JP6105739B2 - 電気化学エネルギー蓄積用の有機活物質 - Google Patents
電気化学エネルギー蓄積用の有機活物質 Download PDFInfo
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- JP6105739B2 JP6105739B2 JP2015538307A JP2015538307A JP6105739B2 JP 6105739 B2 JP6105739 B2 JP 6105739B2 JP 2015538307 A JP2015538307 A JP 2015538307A JP 2015538307 A JP2015538307 A JP 2015538307A JP 6105739 B2 JP6105739 B2 JP 6105739B2
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Description
(1)良好な電子伝導体であること、
(2)高いエネルギー密度を提供すること、
(3)高い出力密度を提供すること、
(4)標準的なリチウムイオン電解質中に不溶であること。
ここで、
−Redは、酸化還元中心であり;
−Rは、架橋基であり;かつ
−Mは、導電性ポリマーをもたらすモノマーである。
A1.INZ−0の合成
クロロアセトン(8.09g、87.40mmol)を滴状で、2−ブタノン(25mL)中の2−プロパノールピリジン(10.00g、72.89mmol)の溶液に添加した。KI(435mg、2.62mmol)を添加し、混合物を24時間にわたって加熱還流した。混合物を室温まで冷却し、Et2O(100mL)を添加した。溶媒をデカンタし、残留物を500mLのRBFに移した。有機相を4×50mLの水で更に抽出し、水相を集めた。N2雰囲気下で、NaHCO3を撹拌しながら水性混合物にゆっくりと添加し、活発な気体の発生を観測した。混合物を90分にわたって加熱還流し、室温まで冷却した。暗色混合物を5×100mLのEt2Oで抽出した。有機相を集め、塩水(50mL)で洗浄し、Na2SO4で一晩乾燥させ、減圧下で濃縮した。シリカプラグ(溶離液:CH2Cl2/AcOEt 1:1)上での濾過によって残留物を精製した。減圧下での溶媒蒸発の後に、淡黄色のオイルとして生成物を得た(4.200g、23.97mmol、収率33%)。
9(4.100g、23.39mmol)及びクロロベンゼン(220mL)中10%のPt/C(4.56g、2.34mmol)の混合物を、開口500mLの丸底フラスコ内で24時間にわたって室温で撹拌した。混合物を、クロロベンゼンで洗浄しつつ濾過して触媒を除去し、濾過物を減圧下で濃縮した。シリカゲル(溶離液:CH2Cl2/AcOEt 2:3)上でのクロマトグラフィーによって、残留物を精製し、減圧下での溶媒蒸発の後に、透明なオイルを得た。残留物をEt2O(10mL)で粉砕し(triturated)、淡緑色の固体として純生成物を得た(901mg、2.58mmol、収率22%、m.p.:148−150℃)。
N2雰囲気下で、10(350mg、1.004mmol)、4(672mg、2.35mmol)、DCC(515mg、2.49mmol)、及びDMAP(27mg、0.22mmol)の混合物にMeCN(13ml)を添加した。EDOT誘導体4を、本願と共通の発明者を共有し、2011年9月15日に出願された、伊国特許出願第TO2011A000830号明細書に開示されている方法によって得ることができる。混合物を4日間にわたって室温で撹拌し続け、MeCnで洗浄し、濾過した。濾過物を集め、減圧下で濃縮し、シリカゲル(溶離液:CH2Cl2/AcOEt 9:1)上でクロマトグラフィーによって精製した。50℃で減圧下での溶媒蒸発の後に、緑色のオイルとしての生成物を得た(499mg、0.564mmol、収率56%)。
エタノールアミン(4.759g、77.92mmol)を、滴状で、水(60mL)中の1,4,5,8−ナフタレンテトラカルボン酸二無水物(5.226g、19.48mmol)の懸濁液に添加し、混合物を24時間にわたって80℃で加熱した。混合物を室温まで冷却し、水と、それに続いてアセトンで洗浄しつつブフナー漏斗上での濾過によって生成物を集めた。残留溶媒を50℃での減圧下で蒸発させ、淡褐色の固体としての生成物を得た(5.785g、17.73mmol、収率91%、m.p.:325℃(lit.321−323℃))。
