Intermolecular interactions in π-stacked conjugated molecules. Synthesis, structure, and spectral characterization of alkyl bithiazole oligomers

Journal of the American Chemical Society

Volumn 125, Issue 17, 2003, Pages 5040-5050

  Koren, Amy B ^a   Curtis, M David ^a   Francis, Anthony H ^a   Kampf, Jeff W ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTALLINE MATERIALS; ELECTRONIC DENSITY OF STATES; EXCITONS; MOLECULES; MONTE CARLO METHODS; SUBSTITUTION REACTIONS;

SIDE CHAINS;

OLIGOMERS;

4,4',4'',4''' TETRAKIS(2 PROPENOXYMETHYL) 2,2',5',5'',2'',2''' QUATERTHIAZOLE; 4,4',4'',4''' TETRAKIS(3 HYDROXYPROPYLOXYMETHYL) 2,2',5',5'',2'',2''' QUATERTHIAZOLE; ALKYL GROUP; OLIGOMER; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; DIMERIZATION; ENERGY; LIGHT EMITTING DIODE; MOLECULAR INTERACTION; OLIGOMERIZATION; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

EID: 0037473516     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029216m     Document Type: Article

References (98)

1. (a) Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adu. Mater. 2002, 14, 99
2. (b) Horowitz, G. Adv. Mater. 1998, 10, 365.
3. (c) Horowitz, G. J. Mater. Chem. 1999, 9, 2021.
4. (d) Katz, H. E.; Bao, Z. J. Phys. Chem. B 2000, 104. 671.
5. (e) Lovinger, A. J.; Rothberg, L. J. J. Mater. Res. 1996. 11, 1581. (2)
6. (a) Hudson, A. J.; Weaver, M. S. In Functional Organic and Polymeric Materials; Richardson, T. H., Ed.; John Wiley & Sons: New York, 2000.
7. (b) Mitschke, U.; Bäuerle, P. J. Mater. Chem. 2000, 10, 1471.
8. Kaneko, M. In Handbook of Organic Conductive Molecules and Polymers, Vol. 4; Nalwa, H. S., Ed.; Wiley: New York, 1997.
9. (a) Brabec, C. J.; Sariciftci, S. N. Monatsh. Chem. 2001, 132 (4), 421.
10. (b) Shirota, Y. J. Mater. Chem. 2000, 10, 1.
11. Lin, Y.-Y.; Gundlach, D. J.; Nelson, S.; Jackson, T. N. IEEE Electron Device Lett. 1997, 18, 606.
12. Kittel, C. Introduction to Solid State Physics, 7th Ed.; John Wiley & Sons: New York, 1996; Chapters 7-9.
13. (a) Cornil, J.; Beljonne, D.; Calbert, J.-P.; Brédas, J.-L. Adv. Mater. 2001, 13, 1053.
14. (b) Brédas, J.-L.; Beljonne, D.; Cornil, J.; Calbert, J.-Ph.; Shuai, Z.; Silbey, R. Synth. Met. 2002, 125, 107.
15. (a) Holstein. T. Ann. Phys. 1959, 8, 325.
16. (b) see ref 8a, 343.
17. (a) Campbell, R. B.; Trotter, J.; Robertson, J. M. Acta Crystallogr. 1961, 14, 705.
18. (b) Horowitz, G.; Bachet, B.; Yassar, A.; Lang, P.; Demanze, F.; Fave, J. L.; Garnier, F. Chem. Mater. 1995, 7, 1337.
19. (c) Siegrist, T.; Fleming, R. M.; Haddon, R. C.; Laudise, R. A.; Lovinger, A. J.; Katz, H. E.; Bridenbaugh, P.; Davis, D. D. J. Mater. Res. 1995, 10, 2170.
20. (a) Sirringhaus, H.; Brown, P. J.; Friend, R. H.; Nielsen, M. M.; Bechgaard, K.; Langeveld-Voss, B. M. W.; Spierling, A. J. H.; Jansen, R. A. J.; Meier, E. W.; Herwig, P.; de leeuw, D. M. Nature 1999, 401, 685.
21. (b) Österbacka, R.; An, C. P.; Jiang, X. M.; Vardeny, Z. V. Science 2000, 287, 839.
