NJC
General procedure for the synthesis of compounds 2–6. C62H51N5O6:
Paper
C
77.40,
H
5.34,
N
7.28, O, 9.98. found:
A mixture of compound 1 (0.122 g, 0.25 mmol) and various C 77.42, H 5.33, N 7.19, O 10.06.
diarylamines (0.6 mmol) was dissolved in anhydrous tetra-
N3,N6,N11-Triphenyl-N6,N11,N11-tris(4-(E)-(phenyldiazenyl)phenyl)-
dibenzo[a,c]phenazine-3,6,11-triamine (5). Dark red solid, yield: 145
mg (53%), mp: 262 1C. FT-IR (KBr, nmax cmꢀ1): 3035.43, 1586.07,
hydrofuran (20 ml). To this solution, Pd2(dba)3 (20 mg,
0.02 mmol), SPhos (13 mg, 0.03 mmol) and t-BuONa (75 mg,
0.75 mmol) were added. The reaction mixture was continuously
stirred under a nitrogen atmosphere at 80 1C for 6 h. The reaction
mixture was then cooled to room temperature and extracted with
chloroform. The solid thus obtained was then purified by column
chromatography (eluent: n-hexane : chloroform ratio as 70 : 30) to
obtain a dark red to dark orange solid.
1
1488.55, 1269.42, 686.22; H NMR (300 MHz, CDCl3): d (ppm) =
9.12 (d, J = 9.0 Hz, 1H), 9.04 (d, J = 9.0 Hz, 1H), 8.08 (d, J = 9.0 Hz,
2H), 7.90–7.74 (m, 14H), 7.63 (d, J = 2.7 Hz, 1H), 7.60 (d, J = 2.7 Hz,
2H), 7.51–7.15 (m, 30H); 13C NMR (75 MHz, CDCl3): d (ppm) =
156.30, 152.89, 149.66, 148.93, 148.58, 148.41, 147.98, 147.90,
146.46, 146.34, 146.28, 143.15, 142.28, 141.95, 140.67, 139.42,
133.35, 132.85, 132.32, 131.88, 130.43, 129.91, 129.71, 129.05,
127.50, 127.38, 127.15, 126.39, 126.21, 125.80, 125.48, 125.23,
125.07, 124.40, 124.31, 123.75, 123.25, 123.14, 122.67, 122.62,
119.34, 116.48, 116.29, 116.28; HRMS: calcd for C75H52N11
[M + H]+ 1094.4323; found 1094.4411; elemental anal. calcd for
C75H51N11: C 81.22, H 4.70, N 14.08. found: C 81.32, H 4.63,
N 14.05.
N3,N3,N6,N6,N11,N11-Hexaphenyldibenzo[a,c]phenazine-3,6,11-
triamine (2). Dark orange solid, yield: 129 mg (66%), mp: 272 1C.
FT-IR (KBr, nmax cmꢀ1): 3033.43, 1585.98, 1485.72, 748.39,
691.76; 1H NMR (300 MHz, CDCl3): d (ppm) = 9.06 (d, J =
9.0 Hz, 1H), 8.99 (d, J = 9.0 Hz, 1H), 8.02 (d, J = 9.0 Hz, 1H),
7.62–7.63 (m, 3H), 7.55 (d, J = 9.0 Hz, 2H), 7.38–7.03 (m, 31H);
13C NMR (75 MHz, CDCl3): d (ppm) = 149.60, 149.31, 149.21,
147.98, 147.09, 147.07, 146.97, 143.18, 142.34, 142.28, 140.34,
138.83, 132.88, 132.24, 129.59, 129.40, 127.15, 125.58, 124.48,
124.21, 123.89, 123.79, 122.51, 122.19, 117.09, 115.59, 114.87,
114.62; HRMS: calcd for C56H40N5 [M + H]+; 782.3278 found
782.3293; elemental anal. calcd for C56H39N5: C 86.02, H 5.03,
N 8.96. found: C 86.12, H 4.93, N 8.95.
4,40,400-(Dibenzo[a,c]phenazine-3,6,11-triyl)trimorpholine (6).
