Dimethyl Sulfoxide → 5,11-Dioctylindolo[3,2-b]carbazole

HRID 273491

반응식

HRID 273491 반응식
[OH-].[Na+].[CH:3]1[CH:8]=[CH:7][CH:6]=[C:5]2[NH:9][C:10]3[C:11](=[CH:12][C:13]4[NH:14][C:15]5[C:20]([C:21]=4[CH:22]=3)=[CH:19][CH:18]=[CH:17][CH:16]=5)[C:4]=12.Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].CS(C)=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CO>[CH2:24]([N:14]1[C:13]2[C:21](=[CH:22][C:10]3[N:9]([CH2:7][CH2:8][CH2:3][CH2:4][CH2:11][CH2:10][CH2:22][CH3:21])[C:5]4[C:4]([C:11]=3[CH:12]=2)=[CH:3][CH:8]=[CH:7][CH:6]=4)[C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 81401-BromooctaneHCID 14798Sodium HydroxideHCID 958385,11-Dihydroindolo[3,2-b]carbazole

생성물 1

HCID 231320555,11-Dioctylindolo[3,2-b]carbazole수율 180.4%

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 887Methanol용매

실험 절차

A freshly prepared 50% aqueous NaOH solution (4 mL) was added to a well-stirred mixture of 5,11-dihydridoindolo[3,2-b]carbazole, (0.513 g, 2 mmol), benzyltriethylammonium chloride (0.09 g, 0.4 mmol), 1-bromooctane (1.55 g, 8 mmol), and DMSO (20 mL) in a 100-mL flask under an argon atmosphere. The mixture was stirred at room temperature for 2.5 h and then heated to 65° C. and maintained at this temperature for 4 h. Subsequently the reaction mixture was cooled down to room temperature and poured into 200 mL methanol with stirring. The precipitated yellow solid was filtered off and washed with water, and 3 times each with N,N-dimethylformamide, methanol, and acetone. The yellow solid was purified by column chromatography on silica gel using hexane as eluent. Recrystallization from hexane yielded 0.867 g (90.1 %) of 5,11-dioctylindolo[3,2-b]carbazole, (1), which was subject to train sublimation to obtain electrically pure material for OTFT fabrication. DSC showed two endotherms at 84° C. and 101° C. on heating. 1H NMR (CDCl3): δ 8.21 (d, J=7.6 Hz, 2H), 8.01 (s, 2H), 7.47 (dd, J1=7.0 Hz, J2=0.9 Hz, 2H), 7.41 (d, J=7.6 Hz, 2H), 7.21 (dd, J1=7.0 Hz, J2=0.9 Hz, 2H), 4.40 (t, J=7.3 Hz, 4H), 1.95 (pent, J=7.3 Hz, 4H), 1.25-1.50 (m, 20H), 0.86 (m, 6H); IR (NaCl): 3050, 2952, 2921, 2852, 1510, 1469, 1482, 1326, 737 cm−1.

후처리

  1. temperatureheated to 65° C.
  2. temperaturemaintained at this temperature for 4 h
  3. temperatureSubsequently the reaction mixture was cooled down to room temperature
  4. stirringwith stirring
  5. filtrationThe precipitated yellow solid was filtered off
  6. washwashed with water, and 3 times each with N,N-dimethylformamide, methanol, and acetone
  7. customThe yellow solid was purified by column chromatography on silica gel
  8. customRecrystallization from hexane

출처 및 근거

ORD 기록
ord-590580d696b54ccbbaee4d7e36dd5daf
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456424B2

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