Journal of Materials Chemistry C
Paper
and the residue was puried by ash column chromatography
4-(4-(14-Phenyldibenzo[a,c]phenazin-9(14H)-yl)phenyl)-4H-
1
(
(
petroleum ether : dichloromethane ¼ 10 : 1) and recrystallized thieno[3,2-b]indole (f). White powder: yield: 0.42 g (42%). H
methylbenzene) to give pure product. White powder; yield: 0.44 NMR (400 MHz, CDCl ) d: 8.80 (dd, J ¼ 8.0, 4.4 Hz, 2H), 8.31
3
1
g (65%); H NMR (400 MHz, CDCl ) d: 8.74 (d, J ¼ 8.0 Hz, 2H), (dd, J ¼ 8.0, 1.2 Hz, 1H), 8.20 (dd, J ¼ 8.1, 0.8 Hz, 1H), 7.89–7.79
3
8
.13 (t, J ¼ 7.2 Hz, 2H), 7.76 (s, 2H), 7.64 (s, 2H), 7.54 (d, J ¼ 5.7 (m, 2H), 7.79–7.67 (m, 4H), 7.60 (t, J ¼ 7.6 Hz, 1H), 7.47–7.39
Hz, 2H), 7.35 (s, 2H), 7.30 (d, J ¼ 8.5 Hz, 2H), 7.22 (t, J ¼ 7.8 Hz, (m, 2H), 7.32–7.29 (m, 2H), 7.24–7.14 (m, 4H), 7.10–6.99 (m,
1
3
13
6
H), 7.14–6.94 (m, 15H), 6.78 (s, 1H). C NMR (100 MHz, 6H), 6.90 (d, J ¼ 5.2 Hz, 1H), 6.84 (t, J ¼ 7.0 Hz, 1H). C NMR
CDCl ) d 147.75, 147.67, 146.67, 146.46, 144.80, 144.69, 138.12, (100 MHz, CDCl ) d 147.68, 147.12, 145.53, 145.27, 144.85,
3
3
1
1
1
1
6
37.92, 134.80, 133.11, 129.93, 129.46, 129.40, 129.23, 129.08, 141.54, 138.93, 138.37, 131.60, 130.02, 129.92, 129.57, 129.50,
28.84, 128.27, 127.38, 127.30, 127.07, 127.03, 126.89, 126.56, 129.09, 128.81, 128.28, 127.81, 127.64, 127.30, 127.15, 126.82,
25.44, 125.42, 125.34, 124.64, 124.19, 123.07, 122.71, 121.16, 126.77, 126.61, 125.96, 125.71, 125.63, 125.35, 124.71, 124.40,
+
17.00, 116.88. HRMS (ESI, m/z): [M + H] calcd for C H N , 123.20, 123.12, 122.71, 122.01, 121.32, 119.87, 118.83, 117.17,
5
0
36 3
+
78.2909; found, 678.2969.
117.06, 117.04, 111.40, 111.03. HRMS (ESI, m/z): [M + H] calcd
N-Phenyl-N-(4-(14-phenyldibenzo[a,c]phenazin-9(14H)-yl) for C H N S, 606.2004; found, 606.2009.
4
2
28 3
0
0
phenyl)naphthalen-1-amine (c). White powder yield: 0.4 g
9-(4 -(9H-Carbazol-9-yl)-[1,1 -biphenyl]-4 yl)-14-phenyl-9,14-
1
(62%). H NMR (400 MHz, CDCl
3
) d: 8.70 (d, J ¼ 8.2 Hz, 2H), 8.20 dihydrodibenzo[a,c]phenazine (g). White powder, yield: 0.52 g
1
(
d, J ¼ 8.1 Hz, 1H), 8.14 (d, J ¼ 7.9 Hz, 1H), 7.81 (s, 1H), 7.79 (d, J (77%). H NMR (400 MHz, CDCl ) d 8.77 (dd, J ¼ 8.2, 3.2 Hz, 2H),
3
¼
