Electronic communication and negative binding cooperativity in diborylated bithiophenes

Journal of the American Chemical Society

Volumn 128, Issue 51, 2006, Pages 16554-16565

  Sundararaman, Anand ^a   Venkatasubbaiah, Krishnan ^a   Victor, Maria ^a   Zakharov, Lev N ^b,c   Rheingold, Arnold L ^b   Jäkle, Frieder ^a  

^a RUTGERS UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF OREGON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIBORYLATED BITHIOPHENES; ELECTRONIC COMMUNICATION; UV VISIBLE ABSORPTION; UV VISIBLE ABSORPTION SPECTROSCOPY;

BINDING ENERGY; BORON COMPOUNDS; CHEMICAL BONDS; PROBABILITY DENSITY FUNCTION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

OLEFINS;

2,2' DITHIOPHENE; BIOTHIOPHENE DERIVATIVE; BORANE DERIVATIVE; BORON; PYRIDINE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CHEMICAL BINDING; CONJUGATION; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; DENSITY FUNCTIONAL THEORY; ELECTROCHEMISTRY; ELECTRONICS; FLAME PHOTOMETRY; FLUOROMETRY; LUMINESCENCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; TITRIMETRY; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

BINDING SITES; BORON COMPOUNDS; ELECTROCHEMISTRY; ELECTRONS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; PYRIDINES; QUANTUM THEORY; SENSITIVITY AND SPECIFICITY; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; THIOPHENES;

EID: 33845925301     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja064396b     Document Type: Article

References (124)

