENCE SYSTEMS; OLIGOFURANS; OLIGOTHIOPHENES; ORGANIC ELECTRONICS; SPECTROSCOPIC STUDIES;

AROMATIC COMPOUNDS; ORGANOMETALLICS; SPECTROSCOPIC ANALYSIS;

NANOWIRES;

EID: 84884532815     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301293     Document Type: Article

References (96)

1. M. Wielopolski, D. M. Guldi, T. Clark, N. Martín, Charge and Exciton Transport through Molecular Wires, Wiley-VCH, 2011
2. J. C. Cuevas, E. Scheer, Molecular Electronics: An Introduction to Theory and Experiment, World Scientific, 2010.
3. Handbook of Thiophene-Based Materials (Eds.:, I.F. Perepichka, D.F. Perepichka,), Wiley-VCH, 2009
4. Handbook of Oligo- and Polythiophenes (Ed.:, D. Fichou,), Wiley-VCH, Weinheim, 1999
5. A. Mishra, C.-Q. Ma, P. Bäuerle, Chem. Rev. 2009, 109, 1141-1276
6. I. F. Perepichka, D. F. Perepichka, H. Meng, F. Wudl, Adv. Mater. 2005, 17, 2281-2305
7. P. Bäuerle, J. Becher, J. Lau, P. Mark, in Electronic Materials: The Oligomer Approach, Wiley-VCH, Weinheim, 2007.
8. M. Bendikov, F. Wudl, D. F. Perepichka, Chem. Rev. 2004, 104, 4891-4946
9. J. E. Anthony, Chem. Rev. 2006, 106, 5028-5048.
10. J. Reynolds, T. A. Skotheim, Handbook of Conducting Polymers, 3rd. ed., CRC Press, 2007
11. K. Müllen, G. Wegner, Electronic Materials: The Oligomer Approach, Wiley-VCH, Weinheim, 1998.
12. Y.-J. Cheng, S.-H. Yang, C.-S. Hsu, Chem. Rev. 2009, 109, 5868-5923.
13. N. S. Sariciftci, L. Smilowitz, A. J. Heeger, F. Wudl, Science 1992, 258, 1474-1476
14. H. E. Katz, Z. Bao, J. Phys. Chem. B 2000, 104, 671-678
15. A. Facchetti, Mater. Today 2007, 10, 28-37
16. H. Gilles, in Organic Field-Effect Transistors, CRC Press, 2007, pp. 73-101.
17. D. F. Perepichka, I. F. Perepichka, H. Meng, F. Wudl, in Organic Light-emitting Materials and Devices (Eds.:, Z. Li, H. Meng,), CRC Press, 2006.
