Pure and Applied Chemistry, 2012, Volume 84, No. 4, pp. 991-1004, References

Pure Appl. Chem., 2012, Vol. 84, No. 4, pp. 991-1004

http://dx.doi.org/10.1351/PAC-CON-11-10-23

Published online 2012-03-13

Synthesis of benzobisoxazole-based D-π-A-π-D organic chromophores with variable optical and electronic properties

James S. Klimavicz¹, Jared F. Mike¹, Achala Bhuwalka¹, Aimeé L. Tomlinson² and Malika Jeffries-EL¹*

¹ Department of Chemistry, Iowa State University, Ames, IA 50011, USA
² Department of Chemistry, North Georgia College & State University, Dahlonega, GA 30597, USA

References

1. A. R. Murphy, J. M. J. Frechet. Chem. Rev. 107, 1066 (2007). (http://dx.doi.org/10.1021/cr0501386)
2. A. Facchetti. Chem. Mater. 23, 733 (2010). (http://dx.doi.org/10.1021/cm102419z)
3. C. W. Tang, S. A. VanSlyke. Appl. Phys. Lett. 51, 913 (1987). (http://dx.doi.org/10.1063/1.98799)
4. R. H. Friend, R. W. Gymer, A. B. Holmes, J. H. Burroughes, R. N. Marks, C. Taliani, D. D. C. Bradley, D. A. Dos Santos, J. L. Bredas, M. Logdlund, W. R. Salaneck. Nature 397, 121 (1999). (http://dx.doi.org/10.1038/16393)
5. A. C. Grimsdale, K. Leok Chan, R. E. Martin, P. G. Jokisz, A. B. Holmes. Chem. Rev. 109, 897 (2009). (http://dx.doi.org/10.1021/cr000013v)
6. K. M. Coakley, M. D. McGehee. Chem. Mater. 16, 4533 (2004). (http://dx.doi.org/10.1021/cm049654n)
7. M. C. Scharber, D. Muehlbacher, M. Koppe, P. Denk, C. Waldauf, A. J. Heeger, C. J. Brabec. Adv. Mater. 18, 789 (2006). (http://dx.doi.org/10.1002/adma.200501717)
8. T. B. Singh, N. S. Sariciftci. Annu. Rev. Mater. Res. 36, 199 (2006). (http://dx.doi.org/10.1146/annurev.matsci.36.022805.094757)
9. S. R. Forrest. Nature 428, 911 (2004). (http://dx.doi.org/10.1038/nature02498)
10. G. Qian, B. Dai, M. Luo, D. Yu, J. Zhan, Z. Zhang, D. Ma, Z. Y. Wang. Chem. Mater. 20, 6208 (2008). (http://dx.doi.org/10.1021/cm801911n)
11. S. Ellinger, K. R. Graham, P. Shi, R. T. Farley, T. T. Steckler, R. N. Brookins, P. Taranekar, J. Mei, L. A. Padilha, T. R. Ensley, H. Hu, S. Webster, D. J. Hagan, E. W. Van Stryland, K. S. Schanze, J. R. Reynolds. Chem. Mater. 23, 3805 (2011). (http://dx.doi.org/10.1021/cm201424a)
12. H. A. M. van Mullekom, J. A. J. M. Vekemans, E. E. Havinga, E. W. Meijer. Mater. Sci. Eng., R 32, 1 (2001). (http://dx.doi.org/10.1016/S0927-796X(00)00029-2)
13. E. E. Havinga, W. ten Hoeve, H. Wynberg. Synth. Met. 55, 299 (1993). (http://dx.doi.org/10.1016/0379-6779(93)90949-W)
14. F. M. Pasker, S. M. Le Blanc, G. Schnakenburg, S. Höger. Org. Lett. 13, 2338 (2011). (http://dx.doi.org/10.1021/ol2005853)
15. J.-L. Wang, Q. Xiao, J. Pei. Org. Lett. 12, 4164 (2010). (http://dx.doi.org/10.1021/ol101754q)
16. S. Ko, R. Mondal, C. Risko, J. K. Lee, S. Hong, M. D. McGehee, J.-L. Bredas, Z. Bao. Macromolecules 43, 6685 (2010). (http://dx.doi.org/10.1021/ma101088f)
17. J. Mei, N. C. Heston, S. V. Vasilyeva, J. R. Reynolds. Macromolecules 42, 1482 (2009). (http://dx.doi.org/10.1021/ma802779m)
