Synthesis and properties of carborane-appended C3-symmetrical extended π systems

Journal of the American Chemical Society

Volumn 132, Issue 18, 2010, Pages 6578-6587

  Dash, Barada Prasanna ^a   Satapathy, Rashmirekha ^a   Gaillard, Elizabeth R ^a   Maguire, John A ^b   Hosmane, Narayan S ^a  

^a NORTHERN ILLINOIS UNIVERSITY   (United States)

^b SOUTHERN METHODIST UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS SOLUTIONS; BLUE LIGHT; CARBORANES; CONJUGATED SYSTEMS; FLUORESCENCE INTENSITIES; FLUORESCENCE QUANTUM YIELD; MASS LOSS; SILICON TETRACHLORIDE; SOLID-SOLID PHASE TRANSITIONS; SUZUKI COUPLING REACTION; THERMALLY STABLE; TRIMERIZATION; WATERSOLUBLE;

ACETYLATION; FLUORESCENCE; PALLADIUM; PHASE TRANSITIONS; SYNTHESIS (CHEMICAL);

SILICON COMPOUNDS;

2 CARBORANE; CARBORANE DERIVATIVE; CHLORIDE; PALLADIUM; SILICON; TETRACHLORIDE; UNCLASSIFIED DRUG;

ACETYLATION; AQUEOUS SOLUTION; ARTICLE; BLUE LIGHT; CATALYSIS; CHEMICAL STRUCTURE; DECAPITATION; FLUORESCENCE ANALYSIS; SUZUKI REACTION; SYNTHESIS; TEMPERATURE SENSITIVITY; THERMOSTABILITY;

EID: 77952042680     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja101845m     Document Type: Article

References (100)