Orange solid, yield: 82 mg (61%), mp: 223 1C. FT-IR (KBr,
nmax cmꢀ1): 3479.23, 2920.34, 2848.93, 1604.23, 1362.36,
1106.52, 685.90; 1H NMR (300 MHz, CDCl3): d (ppm) = 8.09
(d, J = 9.0 Hz, 1H), 7.79 (s, 2H), 7.55 (d, J = 2.4 Hz, 1H), 7.52
(d, J = 2.4 Hz, 1H), 7.43 (d, J = 2.1 Hz, 1H), 7.32 (d, J = 8.1 Hz,
2H), 7.25 (s, 1H), 3.97 (t, J = 4.5 Hz, 12H,), 3.42 (t, J = 4.5 Hz,
12H); 13C NMR (75 MHz, CDCl3): d (ppm) = 152.48, 152.15,
151.23, 143.49, 142.19, 140.01, 132.40, 132.31, 129.65, 127.21,
121.88, 121.57, 116.51, 116.35, 116.20, 109.38, 108.93, 108.28,
107.19, 107.03, 66.92, 66.81, 49.41, 49.14; HRMS: calcd for
N3,N6,N11-Tri(naphthlen-1-yl)-N6,N11,N11-triphenyldibenzo[a,c]-
phenazine-3,6,11-triamine (3). Red solid, yield: 139 mg (60%),
mp: 238 1C. FT-IR (KBr, nmax cmꢀ1): 3055.03, 1590.24, 1488.12,
1
1357.10, 770.23, 693.04; H NMR (300 MHz, CDCl3): d (ppm) =
9.00 (d, J = 9.0 Hz, 1H), 8.97 (d, J = 9.0 Hz, 1H), 7.96–7.73
(m, 10H), 7.51–6.97 (m, 33H); 13C NMR (75 MHz, CDCl3):
d (ppm) = 150.06, 149.65, 149.06, 147.45, 147.38, 147.26,
145.42, 143.17, 142.82, 142.71, 142.61, 142.26, 140.15, 138.43,
135.40, 135.16, 132.91, 132.20, 131.13, 131.08, 131.01, 129.42,
129.18, 128.51, 128.42, 127.56, 127.33, 127.21, 127.03, 126.99,
126.72, 126.53, 126.38, 126.30, 126.14, 125.23, 124.30, 123.97,
123.56, 123.41, 123.11, 123.04, 122.97, 122.90, 120.90, 120.60,
115.07, 112.75; HRMS: calcd for C68H46N5 [M + H]+ 932.3646;
found 932.3781; elemental anal. calcd for C68H45N5: C 87.62,
H 4.87, N 7.51. found: C 87.52, H 4.97, N 7.52.
C
32H34N5O3 [M + H]+ 536.2656; found 536.2650; elemental anal.
calcd for C32H33N5O3: C 71.75, H 6.21, N 13.07, O, 8.96. found:
C 71.70, H 6.23, N 13.19, O 8.98.
Acknowledgements
The authors are greatly thankful to Micro-Analytical Laboratory,
Department of Chemistry, University of Mumbai for providing
Instrumental facilities. We are sincerely thanks to Central
facility Centre, Department of Chemistry, IIT Bombay for
providing HRMS Spectrum and National centre for Nanoscience
and Nanotechnology, University of Mumbai for AFM. Two of the
authors (Azam M. Shaikh and Bharat K. Sharma) is grateful to
University Grants Commission, India for providing Senior
Research Fellowship (UGC-SRF).
N3,N3,N6,N6,N11,N11-Hexakis(4-methoxyphenyl)dibenzo[a,c]-
phenazine-3,6,11-triamine (4). Dark red solid, yield: 161 mg
(67%), mp: 240 1C. FT-IR (KBr, nmax cmꢀ1): 3037.72, 3000.07,
1
2928.33, 1598.68, 1502.71, 1236.60, 1030.52, 824.80; H NMR
(300 MHz, CDCl3): d (ppm) = 8.96 (d, J = 9.0 Hz, 1H), 8.91 (d, J =
9.0 Hz, 1H), 7.93 (d, J = 3.9 Hz, 1H), 7.91 (d, J = 3.9 Hz, 1H), 7.51
(s, 3H), 7.45 (d, J = 2.7Hz, 2H), 7.17 (d, J = 9.0 Hz, 6H), 7.06 (d, J =
9.0 Hz, 6H), 6.88 (d, J = 9.0 Hz, 6H), 6.80 (d, J = 9.0 Hz, 6H), 3.81
(s, 18H); 13C NMR (75 MHz, CDCl3): d (ppm) = 156.66, 156.36,
156.27, 150.20, 149.74, 149.21, 142.38, 140.25, 140.21, 140.10,
139.92, 132.93, 132.14, 129.12, 127.38, 127.13, 127.00, 126.89,
126.47, 124.77, 123.27, 120.34, 119.93, 114.97, 114.72, 113.63,
112.15, 111.82, 55.51, 55.40; HRMS: calcd for C62H52N5O6
[M + H]+ 962.3912; found 962.3932; elemental anal. calcd for
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