Benzobisoxazole cruciforms: Heterocyclic fluorophores with spatially separated frontier molecular orbitals

Journal of Organic Chemistry

Volumn 76, Issue 24, 2011, Pages 10207-10219

  Lim, Jaebum ^a   Albright, Thomas A ^a   Martin, Benjamin R ^b   Miljanić, Ognjen S ^a  

^a University of Houston   (United States)

^b TEXAS STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION AND EMISSION SPECTROSCOPY; ANALYTES; BATHOCHROMIC SHIFT; CRYSTAL PACKINGS; ELECTRON-RICH; FRONTIER MOLECULAR ORBITALS; HIGHEST OCCUPIED MOLECULAR ORBITAL; HOMO-LUMO GAPS; HYBRID DENSITY FUNCTIONAL THEORY; LOWEST UNOCCUPIED MOLECULAR ORBITAL; OPTICAL RESPONSE; PHENYL GROUP; PHENYL SUBSTITUENTS; SENSING PLATFORMS; X-RAY DIFFRACTION STUDIES;

DENSITY FUNCTIONAL THEORY; EMISSION SPECTROSCOPY; MOLECULAR ORBITALS; OPTICAL PROPERTIES; ORGANIC POLYMERS; PROTONATION; X RAY DIFFRACTION;

SYNTHESIS (CHEMICAL);

ISOXAZOLE DERIVATIVE; PHENYL GROUP; PYRIDINE DERIVATIVE;

ARTICLE; ATOMIC EMISSION SPECTROMETRY; CHEMICAL STRUCTURE; CONJUGATION; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ELECTRON; PROTON TRANSPORT; SEPARATION TECHNIQUE; SUBSTITUTION REACTION; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY DIFFRACTION;

EID: 84055217216     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202107w     Document Type: Article

References (99)

