JPH07508538A - ion sensitive compounds - Google Patents
ion sensitive compoundsInfo
- Publication number
- JPH07508538A JPH07508538A JP6522763A JP52276394A JPH07508538A JP H07508538 A JPH07508538 A JP H07508538A JP 6522763 A JP6522763 A JP 6522763A JP 52276394 A JP52276394 A JP 52276394A JP H07508538 A JPH07508538 A JP H07508538A
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- substituted
- anion
- independently
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000001875 compounds Chemical class 0.000 title claims description 36
- 150000001450 anions Chemical group 0.000 claims description 17
- -1 anion cation Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 230000009918 complex formation Effects 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 2
- NVKLTRSBZLYZHK-UHFFFAOYSA-N 4-tert-butylcalix[4]arene Chemical compound C1C(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC2=CC(C(C)(C)C)=CC1=C2O NVKLTRSBZLYZHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 2
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical class COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 description 2
- CKQQMPJQZXIYMJ-UHFFFAOYSA-N dihydrate;dihydrochloride Chemical compound O.O.Cl.Cl CKQQMPJQZXIYMJ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229960004979 fampridine Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241000400611 Eucalyptus deanei Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- CLWRFNUKIFTVHQ-UHFFFAOYSA-N [N].C1=CC=NC=C1 Chemical group [N].C1=CC=NC=C1 CLWRFNUKIFTVHQ-UHFFFAOYSA-N 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- KYCIUIVANPKXLW-UHFFFAOYSA-N dimethyl-(2-phenoxyethyl)-(thiophen-2-ylmethyl)azanium Chemical compound C=1C=CSC=1C[N+](C)(C)CCOC1=CC=CC=C1 KYCIUIVANPKXLW-UHFFFAOYSA-N 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
- G01N31/22—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Pyridine Compounds (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるため要約のデータは記録されません。 (57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】 イオン感受性化合物 発明の分野 本発明はイオン感受性（ｉｏｎ−ｓｅｎｓｉｔｉｖｅ）化合物に関する。更に詳 しくは、本発明は受容体−基質錯体（ｒｅｃｅｐｔｏｒ−ｓｕｂｓｔｒａｔｅ ｃｏｍｐｌｅｘ）の形成によりアニオン性物質（ｓｐｅｃｉｅｓ）を結合するよ うに設計された受容体からなるイオン感受性化合物に関する。[Detailed description of the invention] ion sensitive compounds field of invention The present invention relates to ion-sensitive compounds. More details In particular, the present invention provides receptor-substrate complexes. to bind anionic species by forming complexes. ion-sensitive compounds consisting of receptors designed to
発明の背景 複数の第四級アミン基からなるアニオン受容体は公知である。このような化合物 の例は、Ｐ、 Ｇ、 Ｐｏｔｖｉｎ及びＪ−Ｍ Ｌｅｈｎ、 Ｐｒｏｇ。Background of the invention Anion acceptors consisting of multiple quaternary amine groups are known. such compounds Examples are P, G, Potvin and J-M Lehn, Prog.
Ｍａｃｒｏｃｙｃｌｉｃ Ｃｈｅｍ、、 １９８７年、３巻、２１４頁に記載さ れている。Macrocyclic Chem, 1987, vol. 3, p. 214. It is.
Ｌ、 Ａ、 Ｓｕｍｍｅｒｓ著、 ［ビピリジニウム除草剤（Ｔｈｅ Ｂｉｐｙ ｒｉｄｉｎｉｕｍＨｅｒｂｉｃｉｄｅｓ） Ｊ Ａｃａｄｅｍｉｃ Ｐｒｅｓｓ 、 Ｎｅｗ Ｙｏｒｋ、 １９８０年には、除草剤への用途にジ第四級２．２′ −ビピリジニウム単位からなるある種の化合物を使用することが記載されている 。By L. A. Summers, [The Bipyridinium Herbicide (The Bipy ridinium Herbicides) J Academic Press , New York, in 1980, used diquaternary 2.2' for herbicide applications. - the use of certain compounds consisting of bipyridinium units is described .
