本研究在於開發新的缺電子性的材料。我們成功的將imidzole-
[1,2-a]pyrimidine 之二號碳上及三號碳上，進行C-C 鍵的偶合，合成
出兩系列化合物，其其螢光光色從藍到藍綠，在toluene 中的量子產
率大約4﹪~ 50﹪，此系列化合物經AC-2 量測，其HOMO 能階介於
5.42 eV~ 6.11 eV，並且經由UV 的edge 切線求得化合物的HOMO 與
LUMO 能階差，而估算出LUMO 能階，其LUMO 能階 介於2.47 eV
~ 2.94 eV。化合物2、3、6、14 並經單晶解析，證實其結構。其中除
化合物2 為三斜晶系外，化合物3、6 與14 皆為單斜晶系。化合物3
中之晶體中可發現分子有π-π interaction，imidzole[1,2-a]pyrimidine
環間距離為約3.36 Å，但僅存在於兩兩配對之分子，無法形成π-通
道( π-channel )。化合物6 則存在有分子間C-H…π interaction，距
離約為2.7 Å。化合物14 則是形成有趣的魚骨頭( herringbone )架構，
其π-π interaction 之距離分別是3.34 Å 與3.39 Å。

Electron-deficent organic materials containing imidazole[1,2-a]-
pyrimidine unit have been synthesized via C-C coupling at the C-2 and
C-3 sites of imidazole[1,2-a]pyrimidine unit. These compounds emit
from blue to green-blue and their quantum yields in toluene range from
4 to 50％. Based on the data from AC-2 measurement,and the 0-0
transition energy from UV spectra, the HOMO and LUMO energies were
calculated to be 5.42 ~ 6.11 eV and 2.47 ~ 2.94 eV, respectively. The
molecular structure of compounds 2, 3, 6 and 14 were confirmed by the
single crystal X-ray structural determination. The crystal system of 2 is
triclinic, that of all others is monoclinic. In the lattice of 3, there exists
9-9 interaction at a distance ~ 3.36 Å. However, such an interaction was
found in the paired molecules only. In 6, C-H…9 interaction with a
distance of 2.7 Å was observed. In comparison, compound 14 has
interesting herringbone packing in the lattice. The 9-9 interaction
distances for two different 9-channels are 3.34 Å and 3.39 Å,
respectively.

1. M. Pope, H. P. Kallmann, P. Mgnante, J. Chem. Phys. 1963, 38, 2042.
2. C. W. Tang, S. A. VanSlyke, Appl. Phys. Lett. 1987, 51, 913.
3. J. H. Burroughes, D. D. C. Bradley, A. R. Brown, R. N. Marks, K.
Mackey, R. H. Friend, P. L. Burns, A. B. Holmes, Nature, 1990, 347,
539.
4. http://china.nikkeibp.co.jp
5. T. Ishida, H. Kobayashi, Y. Nakato, J. Appl. Phys. 1993, 73, 4334.
6. Y. Sun, N. C. Giebink, H. Kanno, B. Ma, M. E. Thompson, S. R.
Forrest, Nature, 2006, 440, 908.
7. S. A. VanSlyke, C. H. Chen, C. W. Tang, Appl. Phys. Lett. 1996, 69,
2160.
8. J. Li, C. Ma, J. Tang, C. Lee, S. Lee, Chem. Mater. 2005, 17, 615-619.
9. P. M. Borsenberger, W. Mey, A. Chowdry, Appl. Phys. Lett. 1978, 49,
273.
10. K. R. Justin Thomas, M. Velusamy, J. T. Lin, Y. T. Tao,
C. H. Chuen, Adv. Funct. Mater. 2004, 14, 387.
11. G. Hughes, M. R. Bryce, J. Mater. Chem. 2005, 15, 94.
12. Y. Eamada, T. Sano, M. Fujita, T. Fujita, Y. Nishio, K. Shibata, Chem.
Lett. 1993, 905.
13. J. Shi, C. W. Tang, Appl. Phys. Lett. 1997, 70, 1665.
14. J. L. Brédas, R. Silbey, D. S. Boudreaux, R. R. Chance, J. Am. Chem.
Soc.1983, 105, 6555.
15. M. A. Baldo, D. F. O’Brien, Y. You, A. Shoustikov, S. Sibley, M. E.
Thompson, S. R. Forrest, Nature, 1998, 395, 151.
16. (a) K. A. King, P. J. Spellane, R. J. Watts, J. Am. Chem. Soc. 1985,
107, 1431.
(b) G. A. Crosby, J. Chem. Phys. 1967, 64, 160.
17. C. Adachi, P. C. Kwong, P. Djurovich, V. Adamovich, M. A. Baldo, M.
E. Thompson, S. R. Forrest, Appl. Phys. Lett. 2001, 79, 2082.
18. D. F. O’Brien, M. A. Baldo, M. E. Thompson, S. R. Forrest, Appl.
Phys. Lett. 1999, 74, 442.
19. C. Adachi, M. A. Baldo, S. R. Forrest, S. Lamansky, M. E. Thompson,
R. C. Kwong, J. Am. Chem. Soc. 2001, 123, 1622.
20. M. A. Baldo, S. Lamansky, P. E. Burrows, M. E. Thompson, S. R.
Forrest, Appl. Phys. Lett. 1999, 75, 4.
21. C. Adachi, R. C. Kwong, P. Djurovich, V. Adamovich, M. A. Baldo,
M. E. Thompson, S. R. Forrest, Appl. Phy. Lett. 2001, 78, 1622.
22. J. P. Puan, P. P. Sun, C. H. Cheng, Adv. Mater. 2003, 15, 224.
23. W. Li, D. P. Nelson, M. S. Jensen, R. S. Hoerrner, G. J. Javadi, D. Cai,
R. D. Larsen, Org. Lett., 2003, 5 ,4835.
24. J. G. Lombardino, J. Org. Chem., 1965, 30, 2403.
25. A. J. Elliott, H. Guzik, J. R. Soler, J. heterocycl. chem., 1982, 19,
1437.
26. K. R. Justin Thomas, J. T. Lin, C. P. Chang, C. H. Chuen,
C. C. Cheng, J. Chin. Chem. Soc.( Taipei ), 2002, 49, 833.
27. C. G. Bochet, C. Piguet, A. F. Williams, Helv. chim. acta., 1993, 76,
372.
28. (a) S. S. Sun, J. J. Wu, J. T. Lin, L. Lee, K. J. Lin, Y. F. Huang, Inorg.
Chem. 1995, 34, 2323.
(b) M. Brinkmann, G. Gadret, M. Muccini, C. Taliani, N. Masciocchi,
A. Sironi, J. Am. Chem. Soc. 2000, 122, 5147.
(c) M. A. Baldo, Z. G. Soos, S. R. Forrest, Chem. Phys. Lett. 2001,
347, 297.
29. H. lnada, Y. Shirota, J. Mater. Chem., 1993, 3, 319.
30. K. T. Wong, Y. Y. Chien, R. T. Chen, C. F. Wang, Y. T. Lin, H. H.
Chiang, P. Y. Hsieh, C. C. Wu, C. H. Chou, Y. O. Su, G. H. Lee, S.
M. Peng, J. Am. Chem. Soc. 2002, 124, 11576.