JP4908882B2 - ベンゾビスアゾール骨格をもつ有機π電子系材料およびその製造方法 - Google Patents
ベンゾビスアゾール骨格をもつ有機π電子系材料およびその製造方法 Download PDFInfo
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- JP4908882B2 JP4908882B2 JP2006065086A JP2006065086A JP4908882B2 JP 4908882 B2 JP4908882 B2 JP 4908882B2 JP 2006065086 A JP2006065086 A JP 2006065086A JP 2006065086 A JP2006065086 A JP 2006065086A JP 4908882 B2 JP4908882 B2 JP 4908882B2
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Description
第二工程: アルキルリチウム、リチウムアルキルアミド、またはリチウム-亜鉛アート錯体を塩基として用いてメタル化した一般式(6)または(7)
第三工程:一般式(8)または(9)を金属触媒存在下、エチニルトリメチルシランと反応させ、一般式(16)または(17)
を合成し、次いで、一般式(16)または(17)をメタノール中、炭酸カリウムと反応させることにより、一般式(11)または(12)
第四工程: 一般式(8)、(9)、(11)または(12)の組み合わせのクロスカップリング反応による工程
このようなベンゾビスアゾール誘導体は、例えば非特許文献1などに示されるジアミノベンゼンジチオール塩酸塩とカルボン酸誘導体との手法を用いて合成することができるが、反応基質が制限される欠点がある。本発明では下図に示すようなクロスカップリング法を用いることにより、より汎用性が高い基質の導入が可能である。
本発明のベンゾビスチアゾール化合物は、理論計算の結果、高い平面性を有することがわかっている。具体的には、n=0である一般式(15)のベンゾビスチアゾール二量体においてAr 1 がフェニレン基、R 1 がブチル基のベンゾビスチアゾール二量体を熱トルエンにて再結晶を行い得られた単結晶、およびAr 1 がフェニレン基、R 1 がジドデシルアミノ基のベンゾビスチアゾール二量体をクロロホルム−エタノールにて再結晶を行い得られた単結晶は、X線結晶構造解析の結果、高い平面性を有することが明らかとなった。
2,6−ジヨードベンゾ[1,2−d:4,5−d’]ビスチアゾール(111 mg, 250
μmol)、Pd2(dba)3・CHCl3 (10.4 mg, 10.0 μmol)、2−ジシクロヘキシルホスフィノ−2’,6’−ジメトキシ−1,1’−ビフェニル(8.2 mg, 20 μmol)、K2CO3 (233 mg, 1.69 mmol)、5−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)−2−トリイソプロピルシリルチオフェン(229 mg, 625 μmol)の混合物にDME (10.0 mL)と水(2.5 mL)を加えて加熱、12時間還流した。室温に冷却し、固体をセライトろ過により除いた。ろ液に水を加えて塩化メチレンで抽出、MgSO4で乾燥、濃縮した。ヘキサンを加え、ろ過により目的物1b (115 mg, 172 μmol)を得た。さらにろ液からシリカゲルカラムクロマトグラフィー(ヘキサン:トルエン=1:1)により目的物1b (10 mg, 15μmol)を得た(合計125 mg, 187 μmol, 75%)。
次に、下式に示すベンゾビスチアゾールの4,8−位のヨウ素化について[実施例8]〜[実施例10]で説明する。
化合物(1a) (223 mg, 213 μmol)のTHF (21.0 mL)懸濁液に、n-ブチルリチウムのヘキサン溶液(1.6 M, 150 μL, 240 μmol)を−78℃で滴下した。懸濁液を−78℃で1時間撹拌した後、赤色溶液になるまでゆっくりと昇温しながら撹拌した。溶液を再び−78℃に冷却し、ヨウ素 (83.4 mg, 329 μmol)のTHF (3.0 mL)溶液を滴下した。−78℃で0.5時間撹拌した後、ゆっくりと室温に昇温した。混合物にNa2SO3水溶液を加え、塩化メチレンで抽出、Na2SO4で乾燥、濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン:CH2Cl2 = 1:1)により原料1a (43.6 mg, 41.6 μmol, 20%回収)、目的物2a (179 mg, 153 μmol, 72%)および目的物3a (20.6 mg, 15.9 μmol, 7%)を得た。
3a:1H NMR (270 MHz, CDCl3): δ0.89 (t, 3JHH = 6.6 Hz, 12H), 1.28 (s, 56H), 1.33 (br, 16H), 1.61 (br, 8H), 3.33 (t, 3JHH = 7.4 Hz, 8H), 6.66 (d, 3JHH = 8.6 Hz, 4H), 7.94 (d, 3JHH = 8.6 Hz, 4H).