1. For reviews see: Northrop, B. H., Zheng, Y.-R., Chi, K.-W., and Stang, P. J. Acc. Chem. Res. 2009, 42, 1554-1563
2. Saragi, T. P. I., Spehr, T., Siebert, A., Fuhrman-Lieker, T., and Salbeck, J. Chem. Rev. 2007, 107, 1011-1065
3. Lo, S.-C. and Burn, P. L. Chem. Rev. 2007, 107, 1097-1116
4. Hoeben, F. J. M., Jonkheijm, P., Meijer, E. W., and Schenning, A. P. H. J. Chem. Rev. 2005, 105, 1491-1546
5. Grayson, S. M. and Frechet, J. M. J. Chem. Rev. 2001, 101, 3819-3867
6. Laquai, F., Mishra, A. K., Ribas, M. R., Petrozza, A., Jacob, J., Akcelrud, L., Mullen, K., Friend, R. H., and Wegner, G. Adv. Funct. Mater. 2007, 17, 3231-3240
7. Watson, M. D., Jackel, F., Severin, N., Rabe, J. P., and Mullen, K. J. Am. Chem. Soc. 2004, 126, 1402-1407
8. Vijaylakshmi, N. and Maitra, U. Org. Lett. 2005, 7, 2727-2730
9. Weil, T., Reuther, E., and Mullen, K. Angew. Chem., Int. Ed. 2002, 41, 1900-1904
10. Kumar, S. Chem. Soc. Rev. 2006, 35, 83-109
11. Pisula, W., Kastler, M., Wasserfallen, D., Pakula, T., and Mullen, K. J. Am. Chem. Soc. 2004, 126, 8074-8075
12. Craats, A. M. V., Warman, J. M., Fechtenkotter, A., Brand, J. D., Harbison, M. A., and Mullen, K. Adv. Mater. 1999, 11, 1469-1472
13. Muller, G. R. G., Meiners, C., Enkelmann, V., Geerts, Y., and Mullen, K. J. Mater. Chem. 1998, 1, 61-64
14. Fox, M. E., Szoka, F. C., and Frechet, J. M. J. Acc. Chem. Res. 2009, 42, 1141-1151
15. Almutairi, A., Rossin, R., Shokeen, M., Hangooly, A., Ananth, A., Capoccia, B., Guillaudeu, S., Abendschein, D., Welch, M. J., and Frechet, J. M. J. Proc. Natl. Acad. Sci. U.S.A. 2009, 685-690
16. Nishimaya, N., Iriyama, A., Jang, W.-D., Miyata, K., Itaka, K., Inoue, Y., Takahashi, H., Yanagi, Y., Tamaki, Y., Koyama, H., and Kataoka, K. Nat. Mater. 2005, 934-941
17. Astruc, D., Orneals, C., and Ruiz, J. Acc. Chem. Res. 2008, 41, 841-856
18. Chi, Y., Scroggins, S. T., Boz, E., and Frechet, J. M. J. J. Am. Chem. Soc. 2008, 130, 17287-117289
19. Lemo, J., Heuze, K., and Astruc, D. Chem. Commun. 1999, 4351-4353
20. Kraft, M. L. and Moore, J. F. Science 2008, 320, 620-621
21. Zang, L., Che, Y., and Moore, J. F. Acc. Chem. Res. 2008, 41, 1596-1608
22. Li, S. S., Northrop, B. H., Yuan, Q.-H., Wan, L.-J., and Stang, P. J. Acc. Chem. Res. 2009, 42, 249-259
23. Zheng, Y.-R., Yang, H. B., Ghosh, K., Zhao, L., and Stang, P. J. Chem. Eur. J. 2009, 15, 7203-7214
24. Northrop, B. H., Yang, H.-B., and Stang, P. J. Chem. Commun. 2008, 5896-5908
25. Ghosh, K., Hu, J., White, H. S., and Stang, P. J. J. Am. Chem. Soc. 2009, 131, 6695-6697
26. Lee, J., Ghosh, K., and Stang, P. J. J. Am. Chem. Soc. 2009, 131, 12028-12029
27. For reviews see: Zhu, Y., Cheng, K. Y., Maguire, J. A., and Hosmane, N. S. Curr. Chem. Biol. 2007, 1, 141-149
28. Grimes, R. N. J. Chem. Educ. 2004, 81, 658-672
29. Plesek, J. Chem. Rev. 1992, 92, 269-278
30. Hawthorne, M. F. and Maderna, A. Chem. Rev. 1999, 99, 3421-3434
31. Teixidor, F., Vinas, C., Demonceau, A., and Nunez, R. Pure Appl. Chem. 2003, 75, 1305-1313
32. Valliant, J. F., Guenther, K. J., Arienne, S., King, S., Morel, P., Schaffer, P., Sogbein, O. O., and Stephenson, K. A. Coord. Chem. Rev. 2002, 232, 173-230
33. Dash, B. P., Satapathy, R., Maguire, J. A., and Hosmane, N. S. Chem. Commun. 2009, 3267-3269
34. Jude, H., Disteldorf, H., Fischer, S., Wedge, T., Hawkridge, A. M., Arif, A. M., Hawthorne, F., Muddiman, D. C., and Stang, P. J. J. Am. Chem. Soc. 2005, 127, 12131-12139
