JP2005075922A - フッ素イオン検出用重合体及び重合体の製造方法 - Google Patents
フッ素イオン検出用重合体及び重合体の製造方法 Download PDFInfo
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- 238000004519 manufacturing process Methods 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 17
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 title abstract description 40
- 238000001514 detection method Methods 0.000 title abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 37
- -1 fluorine ions Chemical class 0.000 claims description 78
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- DRCPBHLBJBZQBG-UHFFFAOYSA-N bis(4-ethynylphenyl)-dimethylsilane Chemical compound C=1C=C(C#C)C=CC=1[Si](C)(C)C1=CC=C(C#C)C=C1 DRCPBHLBJBZQBG-UHFFFAOYSA-N 0.000 description 5
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- MSPAOVIUWZYDOL-UHFFFAOYSA-N C=1C=C(C#C)C=CC=1[Si](CCCCCC)(CCCCCC)C1=CC=C(C#C)C=C1 Chemical compound C=1C=C(C#C)C=CC=1[Si](CCCCCC)(CCCCCC)C1=CC=C(C#C)C=C1 MSPAOVIUWZYDOL-UHFFFAOYSA-N 0.000 description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- IWZPSIAFOJCGIM-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1-c1ccc(C)cc1 Chemical compound CC(C)(C)c(cc1)ccc1-c1ccc(C)cc1 IWZPSIAFOJCGIM-UHFFFAOYSA-N 0.000 description 1
- RZTDESRVPFKCBH-UHFFFAOYSA-N Cc(cc1)ccc1-c1ccc(C)cc1 Chemical compound Cc(cc1)ccc1-c1ccc(C)cc1 RZTDESRVPFKCBH-UHFFFAOYSA-N 0.000 description 1
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- 238000013461 design Methods 0.000 description 1
- NRAYZPGATNMOSB-UHFFFAOYSA-N dichloro(dihexyl)silane Chemical compound CCCCCC[Si](Cl)(Cl)CCCCCC NRAYZPGATNMOSB-UHFFFAOYSA-N 0.000 description 1
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 1
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- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 1
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- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
Description
で示されることを特徴としている。
で示されることを特徴としている。
で表される単量体と、パラジウムを含む第1の触媒と、銅を含む第2の触媒と、を含む混合物を重合させる工程を含むことを特徴としている。
で表される第1の単量体と、一般式(5);
まず、フッ素イオン源としてのTBAFを、実施例1の重合体を含むTHF内に滴定することより、実施例1の重合体のUV可視光吸収の変化を調査した。具体的には、TBAFが、0,20,40,60,80,100,120,140,160×10-4Mとなった時点での実施例1の重合体の波長約270nmから500nmまでの光の吸収スペクトルをJASCO UV−550を用いて測定した。
この新しいICT複合体の存在の決定的な証拠を得るために、我々は、TBAFを添加して、NMRスペクトルを決定した。これによると、図4に示されるように、TBAFの量が増加するに従い、TBAFを加える前のメチル基の0.545ppmでのピークは徐々に減少し(エチルプロトンの0.867ppmでのと比べて)、0.12ppmおよび−0.14ppmの周辺で新しいピークが出現した。過剰配位のケイ酸塩は、テトラ配位のシランより電子が豊富であり、より保護されているので、新規の高位のピークはシリレン成分における過剰(例えば、ペンタやヘキサ)配位構造によるのかもしれない。同時に、すべてのアルキルの、あるいは芳香族の重合体のピークは、約0.04ppmだけ僅かに高磁場側にシフトした。これは、TBAFの添加の後、ポリマー鎖の中の電子密度がより高くなることを示す。加えて、Si−アリル結合が変質した場合に形成されるおそれのある、フッ化シリルのメチルプロトンは見つからなかった。したがって、上記重合体とTBAFとの反応は図2に示されるものと想定される。
次に、TBAFを実施例1の重合体を含むTHF内に滴定することより、実施例1の重合体の蛍光スペクトルの変化を調査した。具体的には、TBAFが、0,20,40,60,80,100,120×10-4Mとなった時点で、実施例1の重合体を342nmの光で励起した場合の300nmから700nmまでの蛍光スペクトルを測定した。
続いて、実施例1の重合体へのフッ素イオンを添加量と、390nmUV光の吸収の変化を、プロットした図面を図5に示す。フッ素イオンの添加量は、溶液内のケイ素に対するフッ素イオンの割合にて示している。このプロットは、特有な3ステップ線形の関係を示している。すなわち、最初のステップはケイ素の25倍の過剰TBAFより少ない場合の関係であり、プロットの傾きが緩やかである。2番目のステップは、25倍から100倍濃度のTBAF範囲であり、急な傾きを示している。そして、100倍濃度以上の最後のステップでは傾きは緩やかに戻る。
Claims (11)
- フッ素イオンと接触することで、紫外光の吸収スペクトルが変化することを特徴とする請求項1または2に記載のフッ素イオン検出用重合体。
- フッ素イオンと接触することで、蛍光スペクトルが変化することを特徴とする請求項1から3の何れか1項に記載のフッ素イオン検出用重合体。
- R7、R8の少なくとも一方が炭素数1以上20以下のアルキル基であることを特徴とする請求項5の重合体の製造方法。
- R10、R11、R14、R15のうちの少なくとも1つが炭素数1以上20以下のアルキル基であることを特徴とする請求項7の重合体の製造方法。
- 上記第1の触媒がビス((H)フェニルホスフィン)パラジウム(II)ジクロリドであることを特徴とする請求項5から8の何れか1項に記載の重合体の製造方法。
- 上記第2の触媒がヨウ化銅であることを特徴とする請求項5ないし9の何れか1項に記載の重合体の製造方法。
- 上記混合物をトリエチルアミンに溶解させて、重合させることを特徴とする請求項5ないし10の何れか1項に記載の重合体の製造方法。
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105295009A (zh) * | 2015-09-16 | 2016-02-03 | 南京邮电大学 | 一种用于氟离子检测的共轭聚电解质及其制备和应用 |
WO2020175442A1 (ja) * | 2019-02-25 | 2020-09-03 | 国立大学法人信州大学 | フッ素イオン濃度の測定方法、フッ素イオン濃度測定装置、フッ素イオン濃度検出材料の製造方法及びフッ素イオン濃度検出材料 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105295009A (zh) * | 2015-09-16 | 2016-02-03 | 南京邮电大学 | 一种用于氟离子检测的共轭聚电解质及其制备和应用 |
WO2020175442A1 (ja) * | 2019-02-25 | 2020-09-03 | 国立大学法人信州大学 | フッ素イオン濃度の測定方法、フッ素イオン濃度測定装置、フッ素イオン濃度検出材料の製造方法及びフッ素イオン濃度検出材料 |
JPWO2020175442A1 (ja) * | 2019-02-25 | 2021-11-11 | 国立大学法人信州大学 | フッ素イオン濃度の測定方法、フッ素イオン濃度測定装置、フッ素イオン濃度検出材料の製造方法及びフッ素イオン濃度検出材料 |
JP7033818B2 (ja) | 2019-02-25 | 2022-03-11 | 国立大学法人信州大学 | フッ素イオン濃度の測定方法、フッ素イオン濃度測定装置、フッ素イオン濃度検出材料の製造方法及びフッ素イオン濃度検出材料 |
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