1. (a) Functional Organic Materials: Syntheses, Strategies and Applications; Müller, T. J. J., Bunz, U. H. F., Eds.; Wiley-VCH: Weinheim, 2007.
2. (b) Electronic Materials, the Oligomer Approach; Mullen, K., Wegner, G., Eds.; Wiley-VCH: Weinheim, 1998.
3. (c) Fukui, K. Science 1982, 218, 747-754.
4. see: (a) Fahrni, C. J.; Yang, L.; VanDerveer, D. G. J. Am. Chem. Soc. 2003, 125, 3799-3812.
5. (b) Huang, H.-H.; Prabhakar, Ch.; Tang, K.-C.; Chou, P.-T.; Huang, G.-J.; Yang, J.-S. J. Am. Chem. Soc. 2011, 133, 8028-8039.
6. (a) Ohta, K.; Yamada, S.; Kamada, K; Slepkov, A D.; Hegmann, F. A.; Tykwinski, R. R; Shirtcliff, L. D.; Haley, M. M.; Sałek, P.; Gel'mukhanov, F.; Ågren, H. J. Phys. Chem. A 2011, 115, 105-117.
7. (b) Carroll, C. N; Naleway, J. J.; Haley, M. M.; Johnson, D. W. Chem. Soc. Rev. 2010, 39, 3875-3888.
8. (c) Spitler, E. L.; Haley, M. M. Tetrahedron 2008, 64, 11469-11474.
9. (d) Spitler, E. L.; Monson, J. M.; Haley, M. M. J. Org. Chem. 2008, 73, 2211-2223.
10. (e) Spitler, E. L.; Shirtcliff, L. D.; Haley, M. M. J. Org. Chem. 2007, 72, 86-96.
11. (f) Bhaskar, A.; Guda, R; Haley, M. M.; Goodson, T. III. J. Am. Chem. Soc. 2006, 128, 13972-13973.
12. (g) Marsden, J. A.; Miller, J. J.; Shirtcliff, L. D.; Haley, M. M. J. Am. Chem. Soc. 2005, 127, 2464-2476.
13. (h) Miller, J. J.; Marsden, J. A; Haley, M. M. Synlett 2004, 165-168.
14. (a) Davey, E. A.; Zucchero, A. J.; Trapp, O.; Bunz, U. H. F. J. Am. Chem. Soc. 2011, 133, 7716-7718.
15. (b) McGrier, P. L.; Solntsev, K. M.; Zucchero, A J.; Miranda, O. R; Rotello, V. M.; Tolbert, L. M.; Bunz, U. H. F. Chem.-Eur. J. 2011, 17, 3112-3119.
16. (c) Zucchero, A. J.; McGrier, P. L.; Bunz, U. H. F. Acc. Chem. Res. 2010, 43, 397-408.
17. (d) Tolosa, J.; Solntsev, K. M.; Tolbert, L. M.; Bunz, U. H. F. J. Org. Chem. 2010, 75, 523-534.
18. (e) Zucchero, A J.; Shiels, R A; McGrier, P. L.; To, M. A; Jones, C. W.; Bunz, U. H. F. Chem.-Asian J. 2009, 4, 262-269.
19. (f) Tolosa, J.; Bunz, U. H. F. Chem.-Asian J. 2009, 4, 270-276.
20. (g) McGrier, P. L.; Solntsev, K. M.; Miao, S.; Tolbert, L. M.; Miranda, O. R; Rotello, V. M.; Bunz, U. H. F. Chem.-Eur. J. 2008, 14, 4503-4510.
21. (h) Tolosa, J.; Zucchero, A. J.; Bunz, U. H. F. J. Am. Chem. Soc. 2008, 130, 6498-6506.
22. (i) Brombosz, S. M.; Zucchero, A. J.; Phillips, R L.; Vasquez, D.; Wilson, A.; Bunz, U. H. F. Org. Lett. 2007, 9, 4519-4522.
23. (j) Hauck, M.; Schönhaber, J.; Zucchero, A. J.; Hardcastle, K. I.; Müller, T. J. J.; Bunz, U. H. F. J. Org. Chem. 2007, 72, 6714-6725.
24. (k) McGrier, P. L.; Solntsev, K. M.; Schonhaber, J.; Brombosz, S. M.; Tolbert, L. M.; Bunz, U. H. F. Chem. Commun. 2007, 2127-2129.
25. (l) Zucchero, A J.; Wilson, J. N; Bunz, U. H. F. J. Am. Chem. Soc. 2006, 128, 11872-11881.
26. (m) Gerhardt, W. W.; Zucchero, A J.; Wilson, J. N; South, C. R; Bunz, U. H. F.; Weck, M. Chem. Commun. 2006, 2141-2143.
27. (n) Wilson, J. N; Bunz, U. H. F. J. Am. Chem. Soc. 2005, 127, 4124-4125.
28. (o) Wilson, J. N; Smith, M. D.; Enkelmann, V.; Bunz, U. H. F. Chem. Commun. 2004, 1700-1701.
29. (p) Wilson, J. N; Hardcastle, K I.; Josowicz, M.; Bunz, U. H. F. Tetrahedron 2004, 60, 7157-7167.
30. (q) Wilson, J. N; Josowicz, M.; Wang, Y.; Bunz, U. H. F. Chem. Commun. 2003, 2962-2963.
31. Kang, H; Evmenenko, G; Dutta, P.; Clays, K.; Song, K.; Marks, T.J. J. Am. Chem. Soc. 2006, 128, 6194-6205.
32. (b) Kang, H; Zhu, P.; Yang, Y.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 15974-15975.
33. (a) Gisselbrecht, J. P.; Moonen, N. N. P.; Boudon, C.; Nielsen, M. B.; Diederich, F.; Gross, M. Eur. J. Org. Chem. 2004, 2959-2972.
34. (b) Mitzel, F.; Boudon, C.; Gisselbrecht, J. P.; Seiler, P.; Gross, M.; Diederich, F. Helv. Chim. Acta 2004, 87, 1130-1157.