18. J. M. Beebe, V. B. Engelkes, L. L. Miller, C. D. Frisbie, J. Am. Chem. Soc. 2002, 124, 11268-11269
19. F. Chen, X. Li, J. Hihath, Z. Huang, N. Tao, J. Am. Chem. Soc. 2006, 128, 15874-15881.
20. G. Peng, M. Strange, K. S. Thygesen, M. Mavrikakis, J. Phys. Chem. C 2009, 113, 20967-20973 and references therein.
21. A. Salomon, D. Cahen, S. Lindsay, J. Tomfohr, V. B. Engelkes, C. D. Frisbie, Adv. Mater. 2003, 15, 1881-1890
22. D. J. Wold, R. Haag, M. A. Rampi, C. D. Frisbie, J. Phys. Chem. B 2002, 106, 2813-2816.
23. L. Venkataraman, J. E. Klare, C. Nuckolls, M. S. Hybertsen, M. L. Steigerwald, Nature 2006, 442, 904-907.
24. B. Q. Xu, X. L. Li, X. Y. Xiao, H. Sakaguchi, N. J. Tao, Nano Lett. 2005, 5, 1491-1495.
25. R. Yamada, H. Kumazawa, T. Noutoshi, S. Tanaka, H. Tada, Nano Lett. 2008, 8, 1237-1240.
26. Y. Miyata, T. Nishinaga, K. Komatsu, J. Org. Chem. 2005, 70, 1147-1153.
27. O. Gidron, Y. Diskin-Posner, M. Bendikov, J. Am. Chem. Soc. 2010, 132, 2148-2150.
28. For recent computational studies, see: S. Sharma, M. Bendikov, Chem. Eur. J. 2013, DOI: 10.1002/chem.201300257.
29. O. Gidron, A. Dadvand, Y. Sheynin, M. Bendikov, D. F. Perepichka, Chem. Commun. 2011, 47, 1976-1978.
30. P. Aguirre-Etcheverry, D. O'Hare, Chem. Rev. 2010, 110, 4839-4864
31. D. M. D'Alessandro, F. R. Keene, Chem. Soc. Rev. 2006, 35, 424-440
32. J.-P. Launay, Chem. Soc. Rev. 2001, 30, 386-397
33. J. Hankache, O. S. Wenger, Chem. Rev. 2011, 111, 5138-5178
34. K. D. Demadis, C. M. Hartshorn, T. J. Meyer, Chem. Rev. 2001, 101, 2655-2686.
35. M.-A. Sato, K. Fukui, M. Sakamoto, S. Kashiwagi, M. Hiroi, Thin Solid Films 2001, 393, 210-216
36. M.-A. Sato, H. Kamine, Chem. Lett. 2009, 38, 924-925
37. M.-A. Sato, M.-A. Sakamoto, S.-I. Kashiwagi, T. Suzuki, M. Hiroi, Bull. Chem. Soc. Jpn. 2001, 74, 1737-1742
38. M.-A. Sato, K. Fukui, Synth. Met. 2007, 157, 619-626
39. K. R. JustinThomas, J. T. Lin, Y. S. Wen, Organometallics 2000, 19, 1008-1012
40. J. M. Speck, R. Claus, A. Hildebrandt, T. Rüffer, E. Erasmus, L. vanAs, J. C. Swarts, H. Lang, Organometallics 2012, 31, 6373-6380.
41. Y. Zhu, M. O. Wolf, J. Am. Chem. Soc. 2000, 122, 10121-10125
42. C.-J. Yao, Y.-W. Zhong, J. Yao, J. Am. Chem. Soc. 2011, 133, 15697-15706.
43. Y. Li, M. Josowicz, L. M. Tolbert, J. Am. Chem. Soc. 2010, 132, 10374-10382.
44. A.-C. Ribou, J.-P. Launay, K. Takahashi, T. Nihira, S. Tarutani, C. W. Spangler, Inorg. Chem. 1994, 33, 1325-1329.
45. A. Boccia, A. G. Marrani, S. Stranges, R. Zanoni, M. Alagia, M. Cossi, M. F. Iozzi, J. Chem. Phys. 2008, 128, 154315.
46. A. Hildebrandt, D. Schaarschmidt, R. Claus, H. Lang, Inorg. Chem. 2011, 50, 10623-10632.
47. A.-C. Ribou, J.-P. Launay, M. L. Sachtleben, H. Li, C. W. Spangler, Inorg. Chem. 1996, 35, 3735-3740.
48. J. Casado, S. RodríguezGonzález, M. C. RuizDelgado, M. MorenoOliva, J. T. LópezNavarrete, R. Caballero, P. delaCruz, F. Langa, Chem. Eur. J. 2009, 15, 2548-2559
49. S. RodríguezGonzález, M. C. RuizDelgado, R. Caballero, P. DelaCruz, F. Langa, J. T. LópezNavarrete, J. Casado, J. Am. Chem. Soc. 2012, 134, 5675-5681.
50. Recently, Wegner etal. have published the synthesis, UV spectra, and a quantitative analysis of oligothiophene-bridged systems capped with a triethylamine group as the redox centers. These organic mixed valence systems are significantly different from the biferrocenyl systems studied here, since the HOMO of the redox centers interacts strongly with the conjugated bridge, resulting in borderline class II-III systems. See, L. G. Reuter, A. G. Bonn, A. C. Stückl, B. He, P. B. Pati, S. S. Zade, O. S. Wenger, J. Phys. Chem. A 2012, 116, 7345-7352.
