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130.98, 128.50, 128.35, 127.77, 127.44, 127.24, 126.66, 126.23, Commission, India for providing Senior Research Fellowship
125.95, 123.94, 123.49, 123.42, 123.27, 120.34, 112.38; HRMS (UGC-SRF).
calcd for C56H37N4 [M + H]+: 765.3013, found 765.2998; anal.
calcd for C56H36N4: C, 87.93; H, 4.74; N, 7.32. Found: C, 87.80;
References
H, 4.87; N, 7.32.
N3,N3,N6,N6-Tetrakis(4-methoxyphenyl)tribenzo[a,c,i]
phenazine-3,6-diamine (4). Dark red solid, yield: 135 mg (69%);
1 C. W. Tang and S. A. VanSlyke, Appl. Phys. Lett., 1987, 51, 913.
2 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,
mp 299 C; FT-IR (KBr, nmax cmꢀ1): 3089.20, 2929.90, 1597.34,
ꢁ
1499.89, 1234.89, 823.67, 715.23; 1H NMR (300 MHz, CDCl3,
d ppm): 9.04 (2H, d, J ¼ 9.0 Hz, aromatic), 8.73 (2H, s, aromatic),
8.09 (2H, dd, J ¼ 3.0 Hz, aromatic), 7.49 (2H, dd, J ¼ 3.0 Hz,
aromatic), 7.45 (2H, d, J ¼ 9.0 Hz, aromatic), 7.20 (2H, d, J ¼ 3.0
Hz, aromatic), 7.17 (2H, d, J ¼ 3.0 Hz, aromatic), 7.11 (6H, d, J ¼
9.0 Hz, aromatic), 6.83 (8H, d, J ¼ 9.0 Hz, aromatic), 3.83 (12H,
s, –OCH3); 13C NMR (75 MHz, CDCl3, d ppm): 156.58, 150.98,
143.88, 139.79, 138.85, 133.47, 133.42, 128.34, 127.64, 127.25,
126.55, 125.84, 122.87, 119.57, 114.79, 111.64, 55.42; HRMS
calcd for C52H41N4O4 [M + H]+: 785.3122, found 785.3218; anal.
calcd for C52H40N4O4: C, 79.57; H, 5.14; N, 7.14; O, 8.15. Found:
C, 79.60; H, 5.11; N, 7.19; O, 8.12.
J. L. Bredas, M. Logdlund and W. R. Salaneck, Nature,
1999, 397, 121.
¨
3 M. A. Baldo, M. E. Thompson and S. R. Forrest, Nature, 2000,
403, 750.
4 J. E. Anthony, Angew. Chem., Int. Ed., 2008, 47, 452.
5 M. Gratzel, Acc. Chem. Res., 2009, 42, 1788.
6 H. Imahori, T. Umeyama and S. Ito, Acc. Chem. Res., 2009, 42,
1809.
7 Z. Ning and H. Tian, Chem. Commun., 2009, 5483.
8 A. P. Kulkarni, C. J. Tonzola, A. Babel and S. A. Jenekhe,
Chem. Mater., 2004, 16, 4556.
¨
9 Y. Shirota, J. Mater. Chem., 2005, 15, 75.
N3,N6-Diphenyl-N3,N6-bis(4-((E)-phenyldiazenyl)phenyl)tri- 10 A. Kra, A. C. Grimsdale and A. B. Holmes, Angew. Chem.,
benzo[a,c,i]phenazine-3,6-diamine (5). Dark brown solid, yield:
Int. Ed., 1998, 37, 402.
124 mg (57%); mp 297 ꢁC; FT-IR (KBr, nmax cmꢀ1): 3035.12, 11 C. H. Chen and C. W. Tang, Appl. Phys. Lett., 2001, 79, 3711.
1588.56, 1489.78, 1266.34, 1137.78, 698.45. 1H NMR (300 MHz, 12 C. Adachi, M. A. Baldo, M. E. Thompson and S. R. Forrest, J.
CDCl3, d ppm): 9.17 (2H, d, J ¼ 9.0 Hz, aromatic), 8.78 (2H, s,
Appl. Phys., 2001, 90, 5048.
aromatic), 8.10 (2H, dd, J ¼ 3.0 Hz, aromatic), 7.91 (4H, d, J ¼ 13 X. Zhang and S. A. Jenekhe, Macromolecules, 2000, 33, 2069.
7.2 Hz, aromatic), 7.88 (4H, d, J ¼ 8.7 Hz, aromatic), 7.66 (2H, d, 14 R. R. Reghu, H. K. Bisoyi, J. V. Graulevicius, P. Anjukandi,
J ¼ 1.8 Hz, aromatic), 7.53–7.43 (10H, m, aromatic), 7.30–7.08
(14H, m, aromatic); 13C NMR (75 MHz, CDCl3, d ppm): 152.89,
V. Gaidelis and V. Jankauskas, J. Mater. Chem., 2011, 48,
3039.