化合物(1b) (335 mg, 501 μmol)にTHF (24.0 mL)を加え、−5℃に冷却した。リチウムジイソプロピルアミドのヘキサン/THF溶液(1.00 mmol)を滴下し、−5℃で1時間撹拌した後、−78℃に冷却した。ヨウ素(190 mg, 749 μmol)を加え、撹拌しながらゆっくりと室温に昇温した。混合物にNa2S2O3水溶液を加え、エーテルで抽出、MgSO4で乾燥、濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン:トルエン = 2:1)により原料1b (9.0 mg, 13 μmol, 3%回収),目的物2b (292 mg, 367 μmol, 73%)および目的物3b (56.1 mg, 60.9 μmol, 12%)を得た。
3b:1H NMR (270 MHz, CDCl3): δ 1.15 (d, 3JHH = 7.3 Hz, 36H), 1.40 (sept, 3JHH = 7.3 Hz, 6H), 7.29 (d, 3JHH = 3.6 Hz, 2H), 7.78 (d, 3JHH = 3.6 Hz, 2H). 13C NMR (68 MHz, CDCl3): δ 11.90, 18.66, 78.91, 130.34, 136.37, 140.44, 141.27, 141.86, 149.86, 159.62. LRMS (EI): m/z 920 [M+], 877 [(M−C3H7)+].
化合物(1c) (2.31 g, 5.06 mmol)にTHF (300 mL)を加えた。LitBu2ZnTMPのヘキサン/THF溶液(5.57 mmol)を滴下し、室温で75分撹拌した後、0 ℃に冷却した。ヨウ素 (12.8 g, 50.4 mmol)を加え、撹拌しながらゆっくりと室温に昇温した。混合物にNa2S2O3水溶液を加え、クロロホルムで抽出、Na2SO4で乾燥、濃縮し、シリカゲルカラムクロマトグラフィー(トルエン)により原料1c (230 mg, 504 μmol, 10%rec.)、目的物2c (2.06 g, 3.54 mmol, 70%)を得た。
化合物(1c) (2.46 g, 5.39 mmol)にTHF (300 mL)を加えた。LitBu2ZnTMPのヘキサン/THF溶液(21.6 mmol)を滴下し、室温で75分撹拌した後、−78℃に冷却した。ヨウ素 (27.4 g, 108 mmol)を加え、撹拌しながらゆっくりと室温に昇温した。混合物にNa2S2O3水溶液を加え、クロロホルムで抽出、Na2SO4で乾燥、濃縮し、ジクロロメタンを加え、沈殿物をろ過することにより、目的物3c (3.01 g, 5.17 mmol, 96%)を得た。
次に、アセチレンスペーサーの導入に関して、[実施例11]〜[実施例16]で説明する。
化合物2a (118 mg, 101 μmol),PdCl2(PPh3)2 (3.6 mg, 5.1 μmol)、エチニルトリメチルシラン (20 μL, 142 μmol)、Et3N (450 μL)の混合物をTHF (4.5 mL)に溶解した。CuI (1.1 mg, 5.8 μmol)を加え、室温で15分撹拌した後加熱、12時間還流した。室温に冷却し、水を加えて塩化メチレンで抽出、Na2SO4で乾燥、濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン:CH2Cl2 = 1:1)により目的物4a (102 mg, 88.9 μmol)を得た(88%)。
化合物2b (275 mg, 346 μmol)、PdCl2(PPh3)2 (7.2 mg, 10 μmol)、CuI (3.9 mg, 20 μmol)、THF (15 mL)、Et3N (5.0 mL)の混合物にエチニルトリメチルシラン(70 μL, 495 μmol)を加えた。室温で20分撹拌した後加熱、18時間還流した。室温に冷却し、水を加えてクロロホルムで抽出、MgSO4で乾燥、濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン:トルエン = 2:1)により目的物4b (221 mg, 289 μmol)を得た(84%)。
