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water, and dried with MgSO4. The final product was obtained through
column chromatography (hexane: ethylacetate ¼ 9:1v=v). White solid
product was obtained (Yield: 90%). 1H-NMR (300 MHz in CDCl3):d
8.18 (d, 2H, ArꢁH), 7.47 (d, 2H, ArꢁH), 7.36 (d, 2H, ArꢁH), 7.16 (d,
2H, ArꢁH), 7.08 (d, 2H, ArꢁH), 3.94 (d, 2H, ꢁOꢁCH2ꢁ), 1.77 (m,
1H, ꢁCHꢁ), 1.26 ꢂ 1.57 (m, 8H, ꢁCH2ꢁ), 0.91 (m, 6H, ꢁCH3);
13CꢁNMR (300 MHz in CDCl3): 159.1, 140.3, 129.2, 128.9, 128.3,
123.6, 123.1, 115.7, 112.7, 111.5, 70.8, 39.3, 30.5, 29.1, 23.8, 23.1,
14.1, 11.1.
N-(4-aminophenyl)carbazole (Monomer 2). First, a mixture of
4-iodonitrobenzene (20 mmole), carbazole (15.24 mmmol) and K3PO4
(42 mmol) were added to 1,4-dioxane (100 ml) at room temperature.
After stirring for 30 minutes, CuI (0.4 mmol) and trans-1,2-cyclohexa-
nediamine (2.4 mmol) were added to the mixture. The reaction mix-
ture was refluxed for 24 hours. After cooling the mixture to room
temperature, the dissolved materials were filtered. 1,4-Dioxane was
evaporated, and ethyl acetate was added. The mixture was washed
with distilled water, and dried with MgSO4. The final product was
obtained through column chromatography (hexane: ethylacetate ¼
1
9:1 v=v) with the yield of 98%. H-NMR (300MHz in CDCl3): d 8.58 (d,
1H, ArꢁH), 8.55 (d, 1H, ArꢁH), 8.26 (m, 1H, ARꢁH), 8.23 (m, 1H,
ArꢁH), 8.01 (d, 1H, ArꢁH), 7.98 (d, 1H, ArꢁH), 7.60 (t, 1H, ArꢁH),
7.58 (t, 1H, ArꢁH), 7.51 ꢂ 7.45 (m, 2H, ArꢁH), 7.39 ꢂ 7.33 (m, 2H,
ArꢁH); 13C-NMR (300 MHz in CDCl3): d 144.35, 140.70, 131.85,
127.94, 127.34, 126.36, 124.82, 121.91, 121.33, 110.65; GC-MS m=z ¼ 288
288 (mþ).
In the second step, a mixture of N-(4-nitrophenyl)carbazole
(5 mmol), SnCl2 (30.4 mmol) and EtOH (15 ml) was heated at 70ꢀC
for 4 h. After the mixture was cooled to room temperature, 1 M NaOH
solution was added until the mixture became alkaline. After extraction
with ethyl acetate, the combined organic layers was washed with
brine, dried with MgSO4 and evaporated. The final compound was
1
obtained with the yield of 98%. H-NMR (300 MHz in CDCl3):d 8.15
(d, 1H, ArꢁH), 8.12 (d, 1H, ArꢁH), 7.42 ꢂ 7.22 (m, 8H, ArꢁH), 6.87
(d, 1H, ArꢁH), 6.84 (d, 1H, ArꢁH), 3.81 (s, 2H, ArꢁNH2); 13CꢁNMR
(300 MHz in CDCl3):d 145.89, 141.45, 128.48, 125.70, 122.92, 120.16,
119.39, 115.89, 109.75; GC-MS m=z ¼ 258 (mþ).
Device Fabrication
ITO coated glass was cut into 5.0 cm ꢃ 5.0 cm, and electrode area was
prepared by photo-etching technique. It was sequentially cleaned in an