149.50, 149.46, 148.18, 146.18, 143.37, 138.85, 133.79, 133.16, 15 S. K. Kim, B. Yang, Y. I. Park, Y. Ma, J.-Y. Lee and
130.51, 129.76, 129.08, 128.42, 127.90, 127.07, 126.35, 125.41, K. H.-J. Park, Org. Electron., 2009, 10, 822.
125.24, 124.34, 124.29, 123.54, 123.15, 122.66, 116.11; HRMS 16 B. Yang, S. K. Kim, H. Xu, Y.-I. Park, H.-Y. Zhang, C. Gu,
calcd for C60H41N8 [M + H]+: 873.3496, found 873.3513; anal.
calcd for C60H40N8: C, 82.55; H, 4.62; N, 12.84. Found: C, 82.45;
H, 4.67; N, 12.89.
F. Z. Shen, C. L. Wang, D. D. Liu, X. D. Liu, M. Hanif,
S. Tang, W. J. Li, F. Li, J. C. Shen, J. W. Park and Y.-G. Ma,
ChemPhysChem, 2008, 9, 2601.
3,6-Dimorpholinotribenzo[a,c,i]phenazine (6). Yellow solid, 17 M. Y. Lai, C. H. Chen, W. S. Huang, J. T. Lin, T. H. Ke,
yield: 76 mg (60%); mp 358 ꢁC; FT-IR (KBr, nmax cmꢀ1): 2964.48,
L. Y. Chen, M. H. Tsai and C.-C. Wu, Angew. Chem., Int.
Ed., 2008, 47, 581.
1586.24, 1495.94, 1210.84, 1114.03, 908.81, 793.32, 726.17,
1
636.97; H NMR (300 MHz, CDCl3, d ppm): 9.16 (2H, d, J ¼ 9.0 18 J.-Y. Shen, X.-L. Yang, T.-H. Huang, J. T. Lin, T.-H. Ke,
Hz, aromatic), 8.75 (2H, s, aromatic), 8.10 (2H, dd, J ¼ 3.0 Hz,
aromatic), 7.61 (2H, s, aromatic), 7.51 (2H, dd, J ¼ 3.0 Hz,
L.-Y. Chen, C.-C. Wu and M.-C. P. Yeh, Adv. Funct. Mater.,
2007, 17, 983.
aromatic), 7.21 (2H, d, J ¼ 9.0 Hz, aromatic), 3.95 (8H, t, J ¼ 4.5 19 K. R. J. Thomas, J. T. Lin, Y.-T. Tao and C.-W. Ko, J. Am.
Hz), 3.40 (8H, t, J ¼ 4.5 Hz); 13C NMR (75 MHz, CDCl3, d ppm):
Chem. Soc., 2001, 123, 9404.
152.98, 143.67, 138.65, 133.60, 128.38, 128.15, 126.67, 125.95, 20 T.-H. Huang, J. T. Lin, L.-Y. Chen, Y.-T. Lin and C.-C. Wu,
125.07, 123.18, 116.24, 107.24, 66.85, 48.70; HRMS calcd for
Adv. Mater., 2006, 18, 602.
C
C
32H29N4O2 [M + H]+: 501.2285, found 501.2288; anal. calcd for 21 Y. S. Kwon, K. H. Lee, K. G. Young, J. H. Seo, Y. K. Kim and
32H28N4O2: C, 76.78; H, 5.64; N, 11.18; O, 6.39. Found: C, 76.60;
S. S. Yoont, J. Nanosci. Nanotechnol., 2009, 9, 7056.
22 Z. Jiang, Z. Liu, C. Yang, C. Zhong, J. Qin, G. Yu and Y. Liu,
Adv. Funct. Mater., 2009, 19, 987.
H, 5.83; N, 11.19; O, 6.38.
23 D. E. Loy, B. E. Koene and M. E. Thompson, Adv. Funct.
Mater., 2002, 12, 245.
Acknowledgements
The authors are greatly thankful to Micro-Analytical Laboratory, 24 K. R. J. Thomas, M. Velusamy, J. T. Lin, C. H. Chuen and
Department of Chemistry, University of Mumbai for providing Y. T. Tao, J. Mater. Chem., 2005, 15, 4453.
Instrumental facilities. We are sincerely thanks to Central 25 M. Jandke, P. Strohriegl, S. Berleb, E. Werner and
facility Centre, Department of Chemistry, IIT Bombay for W. Brutting, Macromolecules, 1998, 31, 6434.
providing HRMS Spectrum. Two of the authors (Azam M. 26 K. R. J. Thomas, J. T. Lin, Y. T. Tao and C. H. Chuen, Chem.
Shaikh and Bharat K. Sharma) is grateful to University Grants
Mater., 2002, 14, 2796.
94226 | RSC Adv., 2016, 6, 94218–94227
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