また、Ｄ、 Ｎ、 Ｒｅ１ｎｈｏｕｄｔ、 Ｊ、 Ａｍ、 Ｃｈｅｍ、 Ｓｏｃ 、 １９９２年、１１４巻。Also, D, N, Re1nhoudt, J, Am, Chem, Soc , 1992, vol. 114.
９６７１〜９６７３頁に記載されているように、アニオンの認知のためのシステ ムで金属イオン中心が利用されてきた。A system for anion recognition, as described on pages 9671-9673. Metal ion centers have been used in many systems.
種々の応用のために新規な受容体化合物を提供するためのニーズが引き続きある 。例えば、アニオン決定のための電気化学的又は光学的センサーに含有させるこ とができる化合物についてのニーズがある。所定のアニオンのレベルを低く維持 することが必要な除去装置で使用することができる化合物についてのニーズもあ る。There continues to be a need to provide novel receptor compounds for a variety of applications. . For example, it can be included in electrochemical or optical sensors for anion determination. There is a need for compounds that can. Maintain low levels of a given anion There is also a need for compounds that can be used in removal equipment that requires Ru.
容易に合成することができる受容体化合物を提供することも望ましい。It would also be desirable to provide receptor compounds that can be easily synthesized.
発明の概要 本発明のイオン感受性化合物は、式Ａ”Ｂ’−（式中、Ａはアニオンと共に受容 体−基質錯体を形成し得るカチオンを表わし、Ｂは１種又はそれ以上の対アニオ ンを表わす）を有し、このカチオンが式又は式■ （式中、Ｒ１，Ｒ２，Ｒ３及びＲ４は、夫々独立に、水素、置換若しくは非置換 のアルキル基、置換若しくは非置換のアリール基、アルキルアミド基、アリール アミド基、アルキルスルホンアミド基、アリールスルホンアミド基又はニトロ基 であり、Ｒ５及びＲ１は、夫々独立に、Ｈ又は炭素数１〜４の低級アルキル基で あるか又はＲ５及びＲ６が一緒になってエチレン架橋基を表わし、そして ｎは０又は１である） により表わされるアニオン受容体であることを特徴とする。Summary of the invention The ion-sensitive compounds of the present invention have the formula A"B'-, where A is an acceptor along with an anion. B represents a cation capable of forming a body-substrate complex, and B represents one or more counteranions. ), and this cation has the formula or the formula ■ (In the formula, R1, R2, R3 and R4 are each independently hydrogen, substituted or unsubstituted. Alkyl group, substituted or unsubstituted aryl group, alkylamido group, aryl Amide group, alkylsulfonamide group, arylsulfonamide group or nitro group and R5 and R1 are each independently H or a lower alkyl group having 1 to 4 carbon atoms. or R5 and R6 together represent an ethylene bridging group, and n is 0 or 1) It is characterized by being an anion receptor represented by
本発明はまた、アニオンを、アニオンのための受容体であるカチオンからなる化 合物と接触させて受容体−基質錯体を形成し、錯体の形成の結果である検出可能 な変化を検知することにより溶液中のアニオンを検知する方法であって、この化 合物が本発明の化合物であることを特徴とする方法を提供する。The present invention also provides for converting anions into compounds consisting of cations that are receptors for anions. contact with a compound to form a receptor-substrate complex and detectable as a result of complex formation. This method detects anions in a solution by detecting changes in The method is characterized in that the compound is a compound of the invention.
本発明の化合物はアニオンに対して選択性を示し、アニオン、特にハロゲン化物 、特に塩化物の電気化学的及び／又は光学的検出用に有用である。The compounds of the invention exhibit selectivity towards anions, particularly halides. , particularly useful for electrochemical and/or optical detection of chlorides.
図面の簡単な説明 図１は、塩化物イオン源を添加した際の例１の化合物の観察された’ｌ（ＮＭＲ 応答のグラフ表示である。Brief description of the drawing Figure 1 shows the observed (NMR) of the compound of Example 1 upon addition of a chloride ion source. This is a graphical representation of the response.