1. (a) Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds. Handbook of Conducting Polymers, 2nd ed.; Marcel Dekker, Inc.: New York, 1997.
2. (b) Fichou, D., Ed. Handbook of Oligo- and Polythiophenes; Wiley-VCH: Weinheim, 1999.
3. (c) Hadziioannou, G., van Hutten, P. F., Eds. Semiconducting Polymers; Wiley-VCH: Weinheim, 2000.
4. (d) Nalwa, H. S., Ed. Handbook of Advanced Electronic and Photonic Materials and Devices, Volume 8: Conducting Polymers; Academic Press: San Diego, 2001.
5. (e) Wallace, G. G.; Spinks, G. M.; Kane-Maguire, L. A. P. Conductive Electroactive Polymers: intelligent Materials Systems, 2nd ed.; CRC Press: Boca Raton, FL, 2002.
6. (f) Friend, R. H. Pure Appl. Chem. 2001, 73, 425-430.
7. (g) Pron, A.; Rannou, P. Progr. Polym. Sci. 2002, 27, 135-190.
8. (a) Abd-El-Aziz, A. S.; Carraher, C. E., Jr.; Pittman, C. U., Jr.; Sheats, J. E.; Zeldin, M. Macromolecules Containing Metal and Metal-Like Elements, Volume I, A Half-Century of Metal- and Metalloid-Containing Polymers; John Wiley & Sons: Hoboken, NJ, 2003.
9. (b) Manners, I. Synthetic Metal-Containing Polymers; Wiley-VCH: Weinheim, 2004.
10. (c) Chandrasekhar, V. Inorganic and Organometallic Polymers; Springer-Verlag; New York, 2005.
11. (d) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; Wiley-VCH: New York, 2000.
12. (e) Hockemeyer, J.; Castel, A.; Riviere, P.; Satge, J.; Ryder, K. G.; Drury, A.; Davey, A. P.; Blau, W. J. Appl. Organomet. Chem. 1997, 11, 513-521.
13. (f) Pickup, P. G. J. Mater. Chem. 1999, 9, 1641-1653.
14. (g) Matsumi, N.; Chujo, Y. Spec. Publ. R. Soc. Chem. 2000, 253, 51-58.
15. (h) Yamaguchi, S.; Tamao, K. Silicon-Containing Polym. 2000, 461-498.
16. (i) Wolf, M. O. Adv. Mater. 2001, 13, 545-553.
17. (j) Puddephatt, R. J. Coord. Chem. Rev. 2001, 216-217, 313-332.
18. (k) Nishihara, H. Adv. Inorg. Chem. 2002, 53, 41-86.
19. (l) Yamaguchi, S.; Tamao, K. J. Organomet. Chem. 2002, 653, 223-228.
20. (m) Hissler, M.; Dyer, P. W.; Reau, R. Coord. Chem. Rev. 2003, 244, 1-44.
21. (n) Moorlag, C.; Sih, B. C.; Stott, T. L.; Wolf, M. O. J. Mater. Chem. 2005, 15, 2433-2436.
22. (o) Jäkle, F. Coord. Chem. Rev. 2006, 250, 1107-1121.
23. For reviews, see: (a) Entwistle, C. D.; Murder, T. B. Angew. Chem., Int. Ed. 2002, 41, 2927-2931.
24. (b) Entwistle, C. D.; Marder, T. B. Chem. Mater. 2004, 16, 4574-4585.
25. (c) Jäkle, F. Boron: Organoboranes. In Encyclopedia of Inorganic Chemistry, 2nd ed.; King, R. B., Ed.; Wiley: Chichester, 2005.
26. (d) Yamaguchi, S.; Wakamiya, A. Pure Appl. Chem. 2006, 78, 1413-1424.
27. Recent examples: (e) Lee, B. Y.; Wang, S.; Putzer, M.; Bartholomew, G. P.; Bu, X.; Bazan, G. C. J. Am. Chem. Soc. 2000, 122, 3969-3970.
28. (f) Liu, Z.-Q.; Fang, Q.; Wang, D.; Xue, G.; Yu, W.-T.; Shao, Z.-S.; Jiang, M.-H. Chem. Commun. 2002, 2900-2901.
29. (g) Liu, Z.-Q.; Fang, Q.; Cao, D.-X.; Wang, D.; Xu, G.-B. Org. Lett. 2004, 6, 2933-2936.
30. (h) Jia, W.-L.; Bai, D.-R.; McCormick, T.; Liu, Q.-D.; Motala, M.; Wang, R.-Y.; Seward, C.; Tao, Y.; Warm, S. Chem.-Eur. J. 2004, 10, 994-1006.
31. (i) Kim, S.; Song, K.-H.; Kang, S. O.; Ko, J. Chem. Commun. 2004, 68-69.
32. (j) Jia, W. L.; Feng, X. D.; Bai, D. R.; Lu, Z. H.; Wang, S.; Vamvounis, G. Chem. Mater. 2005, 17, 164-170.