35. (c) Diederich, F. Chem. Commun. 2001, 219-227.
36. (d) Gobbi, L.; Seiler, P.; Diederich, F. Angew. Chem., Int. Ed. 1999, 38, 674-678.
37. (e) Hilger, A.; Gisselbrecht, J.-P.; Tykwinski, R R; Boudon, C.; Schreiber, M.; Martin, R E.; Luthi, H. P.; Gross, M.; Diederich, F. J. Am. Chem. Soc. 1997, 119, 2069-2078.
38. (f) Bosshard, C.; Spreiter, R; Gunter, P.; Tykwinski, R R; Schreiber, M.; Diederich, F. Adv. Mater. 1996, 8, 231-234.
39. (g) Tykwinski, R R.; Schreiber, M.; Carlon, R P.; Diederich, F.; Gramlich, V. Helv. Chim. Acta 1996, 79, 2249-2281.
40. (h) Anthony, J.; Boldi, A. M.; Rubin, Y.; Hobi, M.; Gramlich, V.; Knobler, C. B.; Seiler, P.; Diederich, F. Helv. Chim. Acta 1995, 78, 13-45.
41. (i) Zhao, Y. M.; Tykwinski, RRJ. Am. Chem. Soc. 1999, 121, 458-459.
42. (j) Eisler, S.; Tykwinski, RRJ. Am. Chem. Soc. 2000, 122, 10736-10737.
43. (k) Zhao, Y. M.; Ciulei, S. C.; Tykwinski, R R Tetrahedron Lett. 2001, 42, 7721-7723.
44. (a) Koenen, J.-M.; Bilge, A.; Allard, S.; Alle, R; Meerholz, K.; Scherf, U. Org. Lett. 2009, 11, 2149-2152.
45. (b) Pina, J.; Seixas de Melo, J.; Burrows, H. D.; Galbrecht, F.; Bilge, A; Kudla, C. J.; Scherf, U. J. Phys. Chem. B 2008, 112, 1104-1111.
46. (c) Zen, A; Bilge, A; Galbrecht, F.; Alle, R; Meerholz, K.; Grenzer, J.; Neher, D.; Scherf, U.; Farrell, T. J. Am. Chem. Soc. 2006, 128, 3914-3915.
47. (d) Bilge, A; Zen, A.; Forster, M.; Li, H.; Galbrecht, F.; Nehls, B. S.; Farrell, T.; Neher, D.; Scherf, U. J. Mater. Chem. 2006, 16, 3177-3182.
48. Mangalum, A.; Gilliard, R J. Jr.; Hanley, J. M.; Parke, A. M.; Smith, R C. Org. Biomol. Chem. 2010, 8, 5620-5627.
49. Hu, J.-y.; Era, M.; Elsegood, M. R J.; Yamato, T. Eur. J. Org. Chem. 2010, 72-79.
50. Cho, M. J.; Park, S.S.; Yang, Y. S.; Kim, J. H.; Choi, D. H. Synth. Met. 2010, 160, 1754-1760.
51. (a) Grunder, S.; Huber, R; Wu, S.; Schönenberger, C.; Calame, M.; Mayor, M. Chimia 2010, 64, 140-144.
52. (b) Grunder, S.; Huber, R; Wu, S.; Schonenberger, C.; Calame, M.; Mayor, M. Eur. J. Org. Chem. 2010, 833-845.
53. (c) Grunder, S.; Huber, R; Horhoiu, V.; Gonzalez, M. T.; Schonenberger, C.; Calame, M.; Mayor, M. J. Org. Chem. 2007, 72, 8337-8343.
54. (d) Błaszczyk, A.; Fischer, M.; von Hanisch, C.; Mayor, M. Eur. J. Org. Chem. 2007, 2630-2642.
55. (a) Jennum, K.; Vestergaard, M.; Pedersen, A H.; Fock, J.; Jensen, J.; Santella, M.; Led, J. J.; Kilså, K.; Bjørnholm, T.; Nielsen, M. B. Synthesis 2011, 539-548.
56. (b) Vestergaard, M.; Jennum, K.; Sørensen, J. K.; Kilså, K; Nielsen, M. B. J. Org. Chem. 2008, 73, 3175-3183.
57. (c) Sorensen, J. K; Vestergaard, M.; Kadziola, A.; Kilsa, K; Nielsen, M. B. Org. Lett. 2006, 8, 1173-1176.
58. see: (a) Boydston, A. J.; Pecinovsky, C. S.; Chao, S. T.; Bielawski, C. W. J. Am. Chem. Soc. 2007, 129, 14550-14551.
59. (b) Boydston, A. J.; Vu, P. D.; Dykhno, O. L.; Chang, V; Wyatt, A R II; Stockett, A S.; Ritschdorff, E. T.; Shear, J. B.; Bielawski, C. W. J. Am. Chem. Soc. 2008, 130, 3143-3156.
60. (c) Boydston, A. J.; Khramov, D. M.; Bielawski, C. W. Tetrahedron Lett. 2006, 47, 5123-5125.
61. (d) Khramov, D. M.; Boydston, A. J.; Bielawski, C. W. Org. Lett. 2006, 8, 1831-1834.
62. (a) Klare, J. E.; Tulevski, G S.; Nuckolls, C. Langmuir 2004, 20, 10068-10072.
63. (b) Klare, J. E.; Tulevski, G S.; Sugo, K; de Picciotto, A.; White, K A.; Nuckolls, C. J. Am. Chem. Soc. 2003, 125, 6030-6031.
64. (c) Tlach, B. C.; Tomlinson, A L.; Bhuwalka, A; Jeffries-EL, M. J. Org. Chem. 2011, 76, 8670-8681.
65. (a) Feldman, A. K; Steigerwald, M. L.; Guo, X.; Nuckolls, C. Acc. Chem. Res. 2008, 41, 1731 - 1741.
66. (b) Tang, J.; Wang, Y.; Klare, J. E.; Tulevski, G S.; Wind, S. J.; Nuckolls, C. Angew. Chem., Int. Ed. 2007, 46, 3892-3895.