化合物2c (504 mg, 865 μmol)、PdCl2(PPh3)2 (18.9 mg, 26.9 μmol)、CuI (7.0 mg, 37 μmol)、THF (30 mL)、Et3N (10 mL)の混合物にエチニルトリメチルシラン (190 μL, 1.34 mmol)を0℃で加え加熱、18時間還流した。室温に冷却し、水を加えてジクロロメタンで抽出、Na2SO4で乾燥、濃縮した。粗生成物にヘキサンを加え、沈殿物をろ過し、目的物を得た。さらにろ液を濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン:トルエン = 2:1)により精製し、目的物4cを得た。合計収量451 mg(815 μmol)、収率94%。
1H NMR (270 MHz, CDCl3): δ 0.42 (s, 9H), 0.96 (t, 3JHH = 7.3 Hz, 6H), 1.40 (sext, 3JHH = 7.3 Hz, 4H), 1.66 (m, 4H), 2.70 (t, 3JHH = 7.6 Hz, 4H), 7.33 (d, 3JHH = 7.8 Hz, 4H), 8.04 (d, 3JHH = 7.8 Hz, 2H), 8.08 (d, 3JHH = 7.8 Hz, 2H), 8.46 (s, 1H).
1H NMR (400 MHz, CDCl3): δ 0.88 (t, 3JHH = 6.6 Hz, 12H), 1.27 (s, 56H), 1.33 (br, 16H), 1.60 (br, 8H), 3.33 (t, 3JHH = 7.4 Hz, 8H), 3.82 (s, 1H), 6.66 (d, 3JHH = 9.0 Hz, 2H), 6.67 (d, 3JHH = 9.0 Hz, 2H), 7.93 (d, 3JHH = 9.0 Hz, 2H), 7.99 (d, 3JHH = 9.0 Hz, 2H), 8.32 (s, 1H). LRMS (FAB): m/z 1072 [(M+H)+].
化合物4b (170 mg, 222 μmol)とK2CO3 (4.6 mg, 33 μmol)の混合物にメタノール (1.25 mL)とTHF (2.5 mL)を加え、室温で6時間撹拌した。水を加え、塩化メチレンで抽出、MgSO4で乾燥、濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン:トルエン = 5:3)により目的物5b (150 mg, 216 μmol)を得た(97%)。
化合物4c (442 mg, 800 μmol)とK2CO3 (10.7 mg, 77.4 μmol)の混合物にメタノール (20 mL)とTHF (80 mL)を加え、室温で11時間撹拌した。塩化アンモニウム水を加え、ジクロロメタンで抽出、Na2SO4で乾燥、濃縮し、目的物5c (363 mg, 623μmol)を得た(76%)。
次に、アセチレン架橋ベンゾビスチアゾール二量体の合成に関して、[実施例17]〜[実施例19]で説明する。
化合物2a (128 mg, 109 μmol)、Pd(PPh3)4 (6.6 mg, 5.7 μmol)、化合物5a (127 mg, 119 μmol)、Et3N (500 μL)の混合物をTHF (5.0 mL)に溶解した。CuI (1.5 mg, 7.9 μmol)を加え、室温で15分撹拌した後加熱、11時間還流した。室温に冷却し、水を加えてクロロホルムで抽出、Na2SO4で乾燥、濃縮した。シリカゲルカラムクロマトグラフィー(ヘキサン:クロロホルム = 3:4)で分離し、さらにPTLC (ヘキサン:クロロホルム = 2:5)により精製を行い目的物6a (81.3 mg, 38.4 μmol)を得た(35%)。