33. (k) Cao, H.; Ma, J.; Zhang, G.; Jiang, Y. Macromolecules 2005, 38, 1123-1130.
34. (l) Ulrich, G.; Goze, C.; Guardigli, M.; Roda, A.; Ziessel, R. Angew. Chem., Int. Ed. 2005, 44, 3694-3698.
35. (m) Charlot, M.; Porrès, L.; Entwistle, C. D.; Beeby, A.; Marder, T. B.; Blanchard-Desce, M. Phys. Chem. Chem. Phys. 2005, 7, 600-606.
36. (n) Agou, T.; Kobayashi, J.; Kawashima, T. Org. Lett. 2005, 7, 4373-4376.
37. (o) Zhang, H.; Huo, C.; Zhang, J.; Zhang, P.; Tian, W.; Wang, Y. Chem. Commun. 2006, 281-283.
38. (p) Yuan, Z.; Entwistle, C. D.; Collings, J. C.; Albesa-Jové, D.; Batsanov, A. S.; Howard, J. A. K.; Kaiser, H. M.; Kaufmann, D. E.; Poon, S.-Y.; Wong, W.-Y.; Jardin, C.; Fathallah, S.; Boucekkine, A.; Halet, J.-F.; Taylor, N. J.; Marder, T. B. Chem.-Eur. J. 2006, 12, 2758-2771.
39. (q) Stahl, R.; Lambert, C.; Kaiser, C.; Wortmann, R.; Jakober, R. Chem.-Eur. J. 2006, 12, 2358-2370. See also citations in ref 5.
40. For recent examples of tricoordinate organoboron polymers, see: (a) Matsumi, N.; Naka, K.; Chujo, Y. J. Am. Chem. Soc. 1998, 120, 5112-5113.
41. (b) Matsumi, N.; Naka, K.; Chujo, Y. J. Am. Chem. Soc. 1998, 120, 10776-10777.
42. (c) Matsumoto, F.; Matsumi, N.; Chujo, Y. Polym. Bull. 2001, 46, 257-262.
43. (d) Kobayashi, H.; Sato, N.; Ichikawa, Y.; Miyata, M.; Chujo, Y.; Matsuyama, T. Synth. Met. 2003, 135-136, 393-394.
44. (e) Corriu, R. J.-P.; Deforth, T.; Douglas, W. E.; Guerrero, G.; Siebert, W. S. Chem. Commun. 1998, 963-964.
45. (f) Heilmann, J. B.; Scheibitz, M.; Qin, Y.; Sundararaman, A.; Jäkle, F.; Kretz, T.; Bolte, M.; Lerner, H.-W.; Holthausen, M. C.; Wagner, M. Angew. Chem., Int. Ed. 2006, 45, 920-925. See also citations in ref 6.
46. (a) Yamaguchi, S.; Shirasaka, T.; Tamao, K. Org. Lett. 2000, 2, 4129-4132.
47. (b) Yamaguchi, S.; Akiyama, S.; Tamao, K. J. Am. Chem. Soc. 2000, 122, 6335-6336.
48. (c) Yamaguchi, S.; Akiyama, S.; Tamao, K. J. Am. Chem. Soc. 2001, 123, 11372-11375.
49. (d) Yamaguchi, S.; Shirasaka, T.; Akiyama, S.; Tamao, K. J. Am. Chem. Soc. 2002, 124, 8816-8817.
50. (e) Yamaguchi, S.; Akiyama, S.; Tamao, K. J. Organomet. Chem. 2002, 652, 3-9.
51. (f) Cooper, C. R.; Spencer, N.; James, T. D. Chem. Commun. 1998, 1365-1366.
52. (g) Jia, W.-L.; Song, D.; Wang, S. J. Org. Chem. 2003, 68, 701-705.
53. (h) Kubo, Y.; Yamamoto, M.; Ikeda, M.; Takeuchi, M.; Shinkai, S.; Yamaguchi, S.; Tamao, K. Angew. Chem., Int. Ed. 2003, 42, 2036-2040.
54. (i) Sole, S.; Gabbaï, F. P. Chem. Commun. 2004, 1284-1285.
55. (j) Melaimi, M.; Gabbaï. F. P. J. Am. Chem. Soc. 2005, 127, 9680-9681.
56. (k) Zhao, J.; James, T. D. J. Mater. Chem. 2005, 15, 2896-2901.
57. (l) Zhao, J.; James, T. D. Chem. Commun. 2005, 1889-1891.
58. (m) Zhu, L.; Zhong, Z.; Anslyn, E. V. J. Am. Chem. Soc. 2005, 127, 4260-4269.
59. (n) Koskela, S. J. M.; Fyles, T. M.; James, T. D. Chem. Commun. 2005, 945-947.
60. (o) Kubo, Y.; Ishida, T.; Kobayashi, A.; James, T. D. J. Mater. Chem. 2005, 15, 2889-2895.
61. (p) Bresner, C.; Aldridge, S.; Fallis, I. A.; Jones, C.; Ooi, L.-L. Angew. Chem., Int. Ed. 2005, 44, 3606-3609.
62. (q) Liu, Z.-Q.; Shi, M.; Li, F.-Y.; Fang, Q.; Chen, Z.-H.; Yi, T.; Huang, C.-H. Org. Lett. 2005, 7, 5481-5484.
63. (r) Neumann, T.; Dienes, Y.; Baumgartner, T. Org. Lett. 2006, 8, 495-497.