22. (c) Lee, K.; Heeger, A. J. Synth. Met. 2002, 128, 279.
23. Pope, M.; Swenberg, C. E. Electronic Processes in Organic Crystals and Polymers. 2nd Ed.; Oxford University Press: New York, 1999.
24. (a) Pappenfus, T. M.; Chesterfield, R. J.; Frisbie, C. D.; Mann, K. R.; Casado, J.; Raff, J. D.; Miller, L. L. J. Am. Chem. Soc. 2002, 124, 4184.
25. (b) Li, X.-C.; Serringhaus, H.; Garnier, F.; Holmes, A. B.; Moratti, S. C.; Feeder. N.; Clegg, W.; Teat, S. J.; Friend, R. H. J. Am. Chem. Soc. 1998, 120, 2206.
26. (a) Hu, W. P.; Liu, Y. Q.; Xu, Y.; Liu, S. G.; Zhou, S. Q.; Zhu, D. B. Synth. Met. 1999, 104, 19.
27. (b) Horowitz, G. Adv. Mater. 1998, 10, 365.
28. (c) Reitzel, N.; Greve, D. R.; Kjaer, K.; Hows, P. B.; Jayaraman, M.; Savoy, S.; MeCullough, R. D.; McDevitt, J. T.; Bjomholm, T. J. Am. Chem. Soc. 2000, 122, 5788.
29. Yamamoto, T.; Maruyama, T.; Zhou, Z.; Ito, T.; Fukuda, T.; Yoneda, Y.; Begum, F.; lkeda, T. S.; Tahezoe, H.; Fukuda, A.; Kubota, K. J. Am. Chem. Soc. 1994, 116, 4832.
30. (a) Lee, J.; Curtis, M. D.; Kampf, J. W. Macromolecules 2000, 33, 2136.
31. (b) Gonzalez Ronda, L.; Martin, D. C.; Nanos, J. I.; Politis, J. K.; Curtis, M. D. Macromolecules 1999, 32, 4558.
32. (c) Nanos, J. I.; Kampf, J. W.; Curtis, M. D.; Gonzalez, L.; Martin, D. C. Chem. Mater. 1995, 7, 2232.
33. (d) Cao, J.; Kampf, J. W.; Curtis, M. D. Chem. Mater. 2003, 15, 404.
34. (e) Cao, J.; Curtis, M. D.; Kampf, J. W., manuscript in preparation.
35. Koren, A. B.; Curtis, M. D., manuscript in preparation.
36. Siegrist, T.; Kloc, C.; Schön, J. H.; Batlogg, B.; Haddon, R. C.; Berg, S.; Thomas, G. A. Angew. Chem., Int. Ed. 2001, 40, 1732.
37. Davydov, A. S. The Theory of Molecular Excitons; Plenum Press: New York, 1971.
38. (a) McCullough, R. D.; Tristram-Nagle, S.; Williams, S. P.; Lowe, R. D.; Jayaraman, M. J. Am. Chem. Soc. 1993, 115, 4910.
39. (b) Sandstedt, C. A.; Rieke, R. D.; Eckhardt, C. J. Chem. Mater. 1995, 7, 1057-1059.
40. (c) Chen, T.; Wu, X.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 233-244.
41. McCullough, R. D.; Ewbank, P. C. In Handbook of Conducting Polymers; Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998; pp 243-247.
42. Politis, J. K.; Somoza, F. B.; Kampf, J. W.; Curtis, M. D., Gonzalez Ronda, L.; Martin, D. C. Chem. Mater. 1999, 11, 2274.
43. Politis, J. K.; Nemes, J. C.; Curtis, M. D. J. Am. Chem. Soc. 2001, 123, 2537.
44. (a) Bunz, U. H. F.; Enkelmann, V.; Kloppenburg, L.; Jones, D.; Shimizu, K. D.; Claridge, J. B.; zur Loye, H.-C.; Lieser, G. Chem. Mater. 1999, 11, 1416.
45. (b) Halkyard, C. E.; Rampey, M. E.; Kloppenburg, L.; Studer-Martinez, S. L.; Bunz, U. H. F. Macromolecules 1998, 31, 8655.
46. Politis, J. K.; Curtis, M. D.; Gonzalez Ronda, L.; Martin, D. C.; He, Y.; Kanicki, J. Chem. Mater. 1998, 10, 1713.
47. Huang, W.; Meng, H.; Yu, W.-L.; Pei, J.; Chen, Z.-K.; Lai, Y.-H. Macromolecules 1999, 32, 118.