18. R. S. Loewe, R. D. McCullough. Chem. Mater. 12, 3214 (2000). (http://dx.doi.org/10.1021/cm000421f)
19. M. Al-Hashimi, M. A. Baklar, F. Colleaux, S. E. Watkins, T. D. Anthopoulos, N. Stingelin, M. Heeney. Macromolecules 44, 5194 (2011). (http://dx.doi.org/10.1021/ma200910a)
20. K. D. Belfield, M. V. Bondar, C. O. Yanez, F. E. Hernandez, O. V. Przhonska. J. Mater. Chem. 19, 7498 (2009). (http://dx.doi.org/10.1039/b820950b)
21. A. J. Epstein, Y. Z. Wang, S. W. Jessen, J. W. Blatchford, D. D. Gebler, L. B. Lin, T. L. Gustafson, T. M. Swager, A. G. MacDiarmid. Macromol. Symp. 116, 27 (1997). (http://dx.doi.org/10.1002/masy.19971160105)
22. S. Ko, R. Mondal, C. Risko, J. K. Lee, S. Hong, M. D. McGehee, J.-L. Bredas, Z. Bao. Macromolecules 43, 6685 (2010). (http://dx.doi.org/10.1021/ma101088f)
23. A. Abbotto, E. H. Calderon, M. S. Dangate, F. De Angelis, N. Manfredi, C. M. Mari, C. Marinzi, E. Mosconi, M. Muccini, R. Ruffo, M. Seri. Macromolecules 43, 9698 (2010). (http://dx.doi.org/10.1021/ma1017132)
24. C. Romero-Nieto, S. Merino, J. Rodríguez-López, T. Baumgartner. Chem.—Eur. J. 15, 4135 (2009). (http://dx.doi.org/10.1002/chem.200802482)
25. Y.-H. So, S. J. Martin, B. Bell, C. D. Pfeiffer, R. M. Van Effen, B. L. Romain, S. M. Lefkowitz. Macromolecules 36, 4699 (2003). (http://dx.doi.org/10.1021/ma021045i)
26. J. F. Wolfe. In Encyclopedia of Polymer Science and Engineering, Vol. 11, p. 601, John Wiley (1988).
27. M. M. Alam, S. A. Jenekhe. Chem. Mater. 14, 4775 (2002). (http://dx.doi.org/10.1021/cm020600s)
28. J.-W. Huang, S. J. Bai. J. Polym. Sci., Part B: Polym. Phys. 45, 988 (2007). (http://dx.doi.org/10.1002/polb.21099)
29. J. A. Osaheni, S. A. Jenekhe. Macromolecules 27, 739 (1994). (http://dx.doi.org/10.1021/ma00081a018)
30. S. Wang, Y. Chen, Q. Zhuang, X. Li, P. Wu, Z. Han. Macromol. Chem. Phys. 207, 2336 (2006). (http://dx.doi.org/10.1002/macp.200600469)
31. C. C. Wu, P. Y. Tsay, H. Y. Cheng, S. J. Bai. J. Appl. Phys. 95, 417 (2004). (http://dx.doi.org/10.1063/1.1632021)
32. S. A. Jenekhe, J. A. Osaheni, J. S. Meth, H. Vanherzeele. Chem. Mater. 4, 683 (1992). (http://dx.doi.org/10.1021/cm00021a034)
33. B. A. Reinhardt, M. R. Unroe, R. C. Evers. Chem. Mater. 3, 864 (1991). (http://dx.doi.org/10.1021/cm00017a023)
34. J. F. Mike, A. J. Makowski, M. Jeffries-EL. Org. Lett. 10, 4915 (2008). (http://dx.doi.org/10.1021/ol802011y)
35. J. F. Mike, A. J. Makowski, T. C. Mauldin, M. Jeffries-EL. J. Polym. Sci., Part A: Polym. Chem. 48, 1456 (2010). (http://dx.doi.org/10.1002/pola.23869)
36. J. F. Mike, K. Nalwa, A. J. Makowski, D. Putnam, A. L. Tomlinson, S. Chaudhary, M. Jeffries-EL. Phys. Chem. Chem. Phys. 13, 1338 (2011). (http://dx.doi.org/10.1039/c0cp00353k)
37. J. F. Mike, J. J. Intemann, M. Cai, T. Xiao, R. Shinar, J. Shinar, M. Jeffries-EL. Polym. Chem. 2, 2299 (2011). (http://dx.doi.org/10.1039/c1py00218j)
38. J. J. Intemann, J. F. Mike, M. Cai, S. Bose, T. Xiao, T. C. Mauldin, R. A. Roggers, J. Shinar, R. Shinar, M. Jeffries-EL. Macromolecules 44, 248 (2011). (http://dx.doi.org/10.1021/ma102010s)