64. (s) Liu, X. Y.; Bai, D. R.; Wang, S. Angew. Chem., Int. Ed. 2006, 45, 5475-5478.
65. (t) Hudnall, T. W.; Melaimi, M.; Gabbaï, F. P. Org. Lett. 2006, 8, 2747-2749.
66. (u) Melaimi, M.; Solé, S.; Chiu, C.-W.; Wang, H.; Gabbaï. F. P. Inorg. Chem. 2006, 45, 8136-8143.
67. (v) Thanthiriwatte, K. S.; Gwaltney, S. R. J. Phys. Chem. A 2006, 110, 2434-2439.
68. Polymeric organoboron sensor Systems: (a) Miyata, M.; Chujo, Y. Polym. J. 2002, 34, 967-969.
69. (b) Sundararaman, A.; Victor, M.; Varughese, R.; Jäkle, F. J. Am. Chem. Soc. 2005, 127, 13748-13749.
70. (c) Parab, K.; Venkatasubbaiah, K.; Jäkle, F. J. Am. Chem. Soc. 2006, 128, 12879-12885.
71. See ref 6b.
72. McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2537-2574.
73. (a) Kaim, W.; Schulz, A. Angew. Chem., Int. Ed. Engl. 1984, 23, 615-616.
74. (b) Schulz, A.; Kaim, W. Chem. Ber. 1989, 122, 1863-1868.
75. (c) Lichtblau, A.; Kaim, W.; Schulz, A.; Stahl, T. J. Chem. Soc., Perkin Trans. 2 1992, 1497-1501.
76. (d) Lichtblau, A.; Hausen, H.-D.; Schwarz, W.; Kaim, W. Inorg. Chem. 1993, 32, 73-78.
77. (e) Fiedler, J.; Zalis, S.; Klein, A.; Hornung, F. M.; Kaim, W. Inorg. Chem. 1996, 35, 3039-3043.
78. These and related diborylated oligothiophene derivatives have been shown to act as efficient electron transport materials in organic light emitting devices (OLEDs); see: (a) Noda, T.; Shirota, Y. J. Am. Chem. Soc. 1998, 120, 9714-9715.
79. (b) Noda, T.; Ogawa, H.; Shirota, Y. Adv. Mater. 1999, 11, 283-285.
80. (c) Shirota, Y.; Kinoshita, M.; Noda, T.; Okumoto, K.; Ohara, T. J. Am. Chem. Soc. 2000, 122, 11021-11022.
81. (d) Okumoto, K.; Ohara, T.; Noda, T.; Shirota, Y. Synth. Met. 2001, 121, 1655-1656.
82. (e) Kinoshita, M.; Kita, H.; Shirota, Y. Adv. Funct. Mater. 2002, 12, 780-786.
83. (f) Mazzeo, M.; Vitale, V.; Sala, F. D.; Anni, M.; Barbarella, G.; Favaretto, L.; Sotgiu, G.; Cingolani, R.; Gigli, G. Adv. Mater. 2005, 17, 34-39.
84. (a) Müller, P.; Huck, S.; Koppel, H.; Pritzkow, H.; Siebert, W. Z. Naturforsch., B: Chem. Sci. 1995, 50, 1476-1484.
85. (b) Wang, H.; Gabbai, F. P. Organometallics 2005, 24, 2898-2902.
86. (c) Venkatasubbaiah, K.; Zakharov, L. N.; Kassel, W. S.; Rheingold, A. L.; Jäkle, F. Angew. Chem., Int. Ed. 2005, 44, 5428-5433.
87. For cooperative effect in the binding of neutral nucleophiles to a bidentate Lewis acid, see: Chase, P. A.; Henderson, L. D.; Piers, W. E.; Parvez, M.; Clegg, W.; Elsegood, M. R. J. Organometallics 2006, 25, 349-357.
88. For the use of arylcopper species as aryl transfer reagents, see: Sundararaman, A.; Jäkle, F. J. Organomet. Chem. 2003, 681, 134-142.
89. (a) Eisch, J. J.; Kotowicz, B. W. Eur. J. Inorg. Chem. 1998, 761-769.
90. (b) Cheng, X.; Slebodnick, C.; Deck, P. A.; Billodeaux, D. R.; Fronczek, F. R. Inorg. Chem. 2000, 39, 4921-4926.
91. (c) Gamboa, J. A.; Sundararaman, A.; Kakalis, L.; Lough, A. J.; Jäkle, F. Organometallics 2002, 21, 4169-4181.
92. (d) Boshra, R.; Sundararaman, A.; Zakharov, L. N.; Incarvito, C. D.; Rheingold, A. L.; Jäkle, F. Chem.-Eur. J. 2005, 11, 2810-2824.
93. Piers, W. E. Adv. Organomet. Chem. 2005, 52, 1-76.
94. (a) Blount, J. F.; Finocchiaro, P.; Gust, D.; Mislow, K. J. Am. Chem. Soc. 1973, 95, 7019-7029.