図２は、塩化物イオン源を添加した際の例２の化合物の観察された’ＨＮＭＲ応 答のグラフ表示である。Figure 2 shows the observed 'HNMR response of the compound of Example 2 upon addition of a chloride ion source. This is a graphical representation of the answer.
発明の詳細な説明 好ましくは、Ｒ１、Ｒ１、Ｒ１及びＲ４は、夫々独立に、Ｈ１炭素数１〜２０の 置換又は非置換のアルキル基、例えば、メチル、エチル、プロピル、ブチル、ペ ンチル、ヘキシル、エイコシルである。Detailed description of the invention Preferably, R1, R1, R1 and R4 each independently represent H1 having 1 to 20 carbon atoms. Substituted or unsubstituted alkyl groups, such as methyl, ethyl, propyl, butyl, These are ethyl, hexyl, and eicosyl.
第三級アルキル基、例えば、ｔ−ブチルが特に好ましい。適当な置換基には、ア ルキルアミド、アリールアミド、アルコキシカルボニル、アリールオキシカルボ ニル、アルキルスルホンアミド、アリールスルホンアミド、アルキルカルボニル 、アルコキシ、シアノ及びニトロが含まれる。Particularly preferred are tertiary alkyl groups, such as t-butyl. Suitable substituents include a Lucylamide, arylamide, alkoxycarbonyl, aryloxycarbo Nyl, alkylsulfonamide, arylsulfonamide, alkylcarbonyl , alkoxy, cyano and nitro.
好ましくは、Ｒ１、Ｒ１、Ｒ１及びＲ４は、夫々独立に、置換又は非置換のフェ ニル基である。適当な置換基には、アルキルオキシ、アリールオキシ、アルキル アミド、アリールアミド、アルキルスルホンアミド、アリールスルホンアミド、 アルキルオキシカルボニル、アリールオキシカルボニル及びニトロが含まれる。Preferably, R1, R1, R1 and R4 are each independently substituted or unsubstituted It is a nyl group. Suitable substituents include alkyloxy, aryloxy, alkyl amides, arylamides, alkylsulfonamides, arylsulfonamides, Includes alkyloxycarbonyl, aryloxycarbonyl and nitro.
好ましくは、Ｒ５及びＲ＠は夫々メチル基である。Preferably, R5 and R@ are each a methyl group.
Ｂ２−は、Ａ２＋と一緒になって安定な化合物を形成し得る全ての適当なアニオ ンを表わす。このようなアニオンの例には、硫酸塩、硝酸塩、リン酸塩、ホウ酸 塩及びハロゲン化物、例えば沃化物が含まれる。好ましくはＢトはヘキサフルオ ロリン酸塩及びテトラフルオロホウ酸塩のような弱く配位するアニオンを表わす 。B2- can be any suitable anion which together with A2+ can form a stable compound. represents the Examples of such anions include sulfate, nitrate, phosphate, and boric acid. Included are salts and halides such as iodides. Preferably B is hexafluoro. Represents weakly coordinating anions such as rophosphate and tetrafluoroborate .
非置換及び置換カリックスアレーンの合成はよく文献に記載されている。例とし て、Ｃ，Ｄａｖｉｄ Ｇｕｔｓｃｈｅ著、 Ｃａ１ｉｘａｒｅｎｅｓ、 Ｒｏｙ ａｌＳｏｃｉｅｔｙ ｏｆ Ｃｈｅｍｉｓｔｒｙ、 １９８９年を引用する。The synthesis of unsubstituted and substituted calixarenes is well described in the literature. as an example C. David Gutsche, Calixarenes, Roy Citing alSociety of Chemistry, 1989.
本発明の化合物は、非置換又は４−置換力リックス〔４〕アレーンの１． ３− 二酸塩化物と適当なピリジン化合物、例えば、２モルの４−アミノピリジン又は ４−アミノメチルピリジンとの縮合反応を経て製造することができる。得られる ジピリジル誘導体のピリジン窒素原子の四級化により、構造式Ｉを有する化合物 が得られる。Compounds of the present invention include 1. 3- diacid chloride and a suitable pyridine compound, such as 2 moles of 4-aminopyridine or It can be produced through a condensation reaction with 4-aminomethylpyridine. can get By quaternization of the pyridine nitrogen atom of dipyridyl derivatives, compounds having structural formula I can be obtained. is obtained.