試験管中で、11(3.000g、9.20mmol)、グルタル酸無水物(21.6g、184mmol)、及びDMAP(112mg、0.920mmol)の混合物を、30分にわたって110℃で加熱した。混合物を75mLの水に注ぎ、1mLのHCl(aq.)37%を添加して酸性にした。得られた懸濁液を、一晩室温で撹拌し、水と、その後に続いて少量mLのEtOHで洗浄して、ヒルシュ漏斗上で濾過した。生成物をシクロヘキサノンからの結晶化によって精製し、残留溶媒を減圧下で蒸発させた。桃色の固体を得た(3.168g、5.44mmol、収率59%、m.p.:220℃)。
アセトニトリル(35mL)を、12(3.160g、5.42mmol)、EDOT−MeOH(2.33g、13.53mmol)、DCC(2.44mg、11.82mmol)、及びDMAP(89mg、0.74mmol)の混合物に添加した。EDOT−MeOHは、シグマアルドリッチ(製品番号#687553)から入手可能な市販品(ヒドロキシメチルEDOT)である。混合物を、8日間にわたって室温で撹拌しつづけ、MeCNで洗浄して濾過した。濾過物を集め、減圧下で濃縮した。残留物を、シリカゲル(溶離液:CH2Cl2/AcOEt 7:3)上でのクロマトグラフィーによって精製した。溶媒を減圧下で蒸発させ、残留物をEt2Oで粉砕し(triturated)、淡黄色の固体としての生成物を得た(1.304g、1.46mmol、収率27%、m.p.:124−125℃)。
B1.INZ−0の重合
N2雰囲気下で、N−メチル−イミダゾール(1.313g、16.00mmol)及びBaytron−CB−40(21.7g、15.2mmol)を、乾燥MeCN(40mL)中の2−メチルインドリジン(INZ−0、1.000g、7.62mmol)の撹拌溶液に添加した。混合物を7.5時間にわたって加熱還流し、室温まで冷却し、3日間にわたって撹拌し続けた。沈殿物を、暗色固体として濾過によって集めた。生成物を超音波処理し、MeCNで二度、濾過した。同じ手順をMeOH(2×50mL)で繰り返した。生成物を最後に新鮮なMeOHと、その後に続くEt2Oで洗浄し、濾過した。残留溶媒を40℃での減圧下で除去した。暗色固体を得た(1.160g)。
手順A(バッチp−NPBIM−1B)
N2雰囲気下で、無水ベンゾニトリル(5mL)を、シュレンク管内のNPBIM−1(1.000g、1.122mmol)及び無水Fe(OTs)3 (2.979g、5.231mmol)の混合物に添加した。管を密封し、24時間にわたって145℃で加熱した。混合物を室温まで冷却し、セルロース円筒ろ紙に注いだ。無色の抽出物が得られるまで、固体残留物を、ソックスレー抽出器中でMeCNで抽出した。固体を、CHCl3とその後に続くMeOHでさらに抽出した。濾紙内の黒色固体残留物を50℃で12時間にわたって減圧下で乾燥させ、集めた(737mg)。
乾燥CHCl3(20mL)及び無水MeCN(10mL)の混合物中でのNPBIM−1(735 mg、0.835mmol)及び無水Fe(OTs)3(2.189g、3.845mmol)の懸濁液を、N2雰囲気下で14時間にわたって還流した。明るい黄色混合物が、緑色、次いで青に変わる。混合物を室温まで冷却し、セルロース円筒ろ紙に注いだ。無色の抽出物が得られるまで、固体残留物を、ソックスレー抽出器中でCHCl3と、その後に続くMeOHで抽出した。紺青色固体を集め、残留溶媒を65℃での減圧下で除去した(150mg)。
図9のデータは、リチウム電池の構成から得た。水に入れたグラファイト(SFG6、ティムカル社製、26質量%)、カルボキシメチルセルロース(シグマ社製、1%)、及びスチレン−ブタジエンゴム(Targray社製、1%)と一緒に、Poly−NPbIm−1を用いて複合電極(72質量%)を調製した。結果物のスラリーを300μmの湿潤厚さでアルミホイル上にキャストした。電極を、一晩、80℃の雰囲気で乾燥させた。ホイルから、直径16mmの円形電極を、切り取り、コイン型のセルを組み立てるのに用いた。コイン型セル中のカウンター電極は金属リチウムであり、セパレーターはガラス繊維であり、電解質はエチレンカーボネート/ジメチルカーボネートを質量で1:1の中で1MのLiClO4である。コイン型のセルを、BioLogic社製のVMP3充放電機を用いて試験した。
図9は、5つの異なる割合での放電下におけるPoly−NPbIM−1の電力伝達を示している。材料からは、10倍高い電流(C)での放電下において、(C/10での)元容量の70%超の配送を観測した。
図10では、NPbIm−1の長期安定性を示している。材料は、1000サイクルを完了し、元容量の85%超を保持した。
材料のサンプルを、エチレンカーボネート/ジメチルカーボネート混合物中に加え、7日間にわたってマグネチックスターラーにかけた。粉末を濾過し、乾燥させた。質量は変化しなかった。溶媒の変色は観測されなかった。