39. B.-S. Chen, Y.-J. Chen, P.-T. Chou. J. Mater. Chem. 21, 4090 (2011). (http://dx.doi.org/10.1039/c0jm04032k)
40. L. Kong, J. Yang, X. Hao, H. Zhou, J. Wu, F. Hao, L. Li, S. Zhang, B. Jin, X. Tao, M. Jiang, Y. Tian. J. Mater. Chem. 20, 7372 (2010). (http://dx.doi.org/10.1039/c0jm00004c)
41. J. Motoyoshiya, Z. Fengqiang, Y. Nishii, H. Aoyama. Spectrochim. Acta, Part A 69, 167 (2008).
42. O.-K. Kim, K.-S. Lee, H. Y. Woo, K.-S. Kim, G. S. He, J. Swiatkiewicz, P. N. Prasad. Chem. Mater. 12, 284 (2000). (http://dx.doi.org/10.1021/cm990662r)
43. S. E. Blanco, E. I. Gasull, F. H. Ferretti. Spectrochim. Acta, Part A 59, 2985 (2003).
44. O. A. Kucherak, P. Didier, Y. Me?ly, A. S. Klymchenko. J. Phys. Chem. Lett. 1, 616 (2010). (http://dx.doi.org/10.1021/jz9003685)
45. E. L. Spitler, J. M. Monson, M. M. Haley. J. Org. Chem. 73, 2211 (2008). (http://dx.doi.org/10.1021/jo701740n)
46. D. V. Matyushov, R. Schmid, B. M. Ladanyi. J. Phys. Chem. B 101, 1035 (1997). (http://dx.doi.org/10.1021/jp961609i)
47. R. M. Adhikari, D. C. Neckers, B. K. Shah. J. Org. Chem. 74, 3341 (2009). (http://dx.doi.org/10.1021/jo9002757)
48. W. R. Salaneck. J. Electron Spectrosc. Relat. Phenom. 174, 3 (2009). (http://dx.doi.org/10.1016/j.elspec.2009.03.024)
49. T. Miyamae, D. Yoshimura, H. Ishii, Y. Ouchi, T. Miyazaki, T. Koike, T. Yamamoto, Y. Muramatsu, H. Etori, T. Maruyama, K. Seki. Synth. Met. 84, 939 (1997). (http://dx.doi.org/10.1016/S0379-6779(96)04220-8)
50. S. Lois, J.-C. Florès, J.-P. Lère-Porte, F. Serein-Spirau, J. J. E. Moreau, K. Miqueu, J.-M. Sotiropoulos, P. Baylère, M. Tillard, C. Belin. Eur. J. Org. Chem. 4019 (2007). (http://dx.doi.org/10.1002/ejoc.200601114)
51. C. Hansch, A. Leo, R. W. Taft. Chem. Rev. 91, 165 (1991). (http://dx.doi.org/10.1021/cr00002a004)
52. J. Casanovas, D. Zanuy, C. Alema?n. Macromolecules 41, 3919 (2008). (http://dx.doi.org/10.1021/ma800174b)
53. B. C. Tlach, A. e. L. Tomlinson, A. Bhuwalka, M. Jeffries-EL. J. Org. Chem. 76, 8670 (2011). (http://dx.doi.org/10.1021/jo201078w)
54. R. F. Kubin, A. N. Fletcher. J. Lumin. 27, 455 (1982). (http://dx.doi.org/10.1016/0022-2313(82)90045-X)
55. Y. Gao, J. Wu, Y. Li, P. Sun, H. Zhou, J. Yang, S. Zhang, B. Jin, Y. Tian. J. Am. Chem. Soc. 131, 5208 (2009). (http://dx.doi.org/10.1021/ja808606d)
56. M. Jeffries-EL, G. Sauve, R. D. McCullough. Macromolecules 38, 10346 (2005). (http://dx.doi.org/10.1021/ma051096q)
57. R. D. McCullough, S. Tristam-Nagle, S. P. Williams, R. D. Lowe, M. Jayaraman. J. Am. Chem. Soc. 115, 4910 (1993). (http://dx.doi.org/10.1021/ja00064a070)

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Synthesis of benzobisoxazole-based D-π-A-π-D organic chromophores with variable optical and electronic properties

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Synthesis of benzobisoxazole-based D-π-A-π-D organic chromophores with variable optical and electronic properties

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