51. H. Kanato, K. Takimiya, T. Otsubo, Y. Aso, T. Nakamura, Y. Araki, O. Ito, J. Org. Chem. 2004, 69, 7183-7189.
52. A bifuran bridge capped with FeCp(DPPE) was recently prepared using oxidative coupling., K. Johno, Y. Tanaka, T. Koike, M. Akita, Dalton Trans. 2011, 40, 8089-8091.
53. M. Iyoda, T. Kondo, T. Okabe, H. Matsuyama, S. Sasaki, Y. Kuwatani, Chem. Lett. 1997, 35-36.
54. P. Mathur, A. K. Singh, V. K. Singh, P. Singh, Rahul, S. M. Mobin, C. Thöne, Organometallics 2005, 24, 4793-4798.
55. J.-D. Huang, S.-H. Wen, W.-Q. Deng, K.-L. Han, J. Phys. Chem. B 2011, 115, 2140-2147.
56. G. Horowitz, B. Bachet, A. Yassar, P. Lang, F. Demanze, J. L. Fave, F. Garnier, Chem. Mater. 1995, 7, 1337-1341.
57. D. Holmes, S. Kumaraswamy, A. J. Matzger, K. P. C. Vollhardt, Chem. Eur. J. 1999, 5, 3399-3412.
58. D. E. Richardson, H. Taube, Coord. Chem. Rev. 1984, 60, 107-129.
59. J. Sen, H. Taube, Acta Chem. Scand. Ser. A 1979, 33, 125-135
60. N. J. Hill, J. Chem. Soc. Faraday Trans. 2 1972, 68, 427-434.
61. V. Barone, M. Cossi, J. Phys. Chem. A 1998, 102, 1995-2001.
62. U. Salzner, Curr. Org. Chem. 2004, 8, 569-590
63. U. Salzner, A. Aydin, J. Chem. Theory Comput. 2011, 7, 2568-2583
64. N. Kuritz, T. Stein, R. Baer, L. Kronik, J. Chem. Theory Comput. 2011, 7, 2408-2415). Secondly, the model we used lacks a counter ion. Finally, there are deficiencies in the continuous solvent model (CPCM) used in the calculations. We also note that the calculated results for our systems (performed by Prof. U. Salzner, we thank her for sharing these unpublished results with us) are strongly dependent on the amount of HF exchange used, and different amounts of HF exchange lead to different assignments of the transitions with respect to the experimental bands. However, importantly, despite possible deficiencies in the computational levels, our assignment of the IVCT band is backed by the experimental solvent dependence as described in ref. [42]. We note that the experimental systems investigated here are too large to study using high ab initio levels of theory.
65. N. S. Hush, Coord. Chem. Rev. 1985, 64, 135-157
66. N. S. Hush, Prog. Inorg. Chem. 1967, 8, 391-444.
67. In the late 1960s, Robin and Day classified mixed valence systems into three classes, depending on the extent of delocalization. In classII, which is an intermediate between fully localized valences (classI) and completely delocalized valences (classIII), there is some localization of distinct valences, but there is a low activation energy for their interconversion. Some thermal activation is required to induce electron transfer from one site to another via the bridge. See, M. B. Robin, P. Day, Adv. Inorg. Chem. Radiochem. 1968, 10, 247-422 and ref. [19].
68. K. Lancaster, S. A. Odom, S. C. Jones, S. Thayumanavan, S. R. Marder, J.-L. Bredas, V. Coropceanu, S. Barlow, J. Am. Chem. Soc. 2009, 131, 1717-1723.
69. M. Renz, K. Theilacker, C. Lambert, M. Kaupp, J. Am. Chem. Soc. 2009, 131, 16292-16302.
70. A. E. Reed, R. B. Weinstock, F. Weinhold, J. Chem. Phys. 1985, 83, 735-746
71. A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899-926.
72. ab) and the distance decay constant (β), see, O. S. Wenger, Acc. Chem. Res. 2010, 43, 25-35.