2.7 Hz, 1H), 7.71 (d, J ¼ 6.8 Hz, 1H), 7.65 (dd, J ¼ 13.0, 8.0 Hz, 8.18 (d, J ¼ 7.4 Hz, 1H), 8.13 (dd, J ¼ 7.5, 4.3 Hz, 3H), 7.84–7.76
4
H), 7.54 (dd, J ¼ 15.3, 7.6 Hz, 2H), 7.42–7.38 (m, 1H), 7.36 (d, J (m, 2H), 7.69–7.49 (m, 8H), 7.38 (dt, J ¼ 8.9, 7.2 Hz, 8H), 7.29–
1
3
¼
8.0 Hz, 1H), 7.28 (d, J ¼ 5.8 Hz, 2H), 7.24 (s, 1H), 7.13 (d, J ¼ 7.26 (m, 2H), 7.05 (m, 6H), 6.80 (m, 1H). C NMR (100 MHz,
6
.8 Hz, 1H), 7.08–6.99 (m, 4H), 6.92 (d, J ¼ 8.1 Hz, 2H), 6.82 (dd, CDCl ) d: 147.56, 147.33, 145.00, 144.48, 140.88, 140.85, 139.75,
3
1
3
J ¼ 17.0, 8.4 Hz, 4H), 6.74 (dd, J ¼ 16.4, 7.6 Hz, 4H). C NMR 138.37, 137.80, 136.03, 132.40, 129.99, 129.92, 129.42, 129.37,
100 MHz, CDCl ) d 139.84, 129.01, 128.91, 128.72, 127.82, 128.85, 127.68, 127.49, 127.40, 127.35, 127.23, 127.09, 127.04,
26.65, 126.46, 126.37, 126.32, 126.19, 126.06, 125.62, 124.86, 126.65, 126.62, 125.90, 125.62, 125.42, 124.68, 124.57, 123.33,
24.60, 124.39, 123.65, 123.54, 122.29, 122.09, 120.19, 119.24, 123.12, 123.07, 121.22, 120.27, 119.85, 116.96, 116.66, 109.83.
(
3
1
1
1
+
+
18.82, 115.92, 115.63, 108.80. HRMS (ESI, m/z): [M + H] calcd HRMS (ESI, m/z): [M + H] calcd for C H N , 676.2753; found,
50 34 3
for C H N , 652.2753; found, 652.2750.
676.2755.
9-Phenyl-14-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9,14-dihy-
4
8
34 3
0
N-Phenyl-N-(4 -(14-phenyldibenzo[a,c]phenazin-9(14H)-yl)-
0
[
1,1 -biphenyl]-4-yl)naphthalen-1-amine (d). White powder; drodibenzo[a,c]phenazine (h). White powder, yield: 0.56 g
1
1
yield: 0.57 g (78%). H NMR (400 MHz, CDCl
3
) d: 8.77 (d, J ¼ 8.2 (83%). H NMR (400 MHz, CDCl ) d: 8.79 (d, J ¼ 8.3 Hz, 2H), 8.22
3
Hz, 2H), 8.18–8.11 (m, 2H), 7.93 (d, J ¼ 8.5 Hz, 1H), 7.89 (d, J ¼ (d, J ¼ 7.8 Hz, 2H), 8.15 (dd, J ¼ 14.1, 7.9 Hz, 2H), 7.84 (dd, J ¼
8
7
7
6
.0 Hz, 1H), 7.78 (dd, J ¼ 8.6, 6.0 Hz, 3H), 7.67 (t, J ¼ 7.6 Hz, 2H), 6.8, 2.4 Hz, 1H), 7.81 (dd, J ¼ 6.2, 3.0 Hz, 1H), 7.72–7.66 (m, 2H),
.60–7.54 (m, 2H), 7.48 (d, J ¼ 7.4 Hz, 1H), 7.46–7.43 (m, 1H), 7.61 (dt, J ¼ 13.5, 4.7 Hz, 6H), 7.54–7.46 (m, 2H), 7.45–7.35 (m,
.39–7.31 (m, 4H), 7.30–7.30 (m, 3H), 7.25–7.17 (m, 4H), 7.08– 7H), 7.30 (d, J ¼ 3.1 Hz, 1H), 7.14 (d, J ¼ 8.7 Hz, 2H), 7.11–7.03
1
3
13
.96 (m, 10H), 6.94 (t, J ¼ 7.3 Hz, 1H), 6.80 (t, J ¼ 6.5 Hz, 1H).