48. (a) Yang, C.; Orfino, F. P.; Holdcroft, S. Macromolecules 1996, 29, 6510.
49. (b) Park, K. C.; Levon, K. Macromolecules 1997, 30, 3175.
50. (a) Lambda, J. J. S.; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11723-11736.
51. (b) Inganäs, O. Trends Polym. Sci. (Cambridge, U.K.) 1994, 2, 189-196.
52. (a) Sakurai, K.; Tachibana, H.; Shiga, N.; Terakura, C.; Matsumoto, M.; Tokura, Y. Phys. Rev. B 1997, 56, 9552.
53. (b) Danno, T.; Kuerti, J.; Kuzmany, H. Front. Polym. Res., [Proc. Int. Conf.], 1st 1991, 219-222.
54. (c) Yamamato, T.; Honda, K.; Ooba, N.; Tomaro, S. Macromolecules 1998, 31, 7.
55. (a) Spano, F. C.; Siddiqui, S. Chem. Phys. Lett. 1999. 314, 481.
56. (b) Spano, F. C. J. Chem. Phys. 2001, 114, 5374.
57. (c) Spano, F. C. J. Chem. Phys. 2002, 116, 5877.
58. (d) DiCésare, N.; Belletête, M.; Leclerc, M.; Durocher, G. Chem. Phys. Lett. 1998, 291, 487.
59. (e) Chen, L. H.; Geiger, C.; Perlstein, J.; Whitten, D. G. J. Phys. Chem. B 1999, 103, 9161.
60. (f) Langeveld-Voss, B. M. W.; Waterval, R. J. M.; Janssen, R. A. J.; Meijer, E. W. Macromolecules 1999, 32, 227.
61. (a) DiCesare, N.; Belletete, M.; Marrano, C.; Leclerc, M.; Durocher, G. J. Phys. Chem. 1999, 103, 795.
62. (b) DiCesare, N.; Belletete, M.; Leclerc, M.; Durocher, G. J. Phys. Chem. 1999, 103, 803.
63. (c) DiCesare, N.; Belletete, M.; Garcia, E. R.; Leclerc, M.; Durocher, G. J. Phys. Chem. 1999, 103, 3864.
64. (d) Beljonne, D.; Langeveld-Voss, B. M. W.; Shuai, Z.; Janssen, R. A. J.; Meskers, S. C. J.; Meijer, E. W.; Bredas, J. L. Synth. Met. 1999, 102, 912.
65. (e) Bosisio, R.; Botta, C.; Colombo, A.; Destri, S.; Porzio, W.; Grilli, E.; Tubino, R.; Bongiovanni, G.; Mura, A.; DiSilvestro, G. Synth. Met. 1997, 87, 23.
66. (f) Spooner, S. P.; Whitten, D. G. Proc. SPIE- Int. Soc. Opt. Eng., 1991, 1436, 82-91.
67. (g) Penner, T. L. J. Chim. Phys. Phys.Chim. Biol. 1988, 85 (11-12), 1081-1084.
68. (a) McRae, E. G.; Kasha, M. In Proceedings of the International Symposium on Physical Processess in Radiation Biology (East Lansing. MI, 1963); Augenstein, L., Mason, R., Rosenberg, B., Eds.; Academic Press: New York, 1964.
69. (b) Giacintov, N. E.; Swenberg, C. E. In Luminescence Spectroscopy; Lumb, M. D., Ed.; Academic Press: New York, 1978; p 239ff.
70. (c) Broude, V. L.; Rashba, E. I.; Sheka, E. F. Spectroscopy Specti-oscopy, of Molecular Excitons, Springer Series in Chemical Physics, No. 16; Goldanskii, V, I., Ed.; Springer-Verlag: Berlin and New York, 1985.
71. (d) Rebane, K. K. Impurity Spectra of Solids, Elementary Theory of Vibrational Structure (in Russ., translated by Scheir, J. S.); Plenum Press: New York, 1970.
72. (e) Kasha, M. Radiat. Res. 1963, 20, 55.
73. (a) Siddiqui, S.; Spano, F. C. Chem. Phys. Lett. 1999, 308, 99.
74. (b) Manas, E. S.; Spano, F. C. J. Chem. Phys. 1998, 109, 8087.
75. (c) McRae, E. G.; Kasha, M. J. Phys. Chem. 1958, 28, 721.
76. (d) Song, Q.; Evans, C. E.; Bohn, P. W. J. Phys. Chem. 1993, 97, 13736.