本発明の実施態様の一部を以下の項目[1]−[10]に記載する。
[項目1]
構造Red−R−Mを含有している化合物であって、
−Redは、酸化還元中心であり;
−Rは、架橋基であり;かつ
−Mは、導電性ポリマーをもたらすモノマーである、
化合物。
[項目2]
前記酸化還元中心が、アリーレンビスイミド類、インドリジン類、ヴィオローゲン類、ヴィオレン類、アントラキノン類からなる群から選択される基を有している、項目1に記載の化合物。
[項目3]
下記の構造で示される、項目1又は2に記載の化合物:
前記モノマーMが、チオフェン、ピロール、パラフェニレンビニレン、フラン、カルバゾール、シロール、フルオレンからなる群から選択される基を有している、項目1〜3のいずれか一項に記載の化合物。
[項目5]
3,4−エチレンジオキシチオフェン(EDOT)基を有している、項目4に記載の化合物。
[項目6]
前記橋Rが、直線状アルキレン鎖若しくは分枝状アルキレン鎖若しくはグリコール鎖、又は下記の中から選択される官能基の組み合わせ:−C(=O)−、−C(=S)−、−O−C(=O)−、−O−C(=S)−、−O−C(=O)−O−、−(C=O)−O−、−C(=S)−O−、−C(=S)−S−、−C(=O)−NR’−若しくは−C(=S)−NR’−(R’はH若しくはアルキル)、−SO、−SO 2 、又は一若しくは複数の前記官能基によって分離されている任意の直線状アルキル鎖若しくは分枝状アルキル鎖若しくはグリコール鎖の組み合わせを、有している、項目1〜5のいずれか一項に記載の化合物。
[項目7]
下記に示す構造を有している、項目1〜6のいずれか一項に記載の化合物:
項目1〜7のいずれか一項に記載の化合物の重合によって得られるポリマー。
[項目9]
電気化学エネルギーを蓄積するための、項目8に記載のポリマーの使用。
[項目10]
リチウムイオン電池での、項目8に記載のポリマーの使用。
Claims (9)
- 構造Red−R−Mを有している化合物であって、
−Redは、酸化還元中心であり;
−Rは、架橋基であり;かつ
−Mは、導電性ポリマーをもたらすペンダント基であり、
前記酸化還元中心が、インドリジンを有し、
前記ペンダントM基が、チオフェン、ピロール、パラフェニレンビニレン、フラン、カルバゾール、シロール、フルオレンからなる群から選択される基を有している、
化合物。 - 3,4−エチレンジオキシチオフェン(EDOT)基を有している、請求項1に記載の化合物。
- 前記架橋基Rが、直線状アルキレン鎖若しくは分枝状アルキレン鎖若しくはグリコール鎖、又は下記の中から選択される官能基の組み合わせを有している、請求項1〜3のいずれか一項に記載の化合物:−C(=O)−、−C(=S)−、−O−C(=O)−、−O−C(=S)−、−O−C(=O)−O−、−(C=O)−O−、−C(=S)−O−、−C(=S)−S−、−C(=O)−NR’−若しくは−C(=S)−NR’−(R’はH若しくはアルキル)、−SO、−SO2、又は一若しくは複数の前記官能基によって分離されている任意の直線状アルキル鎖若しくは分枝状アルキル鎖若しくはグリコール鎖の組み合わせ。
- 請求項1〜5のいずれか一項に記載の化合物の重合によって得られるポリマー。
- 電気化学エネルギーを蓄積するための、請求項6に記載のポリマーの使用。
- リチウムイオン電池での、請求項6に記載のポリマーの使用。
- 構造Red−R−Mを有している化合物の重合によって得られるポリマーを含むリチウムイオン電池であって、
−Redは、酸化還元中心であり;
−Rは、架橋基であり;かつ
−Mは、導電性ポリマーをもたらすペンダント基であり、
前記酸化還元中心が、アリーレンビスイミドを有し、
前記ペンダントM基が、チオフェン、ピロール、パラフェニレンビニレン、フラン、カルバゾール、シロール、フルオレンからなる群から選択される基を有している、
化合物の重合によって得られるポリマーを含むリチウムイオン電池。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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PCT/EP2012/071615 WO2014067574A1 (en) | 2012-10-31 | 2012-10-31 | Organic active materials for electrochemical energy storage |
Publications (2)
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