35. Das, N., Stang, P. J., Arif, A. M., and Campana, C. F. J. Org. Chem. 2005, 70, 10440-10446
36. Dash, B. P., Satapathy, R., Maguire, J. A., and Hosmane, N. S. Org. Lett. 2008, 10, 2247-2250 and references therein
37. Vyakaranam, K., Rana, G., Ratanasuwan, A., Hosmane, S. N., Maguire, J. A., and Hosmane, N. S. Organometallics 2002, 21, 3905-3912
38. Yoo, J., Hwang, J.-W., and Do, Y. Inorg. Chem. 2001, 40, 568-570
39. Gonzalez-Campo, A., Vinas, C., Teixidor, F., Nunez, R., Sillanpaa, R., and Kivekas, R. Macromolecules 2007, 40, 5644-5652
40. Cacchi, S., Fabrizi, G., Gavazza, F., and Goggiamani, A. Org. Lett. 2003, 5, 289-291
41. Bao, C., Lu, R., Jin, M., Xue, P., Tan, C., Xu, T., Liu, G., and Zhao, Y. Chem. Eur. J. 2006, 12, 3287-3294
42. Yang, J.-X., Tao, X.-T., Yuan, C. X., Yan, Y. X., Wang, L., Liu, Z., Ren, Y., and Jiang, M. H. J. Am. Chem. Soc. 2005, 127, 3278-3279
43. Cao, X.-Y., Liu, X.-H., Zhou, X.-H., Zhang, Y., Jiang, Y., Cao, Y., Cui, Y.-X., and Pei, J. J. Org. Chem. 2004, 69, 6050-6058
44. Vicente, H., Edwards, F., Shetty, S. J., Hou, Y., and Boggan, J. E. Bioorg. Med. Chem. 2002, 10, 481-492
45. Hao, E., Fabre, B., Fronczeka, F. R., and Vicente, M. G. H. Chem. Mater. 2007, 19, 6195-6205
46. Gomez, F. A. and Hawthorne, M. F. J. Org. Chem. 1992, 57, 1384-1390
47. Deng, L. and Xie, Z. Organometallics 2007, 26, 1832-1845
48. Xie, Z. Coord. Chem. Rev. 2006, 250, 259-272
49. Hosmane, N. S. and Maguire, J. A. Organometallics 2005, 24, 1356-1389
50. Hawthorne, M. F., Young, D. C., Garrett, D. A., Owen, D. A., Schwerin, S. G., Tebbe, F. N., and Wegner, P. A. J. Am. Chem. Soc. 1968, 90, 862-868
51. Hawthorne, M. F., Young, D. C., Andrews, T. D., Howe, D. V., Pilling, R. L., Pitts, A. D., Reintjes, M., Warren, L. F., and Wegner, P. A. J. Am. Chem. Soc. 1968, 90, 879-896
52. Kotha, S., Kasinath, D., Lahiri, K., and Sunoj, R.B. Eur. J. Org. Chem. 2004, 4003-4013
53. Finke, A. D. and Moore, J. F. Org. Lett. 2008, 10, 4851-4854
54. He, Q., Huang, H., Yang, J., Lin, H., and Bai, F. J. Mater. Chem. 2003, 13, 1085-1089
55. Belser, P., Zelewsky, A., Frank, M., Seel, C., Vogtle, F., Cola, L. D., Barigelletti, F., and Balzani, V. J. Am. Chem. Soc. 1993, 115, 4076-4086
56. Pang, J., Marcotte, E. J.-P., Seward, C., Brown, R. S., and Wang, S. Angew. Chem., Int. Ed. 2001, 40, 4042-4045
57. Miller, T. M., Neenan, T. X., Zayas, R., and Bair, H. E. J. Am. Chem. Soc. 1992, 114, 1018-1025
58. Okumoto, K. and Shirota, Y. Chem. Mater. 2003, 15, 699-707
59. Schmidt, B., Rinke, M., and Gusten, H. J. Photochem. Photobiol. A: Chem. 1989, 49, 131-135
60. Muller, M., Kubel, C., and Mullen, K. Chem. Eur. J. 1998, 4, 2099-2109
61. Turro, N. J. Modern Molecular Photochemistry; Benjamin/Cummings: Menlo Park, CA, 1978.
62. Birks, J. B. Photophysics of Aromatic Molecules; Wiley: London, 1970.
63. Kokado, K., Tokoro, Y., and Chujo, Y. Macromolecules 2009, 42, 2925-2930
64. Kokado, K., Tokoro, Y., and Chujo, Y. Macromolecules 2009, 42, 9238-9242
65. Kokado, K. and Chujo, Y. Macromolecules 2009, 42, 1418-1420
66. Peterson, J. J., Simon, Y. C., Coughlin, B., and Carter, K. R. Chem. Commun. 2009, 4950-4952
67. Hong, Y., Lam, J. W. Y., and Tang, B. Z. Chem. Commun. 2009, 4332-4353
68. We are also thankful to reviewers for valuable suggestions.