73. H. Oevering, M. N. Paddon-Row, M. Heppener, A. M. Oliver, E. Cotsaris, J. W. Verhoeven, N. S. Hush, J. Am. Chem. Soc. 1987, 109, 3258-3269
74. H. B. Gray, J. R. Winkler, Proc. Natl. Acad. Sci. USA 2005, 102, 3534-3539.
75. C. C. Ferrón, M. C. R. Delgado, O. Gidron, S. Sharma, D. Sheberla, Y. Sheynin, M. Bendikov, J. T. L. Navarrete, V. Hernandez, Chem. Commun. 2012, 48, 6732-6734.
76. E. A. Weiss, M. J. Tauber, R. F. Kelley, M. J. Ahrens, M. A. Ratner, M. R. Wasielewski, J. Am. Chem. Soc. 2005, 127, 11842-11850
77. R. H. Goldsmith, L. E. Sinks, R. F. Kelley, L. J. Betzen, W. Liu, E. A. Weiss, M. A. Ratner, M. R. Wasielewski, Proc. Natl. Acad. Sci. USA 2005, 102, 3540-3545
78. W. B. Davis, W. A. Svec, M. A. Ratner, M. R. Wasielewski, Nature 1998, 396, 554.
79. We note that an extremely low β values of 0.01 A-1 measured for oligo p-phenylene vinylene was reported:, F. Giacalone, J. L. Segura, N. Martín, D. M. Guldi, J. Am. Chem. Soc. 2004, 126, 5340-5341.
80. ab)), However, even after multiplication, the β values reported here are at the lower end of the scale. See, C.-P. Hsu, Acc. Chem. Res. 2009, 42, 509-518.
81. S. Creager, C. J. Yu, C. Bamdad, S. O'Connor, T. MacLean, E. Lam, Y. Chong, G. T. Olsen, J. Luo, M. Gozin, J. F. Kayyem, J. Am. Chem. Soc. 1999, 121, 1059-1064
82. S. B. Sachs, S. P. Dudek, R. P. Hsung, L. R. Sita, J. F. Smalley, M. D. Newton, S. W. Feldberg, C. E. D. Chidsey, J. Am. Chem. Soc. 1997, 119, 10563-10564
83. R. E. Holmlin, R. Haag, M. L. Chabinyc, R. F. Ismagilov, A. E. Cohen, A. Terfort, M. A. Rampi, G. M. Whitesides, J. Am. Chem. Soc. 2001, 123, 5075-5085.
84. Conjugation and charge delocalization were also previously studied in oligoynes, but their electronic coupling was found to be significantly lower than that of oligoenes. See, C. Levanda, K. Bechgaard, D. O. Cowan, J. Org. Chem. 1976, 41, 2700-2704.
85. For similar twisting studies of oligofurans see ref. [15] and, F. Liu, P. Zuo, L. Meng, S. Zheng, J. Mol. Struct. 2005, 726, 189-196.
86. J. A. Joule, Heterocyclic Chemistry, 4 th ed., Blackwell Publishing, 2000, Chapter 15
87. M. K. Cyrañski, T. M. Krygowski, A. R. Katritzky, P. v. R. Schleyer, J. Org. Chem. 2002, 67, 1333-1338
88. A. Stanger, J. Org. Chem. 2006, 71, 883-893.
89. D. L. Reger, T. D. Wright, C. A. Little, J. J. S. Lamba, M. D. Smith, Inorg. Chem. 2001, 40, 3810-3814.
90. Gaussian09, RevisionA.02, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian, Inc. Wallingford CT, 2009.
91. R.G. Parr, W. Yang, Density-functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989
92. W. Koch, M. C. Holthausen, A Chemist's Guide to Density Functional Theory, Wiley-VCH, New York, 2000.
93. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789
94. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
95. R. E. Stratmann, G. E. Scuseria, M. J. Frisch, J. Chem. Phys. 1998, 109, 8218-8224.
96. S. S. Zade, M. Bendikov, Chem. Eur. J. 2007, 13, 3688-3700.