Molecular wires comprising π-extended ethynyl- and butadiynyl-2,5- diphenyl-1,3,4-oxadiazole derivatives: Synthesis, redox, structural, and optoelectronic properties

Journal of the American Chemical Society

Volumn 128, Issue 11, 2006, Pages 3789-3799

  Wang, Changsheng ^a   Pålsson, Lars Olof ^a   Batsanov, Andrei S ^a   Bryce, Martin R ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BUTADIENE; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; CYCLIC VOLTAMMETRY; SYNTHESIS (CHEMICAL); X RAYS;

AROMATIC MOIETIES; BUTADIYNYLENE DERIVATIVES; CONJUGATED MOLECULES; ELECTRON-WITHDRAWING EFFECTS;

MOLECULAR STRUCTURE;

2 METHYL 3,5 HEXADIYN 2 OL; 9 (4,5 DIMETHYL 1,3 DITHIOL 2 YLIDINE)FLUORENE; ALCOHOL; FLUORENE DERIVATIVE; OXADIAZOLE DERIVATIVE; TETRATHIAFULVALENE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONJUGATION; CRYSTAL; CYCLIC POTENTIOMETRY; FLAME PHOTOMETRY; FLUORESCENCE; OXIDATION; OXIDATION REDUCTION POTENTIAL; SHELF LIFE; SONOGASHIRA REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 33645386777     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0577600     Document Type: Article

References (80)