また、得られるピリジル誘導体とルテニウムジピリジルニ塩化物二水和物との反 応により構造式■を有する化合物が得られる。In addition, the reaction between the obtained pyridyl derivative and ruthenium dipyridyl dichloride dihydrate A compound having the structural formula (2) is obtained by reaction.
本発明の化合物は、上記のようなアニオンの検知方法で使用することができる。The compounds of the present invention can be used in the methods for detecting anions as described above.
錯体の形成から得られる検出可能な変化は、ＮＭＲ測定、電気化学的測定、例え ば、サイクリックボルタメトリー又は光学的測定、例えば蛍光分光法のようなど のような適当な方法によっても測定することができる。Detectable changes resulting from the formation of the complex can be detected by NMR measurements, electrochemical measurements, e.g. such as cyclic voltammetry or optical measurements, such as fluorescence spectroscopy. It can also be measured by an appropriate method such as
本発明の化合物の製造の具体的な例を下記に示す。A specific example of the production of the compound of the present invention is shown below.
使用したｐ−ｔｅｒｔ−プチルカリックス〔４〕アレーンは熱トルエン／エタノ ールから再結晶し、真空下で乾燥した。アセトンは硫酸カルシウム上に一夜放置 することによって乾燥し、次いで新鮮な硫酸カルシウムから蒸留した。The p-tert-butylcalix[4]arene used was prepared using hot toluene/ethanol. The product was recrystallized from a silica gel and dried under vacuum. Acetone was left on calcium sulfate overnight. and then distilled from fresh calcium sulfate.
ｐ−ｔｅｒｔ−プチルカリックス〔４〕アレーン（６，００ｇ、 ８．１０ミリ モル）及び無水炭酸カリウム（２，２４ｇ、 １６．２ミリモル）のスラリーを 乾燥アセトン（２００ｍＬ）中で室温で１０分間攪拌した。ブロモ酢酸エチル（ １，８１ｍＬ、 １６．２ミリモル）を添加し、反応物を１８時間室温で攪拌し た。沈殿した塩を濾過により除去し、アセトンを除去して粗生成物を残した。こ れをジクロロメタン中に入れ、水で洗浄して、所望の生成物を白色粉末として残 した。より以上の精製は必要ではなかった。収率１００％。p-tert-butylcalix [4] arene (6.00g, 8.10mm ) and anhydrous potassium carbonate (2.24 g, 16.2 mmol). Stirred in dry acetone (200 mL) at room temperature for 10 minutes. Ethyl bromoacetate ( 1.81 mL, 16.2 mmol) was added and the reaction was stirred for 18 hours at room temperature. Ta. The precipitated salts were removed by filtration and the acetone was removed leaving the crude product. child This was taken up in dichloromethane and washed with water to leave the desired product as a white powder. did. No further purification was necessary. Yield 100%.
１、 ３−二酸 ジエステル（５，２４ｇ、６．４ミリモル）を温エタノール約１．５Ｌ中に入れ 、次いで水酸化ナトリウム８０ｍＬを添加し、溶液を１２時間還流させた。エタ ノールを除去して白色固体を残し、これを真空下に乾燥した。この固体に水を添 加して褐色スラリーを形成し、濃塩酸を用いてこれをｐＨ１にまで酸性化した。1, 3-diacid The diester (5.24 g, 6.4 mmol) was placed in about 1.5 L of warm ethanol. Then 80 mL of sodium hydroxide was added and the solution was refluxed for 12 hours. Eta Removal of the nol left a white solid, which was dried under vacuum. Add water to this solid The mixture was added to form a brown slurry, which was acidified to pH 1 using concentrated hydrochloric acid.
