JP2013126955A - 液晶性化合物及び電解質材料 - Google Patents
液晶性化合物及び電解質材料 Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 105
- 239000007788 liquid Substances 0.000 title claims abstract description 67
- 239000002001 electrolyte material Substances 0.000 title claims abstract description 20
- 230000000704 physical effect Effects 0.000 claims abstract description 9
- 239000004973 liquid crystal related substance Substances 0.000 claims description 48
- 230000008859 change Effects 0.000 claims description 20
- 230000007704 transition Effects 0.000 claims description 8
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 150000002500 ions Chemical class 0.000 description 27
- 239000012071 phase Substances 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 13
- 239000002243 precursor Substances 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- 150000001450 anions Chemical class 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 8
- 229910001416 lithium ion Inorganic materials 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 239000003990 capacitor Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- 230000007423 decrease Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 229920001197 polyacetylene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012795 verification Methods 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000002847 impedance measurement Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000004736 wide-angle X-ray diffraction Methods 0.000 description 1
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- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
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Abstract
【解決手段】液晶性化合物では、アンモニウム基とアルコキシフェニル基とを連結したカラムナー液晶相でなり、温度変化に応じて構造変化が生じ、イオン伝導性とイオン非伝導性とに物性が切り替わり、スイッチング機能を発現し得る。
【選択図】図1
Description
R1=R2=R3=O(CH2)n-1CH3、又はO(CH2)q-1(CF2)p-1CF3、
R1=R3=O(CH2)n-1CH3、又はO(CH2)q-1(CF2)p-1CF3、R2=H、
R1=R2=O(CH2)n-1CH3、又はO(CH2)q-1(CF2)p-1CF3、R3=H
のうちいずれかであり、
K,l,m=1〜18、n=6〜18、q=1〜5、p=6〜18であり、
X-は、BF4 -,PF6 -,CF3SO3 -,(CF3SO2)2N-,CH3SO3 -,CH3COO-,CF3COO-,ClO4 -,Br-,I-,Cl-,F-のうちいずれかであることを特徴とする液晶性化合物である。
本発明による液晶性化合物は、アンモニウム基とアルコキシフェニル基とを連結したカラムナー(柱状:Col)液晶相でなり、温度変化によってその構造が変化してイオン伝導特性が変化し得る。具体的に本発明の液晶性化合物は下記一般式で表される。
(2−1)実施例1の液晶性化合物
ここで、下記一般式により表される液晶性化合物は、上述した化3の一般式で表した液晶性化合物の一例を示している。
また、下記一般式により表される液晶性化合物も、上述した化3の一般式で表した液晶性化合物の一例である。
次に、上述した実施例1及び実施例2の各液晶性化合物の合成スキームについて説明する。これら実施例1及び実施例2の液晶性化合物は、図1に示す合成スキームにより合成することができる。なお、ここでは実施例1及び実施例2の液晶性化合物の概略的な合成スキームについて説明し、詳細な合成スキームについては、後の「(5)液晶性化合物の合成」にて後述する。
Information Observed in Dendronized Polyacetylenes”,Journal
of the American Chemical Society,2006,128,16365-16372」に従って合成できる。
以上の構成によれば、この液晶性化合物では、上記の化3で表される一般式により形成されていることにより、温度変化に応じて構造変化が生じ、イオン伝導性とイオン非伝導性とに物性が切り替わるスイッチング機能を発現し得る。
次に、図1に示した合成スキームに従って上述した実施例1及び実施例2の各液晶性化合物を合成し、これら実施例1及び実施例2の各液晶性化合物について各種検証を行った。ここでは、図1に示すように、一般式(4)で表した前駆体を合成した後、この前駆体を用いて実施例1及び実施例2の各液晶性化合物をそれぞれ合成した。
先ず初めに、実施例1及び実施例2の各液晶性化合物の合成に用いる前駆体を、一般式(3)で表す化合物を用いて合成した。出発原料たる一般式(3)の化合物は、文献「V. Percec, E. Aqad, M. Peterca, J. G. Rudick, L. Lemon, J. C. Ronda,B.B.De,
P.A.Heiney,and E.W.Meijer,“Steric Communication
of Chiral Information Observed in Dendronized Polyacetylenes”,Journal of the American Chemical Society, 2006, 128, 16365-16372」に従って合成した。
次に、前駆体から上述した実施例1の液晶性化合物を合成する。この場合、前駆体(0.47[g],0.58[mmol])のメタノール溶液(30[mL])に、AgBF4(0.34[g],1.76[mmol])のメタノール溶液(10[mL])を滴下し、25[℃]で3時間撹拌して反応溶液を生成した。
Hz,2H; CH2),3.66(s,9H;CH3),1.84(m,4H;CH2),1.80(m,2H;CH2),1.46(m,6H;CH2),1.26(m,48H;CH2),0.88(t,J=6.8,9H;CH3);13C NMR(100 MHz,CDCl3,δ):153.93,141.98,139.48,98.32,73.64,70.03,57.31,31.91,30.25,29.74,29.72,29.68,29.66,24.64,29.55,29.42,29.37,29.28,26.05,26.02,22.68,14.10;MS(MALDI-TOF):[M-BF4]+calcd.for C45H86NO3,688.661;found,688.165;Elemental analysis calcd. for C45H86BF4NO3:C 69.65, H 11.17, N 1.81;found:C 69.49, H 11.21, N2.05。