化合物2b (159 mg, 200 μmol)、化合物5b (138 mg, 199 μmol)、Pd(PPh3)4 (6.9 mg, 6.0 μmol)、 CuI (2.3 mg, 12 μmol)の混合物にTHF (10.0 mL)とEt3N (3.3 mL)を加えた。室温で10分撹拌した後加熱、24時間還流した。室温に冷却し、溶媒を留去して塩化メチレンを加え、セライトろ過により不溶物を取り除いた。ろ液に水を加えて塩化メチレンで抽出、MgSO4で乾燥、濃縮した。シリカゲルカラムクロマトグラフィー(ヘキサン:トルエン = 1:1)により精製を行い目的物6b (110 mg, 80.9 μmol)を得た(41%)。
化合物2c (36.1 mg, 75.1 μmol)、化合物5c (44.7 mg, 76.7 μmol)、Pd(PPh3)4 (4.6 mg, 4.0 μmol)、 CuI (1.4 mg, 7.4 μmol)の混合物にTHF:Et3N = 3:1溶液(5 mL)を加えた。室温で5時間撹拌した後加熱、7時間還流した。室温に冷却し、塩化アンモニウム水を加え、不溶物を採取し、トルエン、エタノール、クロロホルムの順に洗浄し、目的物6c (37.7 mg, 40.3 μmol)を得た(54%)。
化合物6bおよび6cについてはX線結晶構造解析によりその構造を明らかにした。[実施例20]および[実施例21]でその結果を示す。
次に、アセチレン架橋ベンゾビスチアゾール三量体の合成について、[実施例23]〜[実施例25]で示す。
化合物3a (45.4 mg, 34.9 μmol)、Pd(PPh3)4 (2.1 mg, 1.8 μmol)、化合物5a (80.2 mg, 74.8 μmol)、Et3N (320 μL)の混合物をTHF (3.2 mL)に溶解した。CuI (1.4 mg, 7.4 μmol)を加え、室温で15分撹拌した後加熱、11時間還流した。室温に冷却し、水を加えてクロロホルムで抽出、Na2SO4で乾燥、濃縮した。シリカゲルカラムクロマトグラフィー(ヘキサン:クロロホルム = 2:3)で分離し、さらにGPC-HPLC (LC-918, CHCl3)により精製を行い目的物8a (41.7 mg, 13.1 μmol)を得た(38%)。
化合物3b (99.8 mg, 108 μmol)、Pd(PPh3)4 (6.3 mg, 5.5 μmol)、CuI (2.1 mg, 11 μmol)、THF (10 mL)、Et3N (3.3 mL)の混合物に、化合物5b (150 mg, 216 μmol)のTHF (3 mL)溶液を加えた.室温で20分撹拌した後加熱、7時間還流した。室温に冷却し、溶媒を留去しクロロホルムを加え、セライトろ過により不溶物を取り除いた。ろ液を濃縮し、ヘキサンを加えてろ過、エーテル、水で洗浄し目的物8b (82.1 mg, 40.0 μmol)を得た(37%)。
化合物3c (71.0 mg, 100 μmol)、Pd(PPh3)4 (5.7 mg, 4.9 μmol)、CuI (2.2 mg, 12 μmol)、の混合物に、化合物5c (98.9 mg, 206 μmol)のTHF:Et3N = 3:1溶液(20 mL)を加え加熱、6時間還流した。室温に冷却し、沈殿物をろ過により採取し、塩化アンモニア水、水、エタノール、クロロホルムの順に洗浄し目的物8c (88.7 mg, 63 μmol)を得た(63%)。
Claims (6)
- 一般式(1)で表されるベンゾビスアゾール骨格を有する電子材料用π共役有機化合物。
- 以下の4工程を有する請求項1乃至5の何れかに記載の電子材料用π共役有機化合物の製造方法。
第一工程: 一般式(3)
第二工程:アルキルリチウム、リチウムアルキルアミド、またはリチウム−亜鉛アート錯体を塩基として用いてメタル化した一般式(6)または(7)
第三工程:
一般式(8)または(9)を、金属触媒存在下、エチニルトリメチルシランと反応させ、一般式(16)または(17)
を合成し、次いで、一般式(16)または(17)をメタノール中、炭酸カリウムと反応させることにより、一般式(11)または(12)
第4工程:一般式(8)、(9)、(11)または(12)の組み合わせのクロスカップリング反応による工程
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