C
3
(m, 4H), 6.83 (m, 1H). C NMR (100 MHz, CDCl ) d 147.72,
NMR (100 MHz, CDCl ) d 148.34, 147.68, 147.11, 146.53, 144.76, 146.44, 144.79, 144.66, 141.23, 139.94, 137.98, 137.96, 137.69,
3
1
1
1
1
44.71, 143.45, 138.06, 137.94, 137.91, 135.26, 133.73, 133.20, 134.68, 132.96, 129.93, 129.90, 129.85, 129.46, 129.42, 129.04,
31.23, 129.90, 129.69, 129.45, 129.39, 129.09, 129.07, 128.81, 128.83, 128.23, 128.06, 127.50, 127.39, 127.35, 127.15, 127.01,
28.38, 128.26, 127.36, 127.24, 127.22, 127.00, 126.93, 126.77, 126.97, 126.51, 126.48, 125.97, 125.39, 125.32, 124.99, 124.67,
26.52, 126.46, 126.41, 126.36, 126.14, 125.39, 125.33, 124.62, 124.61, 123.75, 123.45, 123.03, 123.02, 121.08, 120.28, 119.91,
24.61, 124.27, 123.03, 121.91, 121.86, 121.66, 121.13, 120.29, 118.07, 117.36, 116.82, 109.85, 109.82. HRMS (ESI, m/z): [M +
1
+
+
117.04, 116.84, 115.29, 113.62. HRMS (ESI, m/z): [M + H] calcd H] calcd for C H N , 676.2753; found, 676.2756.
50 34 3
0
0
for C H N , 728.3066; found, 728.3063.
9-Phenyl-14-(4 -(1-phenyl-1H-benzo[d]imidazol-2-yl)-[1,1 -
(i).
a,c]phenazine (e). White powder; yield: 0.28 g (47%); H NMR Yellow powder, yield: 0.25 g (35.7%). H NMR (400 MHz, CDCl )
5
4
38 3
9
-(4-(9H-Carbazol-9-yl)phenyl)-14-phenyl-9,14-dihydrodibenzo biphenyl]-4-yl)-9,14-dihydrodibenzo[a,c]phenazine
1
1
[
3
(
(
400 MHz, CDCl
3
) d: 8.84–8.77 (m, 2H), 8.39–8.34 (m, 1H), 8.21 d: 8.78 (d, J ¼ 8.3 Hz, 2H), 8.13 (dd, J ¼ 8.0, 3.8 Hz, 2H), 7.89 (d, J
d, J ¼ 8.1 Hz, 1H), 8.10 (d, J ¼ 7.6 Hz, 2H), 7.84 (ddd, J ¼ 9.4, 7.0, ¼ 7.9 Hz, 1H), 7.83–7.77 (m, 2H), 7.69 (t, J ¼ 7.6 Hz, 2H), 7.57
4
1
2
2
1
1
1
1
1
.3 Hz, 2H), 7.73 (dt, J ¼ 17.3, 8.5 Hz, 3H), 7.61 (t, J ¼ 7.6 Hz, (dd, J ¼ 15.7, 8.0 Hz, 4H), 7.48 (dd, J ¼ 16.2, 7.4 Hz, 3H), 7.44–
H), 7.46–7.41 (m, 2H), 7.35 (t, J ¼ 7.7 Hz, 2H), 7.23 (t, J ¼ 7.5 Hz, 7.32 (m, 7H), 7.30 (d, J ¼ 5.5 Hz, 2H), 7.25 (d, J ¼ 7.5 Hz, 2H),
1
3
H), 7.16–7.10 (m, 4H), 7.10–7.04 (m, 4H). 7.01 (d, J ¼ 7.8 Hz, 7.11–6.98 (m, 6H), 6.80 (t, J ¼ 6.6 Hz, 1H). C NMR (100 MHz,
1
3
H), 6.86 (t, J ¼ 7.2 Hz, 1H). C NMR (100 MHz, CDCl ) d CDCl ) d 152.27, 149.28, 147.51, 147.29, 144.89, 144.40, 143.07,
3
3
47.88, 147.72, 145.76, 144.96, 141.22, 139.17, 138.62, 130.10, 141.37, 139.81, 138.29, 137.90, 137.71, 137.31, 137.11, 132.14,
30.04, 129.90, 129.69, 129.54, 128.81, 128.01, 127.72, 127.62, 129.97, 129.89, 129.75, 129.71, 129.39, 129.26, 129.10, 129.06,
27.36, 127.16, 126.86, 126.81, 126.07, 125.68, 124.72, 124.39, 128.83, 128.54, 128.25, 127.88, 127.46, 127.42, 127.27, 127.05,
23.20, 123.13, 122.98, 121.30, 120.15, 119.49, 117.08, 116.96, 127.02, 126.63, 126.60, 126.03, 125.58, 125.40, 125.32, 124.66,
09.80. HRMS (ESI, m/z): [M + H] calcd for C44
+
H
30
N
3
, 600.2440; 124.53, 123.23, 123.09, 123.05, 122.95, 121.16, 119.76, 116.80,
found, 600.2443.
9864 | J. Mater. Chem. C, 2014, 2, 9858–9865
This journal is © The Royal Society of Chemistry 2014