822
Z.F. Duan et al. / Chinese Chemical Letters 22 (2011) 819–822
The maximum absorption red-shifted about 6 nm from 338 to 344 nm, while the small peak at 410 nm red-shifted
about 5 nm–415 nm accompanied with obvious absorbance enhancement and the absorption edge underwent 13 nm
red-shifts. The compound 1 with the larger rigid core has strong p–p interactions in the solid state and may be a good
candidate material in organic electronic devices. Further studies on the application of this molecule to electronic
devices such as field effect transistors are currently underway.
Acknowledgments
The film investigated in this work was fabricated in the Micro Functional Device Research Center of the College of
Science and Technology, Nihon University.
References
[1] (a) S.C. Lo, P.L. Burn, Chem. Rev. 107 (2007) 1097;
(
b) A.R. Murphy, J.M.J. Fr e´ chet, Chem. Rev. 107 (2007) 1066.
[
[
[
[
[
[
2] Y. Didane, G.H. Mehl, A. Kumagai, et al. J. Am. Chem. Soc. 130 (2008) 17681.
3] T. Yamato, M. Fujimoto, A. Miyazawa, et al. J. Chem. Soc., Perkin Trans. I 8 (1997) 1201.
4] T. Yamato, A. Miyazawa, M. Tashiro, Chem. Ber. 126 (1993) 2505.
5] Y. Miura, E. Yamano, J. Org. Chem. 60 (1995) 1070.
6] P. Wilson, D. Lacey, S. Sharma, et al. Mol. Cryst. Liq. Cryst. 368 (2001) 279.
7] (a) J.D. Tovar, A. Rose, T.M. Swager, J. Am. Chem. Soc. 124 (2002) 7762;
(
(
(
b) Y. Zhou, W.J. Liu, W. Zhang, et al. J. Org. Chem. 71 (2006) 6822;
c) J. Pei, W.Y. Zhang, J. Mao, et al. Tetrahedron Lett. 47 (2006) 1551;
d) J.L. Brusso, O.D. Hirst, A. Dadvand, et al. Chem. Mater. 20 (2008) 2484.
1
[
8] Spectral data of compound 1: a yellow solid. mp 185–187 8C. H NMR (600 MHz, CDCl
3
): d 9.48 (s, 4H), 7.58 (s, 4H), 3.11 (t, 8H, J = 7.4 Hz),
): d 149.0,
1
.90–1.91 (m, 8H), 1.78 (s, 18H), 1.50–1.53 (m, 8H), 1.35–1.41(m, 16H), 0.92 (t, 12H, J = 7.2 Hz). C NMR (150 MHz, CDCl
+
47.3, 135.5, 132.9, 128.4, 124.3, 122.5, 122.0, 119.2, 36.0, 32.1, 31.7, 31.3, 30.6, 28.9, 22.6, 14.1. FAB-MS, m/z: [M] 974.3. Anal. Calcd. for
3
1
3
1
1
C
64
H
78
S
4
: C, 78.79; H, 8.06. Found: C, 78.62; H, 8.17. Spectral data of compound 2: a pale yellow solid. mp = 113–15 8C. H NMR (600 MHz,
): d 8.24 (s, 4H), 6.81 (d, 4H, J = 3.4 Hz), 6.71 (d, 4H, J = 3.4 Hz), 2.83 (t, 8H, J = 7.2 Hz), 1.67–1.70 (m, 8H), 1.35(s, 18H), 1.32–1.35
CDCl
3
13
(
m, 24H), 0.91 (t, 12H, J = 6.9 Hz). C NMR (150 MHz, CDCl
3
): d 148.3, 146.4, 137.7, 132.9, 131.1, 128.8, 123.4, 122.3, 35.4, 31.8, 31.7, 31.6,
0.1, 28.5, 22.7, 14.1. FAB-MS, m/z: [M] 978.6. Anal. Calcd. for C64 : C, 78.46; H, 8.44. Found: C, 78.68; H, 8.20. Spectral data of
): d 8.17 (s, 4H), 7.40 (dd, 4H, J = 5.2, 1.4 Hz), 7.05–7.08 (m, 8H), 1.33
+
3
82 4
H S
1
compound 10: a white solid. Mp > 300 8C. H NMR (600 MHz, CDCl
3
1
3
+
(
s, 18H). C NMR (150 MHz, CDCl
Anal. Calcd. for C40 : C, 74.72; H, 5.33. Found: C, 74.96; H, 5.18
9] (a) W.J. Liu, Y. Zhou, Y. Ma, et al. Org. Lett. 9 (2007) 4187;
3
): d 148.7, 140.1, 132.7, 131.0, 129.3, 126.4, 126.2, 122.8, 122.4, 35.4, 31.6. FAB-MS, m/z: [M] 642.2.
34 4
H S
[
(
(
b) Y. Zhou, W.J. Liu, Y. Ma, et al. J. Am. Chem. Soc. 129 (2007) 12386;
c) J. Luo, B. Zhao, H.S.O. Chan, et al. J. Mater. Chem. 20 (2010) 1932.