1. (a) Sonogashira, K. In Comprehensive Organic Synthesis; Trost B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; vol. 3, p 521.
2. (b) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weiheim; 1998; p 203.
3. (c) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46.
4. (a) Bunz, U. H. F. Chem. Rev. 2000, 100, 1065.
5. (b) Tour, J. M. Acc. Chem. Res. 2000, 33, 791.
6. (c) Robertson, N.; McGowan, C. A. Chem. Soc. Rev. 2003, 32, 96.
7. (a) Redmore, N. P.; Rubstov, I. V.; Therien, M. J. J. Am. Chem. Soc. 2003, 125, 8769.
8. (b) Screen, T. O.; Thorne, J. R. G.; Denning, R. G.; Bucknall, D. G.; Anderson, H. L. J. Mater. Chem. 2003, 13, 2796.
9. (a) Nielsen, M. B.; Moonen, N. N. P.; Boudon, C.; Gisselbrecht, J.-P.; Seiler, P.; Gross, M.; Diederich, F. Chem. Commun. 2001, 1848.
10. (b) Nielsen, M. B.; Utesch, N. F.; Moonen, N. N. P.; Boudon, C.; Gisselbrecht, J.-P.; Concilio, S.; Piotto, S. P.; Seiler, P.; Günter, P.; Gross, M.; Diederich, F. Chem.-Eur. J. 2002, 8, 3601.
11. (a) Dembinski, R.; Bartik, T.; Bartik, B.; Jaegerr, M.; Gladysz, J. A. J. Am. Chem. Soc. 2000, 122, 810.
12. (b) Benniston, A. C.; Harriman, A.; Li, P.; Sams, C. A. J. Am. Chem. Soc. 2005, 127, 2553.
13. Mohr, W.; Stahl, J.; Hampel, F.; Gladysz, J. A. Chem.-Eur. J. 2003, 9, 3324.
14. (a) Eisler, S.; Chahal, N.; McDonald, R.; Tykwinski, R. R. Chem.-Eur. J. 2003, 9, 2542.
15. (b) Eisler, S.; Slepkov, A. D.; Elliott, E.; Luu, T.; McDonald, R.; Hegmann, F. A.; Tykwinski, R. R. J. Am. Chem. Soc. 2005, 127, 2666.
16. (a) Karzazi, Y.; Cornil, J.; Brédas, J. L. Nanotechnology 2003, 14, 165.
17. (b) Tour, J. M.; Cheng, L.; Nackashi, D. P.; Yao, Y.; Flatt, A. K.; St. Angelo, S. K.; Mallouk, T. E.; Franzon, P. D. J. Am. Chem. Soc. 2003, 125, 13279.
18. (c) Cornil, J.; Karzazi, Y.; Brédas, J. L. J. Am. Chem. Soc. 2002, 124, 3516.
19. (d) Seminario, J. M.; Derosa, P. A.; Bastos, J. L. J. Am. Chem. Soc. 2002, 124, 10266.
20. (a) Biswas, M.; Nguyen, P.; Marder, T. B.; Khundkar, L. R. J. Phys. Chem. A 1997, 101, 1698.
21. (b) Rogers, D. W.; Matsunaga, N.; Zavitsas, A. A.; McLafferty, F. J.; Liebman, J. F. Org. Lett. 2003, 5, 2373.
22. (c) Rogers, D. W.; Matsunaga, N.; McLafferty, F. J.; Zavitsas, A. A.; Liebman, J. F. J. Org. Chem. 2004, 69, 7143.
23. (d) Jarowski, P. D.; Wodrich, M. D.; Wannere, C. S.; Schleyer, P. v. R.; Houk, K. N. J. Am. Chem. Soc. 2004, 126, 15036.
24. Schulz, B.; Bruma, M.; Brehmer, L. Adv. Mater. 1997, 9, 601.
25. Reviews; (a) Kraft, A. Liebigs Ann./Recueil. 1997, 1463.
26. (b) Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem., Int. Ed. 1998, 37, 402.
27. (c) Mitschke U.; Bäuerle, P. J. Mater. Chem. 2000, 10, 1471.
28. (d) Hughes, G.; Bryce, M. R. J. Mater. Chem. 2005, 15, 94.
29. (a) Adachi, C.; Tokito, S.; Tsutsui, T.; Saito, S. Jpn. J. Appl. Phys. 1988, 27, L713.
30. (b) Wang, C.; Jung, G.-Y.; Batsanov, A. S.; Bryce, M. R.; Petty, M. C. J. Mater. Chem. 2002, 12, 173.
31. (c) Chien, Y.-Y.; Wong, K.-T.; Chou, P.-T.; Cheng, Y.-M. Chem. Commun. 2002, 2874.
32. Cha, S. W.; Choi, S.-H.; Kim, K.; Jin, J.-I. J. Mater. Chem. 2003, 13, 1900.
33. (a) Peng, Z.; Bao, Z.; Galvin, M. E. Chem. Mater. 1998, 10, 2086.
34. (b) Chen, Z.-K.; Meng, H.; Lai, Y.-H.; Huang, W. Macromolecules 1999, 32, 4351.
35. (c) Wang, C.; Kilitziraki, M.; Palsson, L.-O.; Bryce, M. R.; Monkman, A. P.; Samuel, I. D. W. Adv. Funct. Mater. 2001, 11, 47.
36. (d) Shu, C.-F.; Dodda, R.; Wu, F.-I.; Liu, M. S.; Jen, A. K.-Y. Macromolecules 2003, 36, 6698.
37. Wang, C.; Butsanov. A. S.; Bryce, M. R. Chem. Commun. 2004, 578.
38. For reviews of TTF chemistry see: (a) Segura, J. L.; Martín, N. Angew. Chem., Int. Ed. 2001, 40, 1372.
39. (b) Bryce, M. R. J. Mater. Chem. 2000, 10, 589.
40. (c) Nielsen, M. B.; Lomholt, C.; Becher, J. Chem. Soc. Rev. 2000, 29, 153.
41. (a) Havens, S. H.; Hergenrother, P. M. J. Org. Chem. 1985, 50, 1763.
42. (b)MacBride, J. A. H.; Wade, K. Synth. Commun. 1996, 26, 2039.
43. Ames, D. E.; Bull, D.; Takunda, C. Synthesis 1981, 364.
44. Gusev, I.; Kucherov, V. F. Bull. Acad. Sci. UUSR Div. Chem. Sci. (Engl. Transl.) 1962, 995.
45. Unsymmetrically substituted 1,3-buladiynes have been efficiently synthesized via Pd-catalyzed cross-coupling of 1,3-diynylzines (Negishi, E.; Hata, M.; Xu, C. Org. Lett. 2000, 2, 3687)
46. or via alkylidine carbenoid rearrangements (Shi Shun, A. L. K.; Chernick, E. T.; Eisler, S.; Tykwinski, R. R. J. Org. Chem. 2003, 68, 1339).
47. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
48. Chow, H.-F.; Wan, C.-W.; Low, K.-H.; Yeung, Y.-Y. J. Org. Chem. 2001, 66, 1910.
49. A self-coupling method has been developed on the basis of Sonogashira conditions without using aromatic halides. (Batsanov, A. S.; Collings, J. C.; Fairlamb, I. J. S.; Holland, J. P.; Howard, J. A. K.; Lin, Z.; Marder, T. B.; Parsons, A. C.; Ward, R. M.; Zhu, J. J. Org. Chem. 2005, 70, 703.)
50. -1) indicated that 4a had the smallest net charge (-0.148) on the terminal sp carbon atom, compared with those of 4-fluorophenylacetylene (-0.157). TMSA (-0.198), and 4-(phenylethynyl) phenylacetylene (-0.163): i.e., 4a was the most acidic of these four compounds.
51. We make this comparison because the less acidic TMSA (Lewis, J.; Raithby, P. R.; Wong, W.-Y. J. Organomet. Chem. 1998, 556, 219), 4- fluorophenylacetylene, and 4-(phenylethynyl)phenylacetylene have been cross-coupled with 2,7-dibromofluorenone under similar conditions,
52. (Ipaktschi, J.; Hosseinzadeh, R.; Schlaf, P.; Eckert, T. Helv. Chim. Acta 2000, 83, 1224). In addition, the acetylides of 4 and the diacetylides of 8 were less reactive to nucleophilic reactions with ketones and aldehydes than were standard alkyl and aryl acetylenes, which may also be because of the higher acidity of these OXD acetylenes (hence lower nucleophilicity of their derived acetylides).
53. (Kreher, D.; Batsanov, A. S.; Wang, C.; Bryce, M. R. Org. Biomol. Chem. 2004, 2, 858). Self-coupling of 8a, in the absence of an aromatic halide, gave the tetrayne analogue of 9 in 40% yield: details will be published separately.
54. John, D. E.; Moore, A. J.; Bryce, M. R.; Batsanov, A. S.; Howard, J. A. K. Synthesis 1998, 826.
55. Allen, F. H.; Taylor, R. Chem. Soc. Rev. 2004, 33, 463.
56. (a) Inoue, K.; Koga, N.; Iwamua, H. J. Am. Chem. Soc. 1991, 113, 9803.
57. (b) Inoue, K.; Iwamua, H. Adv. Mater. 1992, 4, 801.
58. (c) Classen, J.; Gleiter, R.; Rominger, F. Eur. J. Inorg. Chem. 2002, 2040.
59. (a) Keller, M. B.; Rzepa, H. S.; White, A. J. P.; Williams, D. J. First Electron. Conf. Trends in Org. Chem. 1995; p 50 (cit. from CSD, refcode NAMLAO).
60. (b) Murty, K. V. S. N.; Vasella, A. Helv. Chim. Acta 2001, 84, 939.
61. (c) Xi, O.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 2003, 125, 12400.
62. (a) Baughmann, R. H. J. Appl. Phys. 1972, 43, 4362.
63. (b) Enkelmann, V. Chem. Mater. 1994, 6, 1337.
64. (c) Coates, O. W.; Dunn, A. R.; Henling, L. M.; Dougherty, D. A.; Grubbs, R. H. Angew. Chem., Int. Ed. 1997, 36, 248.
65. Tykwinski, R. R.; Zhao, Y. M. Synlett 2002, 1939.
66. Schiemenz, G. P.; Nielsen, P. Phosphorus Sulfur 1984, 21, 259.
67. Mangini, P. J. Chem. Soc. 1956, 4954.
68. Graham, E. M.; Miskowski, V. M.; Perry, J. W.; Coulter, D. R.; Stiegman, A. E.; Schaefer, W. P.; Marsh, R. E. J. Am. Chem. Soc. 1989, 111, 8771.
69. (a) Williams, D. H.; Fleming, I. Spectroscopic Methods in Organic Chemistry, 4th ed.; McGraw-Hill Book Company: London, 1989; p 20.
70. (b) Roncali, J. Chem. Rev. 1997, 97, 173.
71. (c) Perepichka, D. F.; Bryce, M. R. Angew. Chem., Int. Ed. 2005, 44, 5370.
72. Moore, A. J.; Bryce, M. R.; Batsanov, A. S.; Cole, J. C.; Howard, J. A. K. Synthesis 1995, 274.
73. Sotzing, G. A.; Reynolds, J. R.; Steel, P. J. Adv. Mater. 1997, 9, 795.
74. Apperloo, J. J.; Groenendaal, L.; Verheyen, H.; Jayakannan, M.; Janssen, R. A. J.; Dkhissi, A.; Beljonne, D.; Lazzaroni, R.; Bredas, J.-L. Chem.-Eur. J. 2002, 8, 2384.
75. (a) Perepichka, I. F.; Kuz'mina, L. G.; Perepichka, D. F.; Bryce, M. R.; Goldenberg, L. M.; Popov, A. F.; Howard, J. A. K. J. Org. Chem. 1998, 63, 6484.
76. (b) Perepichka, I. F.; Popov, A. F.; Orekhova, T. V.; Bryce, M. R.; Andrievskii, A. M.; Batsanov, A. S.; Howard, J. A. K.; Sukolov, N. I. J. Org. Chem. 2000, 65, 3053.
77. (a) Wang, C.; Bryce, M. R.; Batsanov, A. S.; Stanley, C. F.; Beeby, A.; Howard, J. A. K. J. Chem. Soc., Perkin Trans. 2 1997, 1671.
78. (b) Farren, C.; Christensen, C. A.; FitzGerald, S.; Bryce, M. R.; Beeby, A. J. Org. Chem. 2002, 67, 9130.
79. (c) Luosli, C.; Jia, C.; Liu, S.-X.; Haas, M.; Dias, M.; Levillain, E.; Neels, A.; Labat, G.; Hauser, A.; Decartins, S. J. Org. Chem. 2005, 70, 4988.
80. Zimmer, K.; Gödicke, B.; Hoppmeier, M.; Meyer, H.; Schweig, A. Chem. Phys., 1999, 248, 263.