95. (b) Toyota, S.; Asakura, M.; Oki, M.; Toda, F. Bull. Chem. Soc. Jpn. 2000, 73, 2357-2362.
96. (c) See ref 3p.
97. A Cambridge Structure Database search gave a mean C-C distance of 1.449 Å for other bithiophene derivatives.
98. Alternating stacks of electron-deficient fluorinated arenes with arenes are more common: for example, see: (a) Williams, J. H. Acc. Chem. Res. 1993, 26, 593-598.
99. (b) Pratt Brock, C.; Naae, D. G.; Goodhand, N.; Hamor, T. A. Acta Crystallogr. 1978, B34, 3691-3696.
100. (c) Coates, G. W.; Dunn, A. R.; Henling, L. M.; Dougherty, D. A.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 248-251.
101. (d) Bartholomew, G. P.; Bu, X.; Bazan, G. C. Chem. Mater. 2000, 12, 2311-2318.
102. (e) Collings, J. C.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B. Acta Crystallogr. 2001, C57, 870-872.
103. (f) Collings, J. C.; Roscoe, K. P.; Thomas, R. L.; Batsanov, A. S.; Stimson, L. M.; Howard, J. A. K.; Marder, T. B. New J. Chem. 2001, 25, 1410-1417.
104. (g) Collings, J. C.; Roscoe, K. P.; Robins, E. G.; Batsanov, A. S.; Stimson, L. M.; Howard, J. A. K.; Clark, S. J.; Marder, T. B. New J. Chem. 2002, 26, 1740-1746.
105. 2, see: Yuan, Z.; Taylor, N. J.; Ramachandran, R.; Marder, T. B. Appl. Organomet. Chem. 1996, 10, 305-316.
106. Carpenter, B. E.; Piers, W. E.; Parvez, M.; Yap, G. P. A.; Rettig, S. J. Can. J. Chem. 2001, 79, 857-867.
107. For a detailed account on stacking effects in a related diborylated dithienothiophene derivative, see ref 10f.
108. 2 (input file from X-ray data). The orbital representations were generated using Gaussview.
109. Scheibitz, M.; Bolte, M.; Bats, J. W.; Lerner, H.-W.; Nowik, I.; Herber, R. H.; Krapp, A.; Lein, M.; Holthausen, M. C.; Wagner, M. Chem. Eur. J. 2005, 11, 584-603.
110. 2 as the supporting electrolyte: Thomas, K. R. J.; Lin, J. T.; Wen, Y. S. Organometallics 2000, 19, 1008-1012.
111. See also: Scheibitz, M.; Heilmann, J. B.; Winter, R. F.; Bolte, M.; Bats, J. W.; Wagner, M. Dalton Trans. 2005, 159-170.
112. Connors, K. A. Binding Constants; Wiley-Interscience: London, 1987.
113. Brown, H. C.; Barbaras, G. K. J. Am. Chem. Soc. 1947, 69, 1137-1144.
114. (a) Cairncross, A.; Sheppard, W. A.; Wonchoba, E. Org. Synth. 1980, 59, 122-131.
115. (b) Sundararaman, A.; Lalancette, R. A.; Zakharov, L. N.; Rheingold, A. L.; Jäkle, F. Organometallics 2003, 22, 3526-3532.
116. Guillaneux, D.; Kagan, H. B. J. Org. Chem. 1995, 60, 2502-2505.
117. Qin, Y.; Shah, S.; Kiburu, I.; Jäkle, F. Polym. Prepr. 2005, 46 (2), 1026-1027.
118. Qin, Y.; Cheng, G.; Achara, O.; Parab, K.; Jäkle, F. Macromolecules 2004, 37, 7123-7131.
119. Herrema, J. K.; Wildeman, J.; Gill, R. E.; Wieringa, R. H.; van Hutten, P. F.; Hadziioannou, G. Macromolecules 1995, 28, 8102-8116.
120. Kamal, M. R.; Al-Taweel, S. A.; El-Abadelah, M. M.; Ajaj, K. M. A. Phosphorus, Sulfur Silicon Relat. Elem. 1997, 126, 65-74.
121. Murov, S. L., Carmichael, I., Hug, G. L., Eds. Handbook of Photochemistry. 2nd ed.; Marcel Dekker Inc.; New York, 1993.
122. Gans, P.; Sabatini, A.; Vacca, A. Talanta 1996, 43, 1739-1753.
123. Sheldrick, G.M. SADABS (2.01), Bruker/Siemens Area Detector Absorption Correction Program; Bruker AXS: Madison, WI, 1998.
124. Sheldrick, G. SHELXTL (5.10); Bruker XRD: Madison, WI.