69. Bigger, S. W., Ghiggino, K. P., Meilak, G. A., and Verity, B. J. Chem. Educ. 1992, 69, 675-677
70. Barghouthi, S. A., Perrault, J., and Holmes, L. H., Jr. Chem. Educ. 1998, 3, 1-10
71. Bastiaens, P. I. H. and Squire, A. Trends Cell Biol. 1999, 9, 48-52
72. Nguyen, D. C., Keller, R. A., Jett, J. H., and Martin, J. C. Anal. Chem. 1987, 59, 2158-2161
73. Peck, K., Stryer, L., Glazer, A. N., and Mathies, R. A. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 4087-4091
74. Jose, J. and Burgess, K. J. Org. Chem. 2006, 71, 7835-7839
75. Rivas, B. L. and Maureira, A. Macromol. Symp. 2008, 270, 143-152
76. Schnurpfeil, G., Stark, J., and Wohrle, D. Dyes Pigm. 1995, 27, 339-350
77. Knaus, S. and Gruber, H. F. J. Macromol. Sci. A, Pure Appl. Chem. 1996, 33, 869-881
78. Patrick, M. J., Ernst, L. A., Waggoner, A. S., Thai, D., Tai, D., and Salama, G. Org. Biomol. Chem. 2007, 5, 3347-3353
79. Verma, S., Padmawar, P. A., Hauck, T., Canteenwala, T., Chiang, L. Y., and Pritzker, K. P. H. J. Macromol. Sci. A, Pure Appl. Chem. 2005, 42, 1497-1505
80. Biosselier, E., Orneals, Catia., Pianet, I., Aranzaes, R. J., and Astruc, D. Chem. Eur. J. 2008, 14, 5577-5587
81. Klok, H.-A., Hernandez, J. R., Becker, S., and Mullen, K. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 1572-1583
82. Stafforst, T. and Diederichsen, U. Eur. J. Org. Chem. 2007, 899-911
83. Hempel, K. and Heinze, K. Chem. Eur. J. 2009, 15, 1346-1358
84. Kohl, C., Weil, T., Qu, J., and Mullen, K. Chem. Eur. J. 2004, 10, 5297-5310
85. Quante, H., Schlichting, P., Rohr, U., Geerts, Y., and Mullen, K. Macromol. Chem. Phys. 1996, 197, 4029-4044
86. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Plenum Press: New York, 1986.
87. Lor, M., Thielemans, J., Viaene, L., Cotlet, M., Hofkens, J., Weil, T., Hampel, C., Mullen, K., Verhoeven, J. W., Auweraer, M. V., and De Schryver, F. C. J. Am. Chem. Soc. 2002, 124, 9918-9925
88. Hao, E., Fabre, B., Fronczeka, F. R., and Vicente, M. G. H. Chem. Commun. 2007, 4387-4389
89. Benhabbour, S. R., Parrott, M. C., Gratton, S. E. A., and Adronov, A. Macromolecules 2007, 40, 5678-5688
90. Farha, O. K., Spokoyny, A. M., Mulfort, K. L., Hawthorne, M. F., Mirkin, C. A., and Hupp, J. T. J. Am. Chem. Soc. 2007, 129, 12680-12681
91. Wriedt, M., Sellmer, S., and Nather, C. Dalton Trans. 2009, 7975-7984
92. Kostler, S., Zechner, B., Trathnigg, B., Fasl, H., Kern, W., and Ribitsch, V. J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 1499-1509
93. Duquesne, S., Bras, M. L., Bourbogot, S., Delobel, R., Camino, G., Eling, B., Lindsay, C., Roels, T., and Vezin, H. J. Appl. Polym. Sci. 2001, 82, 3262-3274
94. Rohr, U., Schlichting, P., Bohm, A., Gross, M., Meerholz, K., Brauchhle, C., and Mullen, K. Angew. Chem., Int. Ed. 1998, 37, 1434-1437
95. Ito, S., Wehmeier, M., Brand, J. D., Kubel, C., Epsch, R., Rabe, J. P., and Mullen, K. Chem. Eur. J. 2000, 6, 4327-4342
96. Chen, J., Anthony, J., and Martin, D. C. J. Phys. Chem. B 2006, 110, 16397-16403
97. Kaszynski, P., Pakhomov, S., Tesh, K. F., and Young, V. G., Jr. Inorg. Chem. 2001, 40, 6622-6631
98. Nagamine, T., Januszko, A., Kaszynski, P., Ohta, K., and Yasuyuki, E. J. Mater. Chem. 2006, 6, 3836-3843
99. Januszko, A., Kaszynski, P., and Gruner, B. Inorg. Chem. 2007, 46, 6078-6082
100. Kaszynski, P. and Douglas, A. G. J. Organomet. Chem. 1999, 581, 28-38