77. (e) Evans, C. E.; Song, Q.; Bohn, P. W. J. Phys. Chem. 1993, 97, 12302-12308.
78. (f) Muccini, M.; Lunedei, E.; Taliani, C.; Beljonne, D.; Cornil, J.; Bredas, J. L. J. Chem. Phys. 1998, 23, 10513.
79. The proper reference state may be obtained with a dilute dispersion of the quaterthiazole in a host lattice of quaterphenyl. See: Blanda, W. M., Ph.D. Thesis, University of Michigan, Ann Arbor, MI. 2000.
80. (a) Philpott, M. R. J. Chem. Phys. 1970, 54, 111.
81. (b) Philpott, M. R. J. Chem. Phys. 1971, 55, 2039.
82. (a) Makhov, D. V.; Egorov, V. V.; Bagatur'yants, A. A.; Alfimov M. V. Chem. Phys. Lett. 1995, 246, 371.
83. (b) Makhov, D. V.; Egorov, V. V.; Bagatur'yants, A. A.; Alfimov M. V. Mater. Sci. Eng. C 1998, C5, 311-315.
84. (c) Schreiber, M.; Toyozawa, Y. J. Phys. Soc. Jpn. 1982, 51, 1528.
85. (d) Fidder, H.; Terpstra, J.; Wiersma, D. A. J. Chem. Phys. 1991, 94, 7880.
86. This approximation assumes that the vibrational frequencies in the S〈inf〉0〈/inf〉 and S〈inf〉1〈/inf〉 states are identical, (ii) each vibronic band is broadened by the same extent, and (iii) all the other sources of line broadening are the same for absorption and emission. The width of the solution absorption spectrum cannot be used to estimate the extent of peak broadening due to all sources other than 4J, because the solution spectrum is the superposition of the spectra of all the rotamers in solution, whereas only the planar conformation is present in the crystalline solid. See: Curtis, M. D. Macromolecules 2001, 34, 7905.
87. Cornil, J.; Beljonne, D.; Shuai, Z.; Hagler, T. W.; Campbell, I.; Bradley, D. D. C.; Brédas, J. L.; Spangler, C. W.; Müllen, K. Chem. Phys. Lett. 1995, 247, 425.
88. (a) Hernandez, V.; Losada, S. C.; Casado, J.; Higuchi, H.; Navarrete, J. T. L. J. Phys. Chem. A 2000, 104, 661.
89. (b) Louarn, G.; Trznadel, M.; Buison, J. P.; Laska, J.; Pron, A.; Lapkowski, M.; Lefrant, S. J. Phys. Chem. A 1996, 100, 12532.
90. (c) Louarn, G.; Trznadel, M.; Zagorska, M.; Lapkowski, M.; Pron, A.; Buisson, J. P.; Lefrant, S. Synth. Met. 1997, 84, 579.
91. Cornil, J.; Beljonne, D.; Heller, C. M.; Campbell, I. H.; Laurich, B. K.; Smith, D. L.; Bradley, D. D. C.; Müllen, K.; Brédas, J. L. Chem. Phys. Lett. 1997. 278, 139.
92. (a) Yang, C.; Orfino, F. P.; Holdcroft, S. Macromolecules 1996, 29, 6510.
93. (b) Park, K. C.; Levon, K. Macromolecules 1997, 30, 3175.
94. (c) Prosa, T. J.; Winokur, M. J.; McCullough, R. D. Macromolecules 1996, 29, 3654.
95. (a) Yamamoto, T.; Lee, B.; Suganuma, H.; Sasaki, S. Polym. J. (Tokyo) 1998, 30, 853.
96. (b) Aasmundtveit, K. E.; Samuelsen, E. J.; Pettersson, L. A. A.; Inganäs, O.; Johansson, T.; Feidenhans'l, R. Synth. Met. 1999, 101, 561.
97. (c) Wegner, G. In Electronic Properties of Polymers; Kuzmany, H., Mehring, M., Roth, S., Eds.; Springer-Verlag, New York, 185.
98. Cao, J.; Curtis, M. D., submitted for publication.