67. (c) Florio, G M.; Klare, J. E.; Pasamba, M. O.; Werblowsky, T. L.; Hyers, M.; Berne, B. J.; Hybertsen, M. S.; Nuckolls, C.; Flynn, G. W. Langmuir 2006, 22, 10003-10008.
68. (d) Guo, X.; Small, J. P.; Klare, J. E.; Wang, Y.; Purewal, M. S.; Tam, I. W.; Hong, B. H.; Caldwell, R; Huang, L.; O'Brien, S.; Yan, J.; Breslow, R; Wind, S. J.; Hone, J.; Kim, P.; Nuckolls, C. Science 2006, 311, 356-359.
69. (e) de Picciotto, A.; Klare, J. E.; Nuckolls, C.; Baldwin, K; A Erbe, A.; Willett, R Nanotechnology 2005, 16, 3110-3114.
70. Osowska, K; Mljanić, O. Š. Chem. Commun. 2010, 46, 4276-4278.
71. (a) Hegedus, L. S.; Odle, R R; Winton, P. M.; Weider, P. R J. Org. Chem. 1982, 47, 2607-2613.
72. (b) Weider, P. R; Hegedus, L. S.; Asada, H.; DAndreq, S. V J. Org. Chem. 1985, 50, 4276-4281.
73. (c) Osman, A-M.; Bassiouni, I. J. Org. Chem. 1962, 27, 558-561.
74. (a) Wolfe, J. F.; Arnold, F. E. Macromolecules 1981, 14, 909-915.
75. (b) Perry, R J.; Wilson, B. D.; Mller, R J. J. Org. Chem. 1992, 57, 2883-2887.
76. (c) Seha, Z.; Weis, C. D. Helv. Chim. Acta 1980, 63, 413-419.
77. (a) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250-6284.
78. (b) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283.
79. (a) Sonogashira, K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley: New York, 2002; Vol. 1, p 493 and references cited therein.
80. (b) Sonogashira, K; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467-4470.
81. Gaussian 09, Revision B.01: Frisch, M. J.; Trucks, G W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R; Scalmani, G; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A, Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K N.; Staroverov, V. N; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K; Rendell, A; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R E.; Yazyev, O.; Austin, A. J.; Cammi, R; Pomelli, C.; Ochterski, J. W.; Martin, R L.; Morokuma, K; Zakrzewski, V. G; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian, Inc., Wallingford, CT, 2010.
82. (a) Becke, A D. J. Chem. Phys. 1993, 98, 5648-5652.
83. (b) Lee, C.; Yang, W.; Parr, G R Phys. Rev. B 1988, 37, 785-789.
84. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994; p 214.
85. a values, see www.zirchrom.com/organic. html and www.scripps.edu/chem/baran/heterocycles/Essentials1-2009.pdf. Protonation of oxazole
86. See: Roldan, L. G; Litt, M. H. Acta Crystallogr. Sect B. 1968, B24, 1394.
87. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/
88. Spuest A. L. PLATON/SQUEEZE-A Multipurpose Crystallo-graphic Tool, Utrecht University, 2000.
89. Hunter, C. A; Sanders, J. K M. J. Am. Chem. Soc. 1990, 112, 5525-5534.
90. See: (a) Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48-76.
91. (b) Allen, F. H; Kennard, O.; Watson, D. G; Brammer, L.; Orpen, A G.; Taylor, R J. Chem. Soc, Perkin Trans. 2 1987, S1-S19.
92. (a) Nishio, M.; Hirota, M.; Umezawa, Y. The CH/π Interaction: Evidence, Nature, and Consequences, Wiley-VCH, New York, 1998.
93. (b) Umezawa, Y.; Tsuboyama, S.; Honda, K; Uzawa, J.; Nishio, M. Bull. Chem. Soc. Jpn. 1998, 71, 1207-1213.
94. (c) Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665-8701.
95. (a) Lee, W.-H.; Lee, H.; Kim, J.-A.; Choi, J.-H.; Cho, M.; Jeon, S.-J.; Cho, B. R. J. Am. Chem. Soc. 2001, 123, 10658-10667.
96. (b) Zyss, J.; Ledoux, I. Chem. Rev. 1994, 94, 77-105.
97. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London/Orlando, 1985; pp 18.
98. Leonard, K. A.; Nelen, M. I.; Anderson, L. T.; Gibson, S. L.; Hilf, R.; Detty, M. R. J. Med. Chem. 1999, 42, 3942-3952.
99. Ziessel, R.; Suffert, J.; Youinou, M.-T. J. Org. Chem. 1996, 6, 6535-6546.