次に、前駆体から上述した実施例2の液晶性化合物を合成する。この場合、前駆体(0.53[g],0.66[mmol])のメタノール溶液(30[mL])に、AgPF6(0.50[g],1.98[mmol])のメタノール溶液(10[mL])を滴下し、25[℃]で3時間撹拌して反応溶液を生成した。
次に、これら実施例1及び実施例2の各液晶性化合物について、熱相転移挙動を示差走査熱量測定・偏光顕微鏡観察により調べた。その結果、実施例1の液晶性化合物は、結晶相が44[℃]でレクタンギュラーカラムナー相となり、141[℃]でヘキサゴナルカラムナー相となり、さらに196[℃]で液体相になった。また、実施例2の液晶性化合物は、結晶相が54[℃]でレクタンギュラーカラムナー相となり、122[℃]でヘキサゴナルカラムナー相となり、さらに168[℃]で液体相となった。なお、実施例1及び実施例2の液晶性化合物の液晶構造の同定は、広角X線回折測定により行なった。
Claims (5)
- 下記一般式
式中のR1、R2及びR3が、
R1=R2=R3=O(CH2)n-1CH3、又はO(CH2)q-1(CF2)p-1CF3、
R1=R3=O(CH2)n-1CH3、又はO(CH2)q-1(CF2)p-1CF3、R2=H、
R1=R2=O(CH2)n-1CH3、又はO(CH2)q-1(CF2)p-1CF3、R3=H
のうちいずれかであり、
K,l,m=1〜18、
n=6〜18、
q=1〜5、
p=6〜18であり、
X-は、BF4 -,PF6 -,CF3SO3 -,(CF3SO2)2N-,CH3SO3 -,CH3COO-,CF3COO-,ClO4 -,Br-,I-,Cl-,F-のうちいずれかである
ことを特徴とする液晶性化合物。 - 温度を上げることによって液晶相が、イオン非伝導性のレクタンギュラーカラムナー相からイオン伝導性のヘキサゴナルカラムナー相に相転移する
ことを特徴とする請求項1記載の液晶性化合物。 - 温度を下げることによって液晶相が、イオン伝導性のヘキサゴナルカラムナー相からイオン非伝導性のレクタンギュラーカラムナー相に相転移する
ことを特徴とする請求項1記載の液晶性化合物。 - 前記ヘキサゴナルカラムナー相のときイオン伝導度が10-4[Scm-1]以上に到達し、
前記レクタンギュラーカラムナー相のときイオン伝導度が10-8[Scm-1]以下に到達する
ことを特徴とする請求項2又は3記載の液晶性化合物。 - 請求項1〜4のうちいずれか1項記載の液晶性化合物を含有しており、温度変化によって前記液晶性化合物の液晶相が相転移し、イオン伝導性からイオン非伝導性、又はイオン非伝導性からイオン伝導性へと物性が切り替わる
ことを特徴とする電解質材料。
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US14/365,149 US8946480B2 (en) | 2011-12-16 | 2012-12-13 | Liquid crystalline compound and electrolyte material |
EP12857955.4A EP2792671B1 (en) | 2011-12-16 | 2012-12-13 | Liquid crystalline compound and electrolyte material |
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Citations (6)
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JP2001338689A (ja) * | 2000-05-30 | 2001-12-07 | Canon Inc | 液晶電解質および二次電池 |
JP2001351435A (ja) * | 2000-06-09 | 2001-12-21 | Canon Inc | 電解質および二次電池 |
JP2008037823A (ja) * | 2006-08-09 | 2008-02-21 | Univ Of Tokyo | イオン伝導体、化合物又はその塩、双連続キュービック液晶、電気化学デバイス |
JP2010060973A (ja) * | 2008-09-05 | 2010-03-18 | Univ Of Tokyo | 液晶セル |
WO2010092897A1 (ja) * | 2009-02-16 | 2010-08-19 | コニカミノルタホールディングス株式会社 | 電解質組成物、および二次電池 |
JP2011192611A (ja) * | 2010-03-16 | 2011-09-29 | Sekisui Chem Co Ltd | 固液ハイブリッド電解質層 |
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2011
- 2011-12-16 JP JP2011276146A patent/JP5592869B2/ja not_active Expired - Fee Related
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2012
- 2012-12-13 US US14/365,149 patent/US8946480B2/en not_active Expired - Fee Related
- 2012-12-13 EP EP12857955.4A patent/EP2792671B1/en not_active Not-in-force
- 2012-12-13 WO PCT/JP2012/082315 patent/WO2013089174A1/ja active Application Filing
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2001338689A (ja) * | 2000-05-30 | 2001-12-07 | Canon Inc | 液晶電解質および二次電池 |
JP2001351435A (ja) * | 2000-06-09 | 2001-12-21 | Canon Inc | 電解質および二次電池 |
JP2008037823A (ja) * | 2006-08-09 | 2008-02-21 | Univ Of Tokyo | イオン伝導体、化合物又はその塩、双連続キュービック液晶、電気化学デバイス |
JP2010060973A (ja) * | 2008-09-05 | 2010-03-18 | Univ Of Tokyo | 液晶セル |
WO2010092897A1 (ja) * | 2009-02-16 | 2010-08-19 | コニカミノルタホールディングス株式会社 | 電解質組成物、および二次電池 |
JP2011192611A (ja) * | 2010-03-16 | 2011-09-29 | Sekisui Chem Co Ltd | 固液ハイブリッド電解質層 |
Non-Patent Citations (1)
Title |
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JPN6013009393; PERCEC,V. et al.: 'Steric communication of chiral information observed in dendronized polyacetylenes' Journal of the American Chemical Society Vol.128, 2006, p.16365-16372 * |
Also Published As
Publication number | Publication date |
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EP2792671A1 (en) | 2014-10-22 |
EP2792671B1 (en) | 2016-04-13 |
US8946480B2 (en) | 2015-02-03 |
WO2013089174A1 (ja) | 2013-06-20 |
EP2792671A4 (en) | 2015-04-29 |
US20140336414A1 (en) | 2014-11-13 |
JP5592869B2 (ja) | 2014-09-17 |
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