酸性化の間に褐色からクリーム色への色変化が見られ、次いて、このスラリーの 有機成分をクロロホルム中に抽出した。有機抽出物をＨＣＩ水溶液で１回、及び ＮａＣ１で１回洗浄し、Ｍｇ５Ｏａを用いて乾燥し、クロロホルムを除去して黄 色固体５．０７ｇを残した。収率１００％。A color change from brown to cream is observed during acidification and then The organic components were extracted into chloroform. The organic extract was treated once with aqueous HCI, and Wash once with NaCl, dry with Mg5Oa, remove chloroform, and remove yellow 5.07 g of colored solid remained. Yield 100%.
１、 ３−二酸塩化物（その場で） 二酸（０，８０ｇ、１．０ミリモル）を乾燥トルエンに入れ、塩化チオニル（１ ，０ｍＬ、 ８．４ミリモル）を室温で不活性雰囲気中で添加し、次いて反応物 を１２時間還流させた。過剰の塩化チオニル及びトルエンを真空蒸留により除去 して褐色ゴム状物（粗酸塩化物）を残した。1, 3-diacid chloride (in situ) Diacid (0.80 g, 1.0 mmol) was placed in dry toluene and thionyl chloride (1 , 0 mL, 8.4 mmol) at room temperature in an inert atmosphere, then the reactants was refluxed for 12 hours. Remove excess thionyl chloride and toluene by vacuum distillation This left a brown gum (crude acid chloride).
トルエンの代わりに乾燥ジクロロメタンを使用することができる。Dry dichloromethane can be used instead of toluene.
１．３−ジピリジル誘導体 このゴム状物を乾燥ジクロロメタンに入れ、次いでカニユーレを通して乾燥アセ トニトリル中の４−アミノピリジン（０，２４ｇ、２．４ミリモル）及びトリエ チルアミン（０，１９ｍＬ、２．４ミリモル）の攪拌した溶液に室温で添加した 。攪拌すると褐色の沈殿が析出した。これを濾過により除去し、溶媒を除去して 褐色粗生成物０．８３ ｇを残した。ジクロロメタン：石油エーテルからの再結 晶でクリーム色の生成物０．４４ｇを得た。収率５２％。1.3-dipyridyl derivative This gum is placed in dry dichloromethane and then passed through a cannula into dry acetate. 4-Aminopyridine (0.24 g, 2.4 mmol) in tonitrile and trie Added to a stirred solution of thylamine (0.19 mL, 2.4 mmol) at room temperature. . Upon stirring, a brown precipitate was deposited. This is removed by filtration and the solvent is removed. 0.83 g of brown crude product remained. Dichloromethane: Recondensation from petroleum ether 0.44 g of a crystalline, cream-colored product was obtained. Yield 52%.
１．３−四級化ジピリジル誘導体 １．３−ジピリジル誘導体（０，０９ｇ、１ミリモル）をヨウ化メチル（２５ｍ Ｌ、過剰）中で１８時間還流させた。反応溶液について無色から橙色への色変化 が観察された。ヨウ化メチルを蒸留により除去して、橙色固体０．１２ｇを残し た。収率１００％。1.3-Quaternized dipyridyl derivative 1.3-dipyridyl derivative (0.09 g, 1 mmol) was dissolved in methyl iodide (25 m L, excess) for 18 hours. Color change from colorless to orange for reaction solution was observed. Methyl iodide was removed by distillation leaving 0.12 g of an orange solid. Ta. Yield 100%.
例２ １．３−ルテニウムビピリジル錯体 例１の１． ３−ジピリジル誘導体（０，２０ｇ、 ０．２６ミリモル）及びル テニウムジビリジルニ塩化物二水和物をエタノール中に入れ、５日間還流させた 。エタノールを除去し、試料を真空下で乾燥し、その後粗反応混合物を水中に入 れ、ヘキサフルオロリン酸アンモニウムを用いてＰＦ’−塩として紫色生成物が 沈殿した。収率２５％。Example 2 1.3-ruthenium bipyridyl complex Example 1, 1. 3-dipyridyl derivative (0.20 g, 0.26 mmol) and Thenium diviridyl dichloride dihydrate was placed in ethanol and refluxed for 5 days. . Remove the ethanol and dry the sample under vacuum, then place the crude reaction mixture in water. A purple product was obtained as a PF'-salt using ammonium hexafluorophosphate. It precipitated. Yield 25%.
例３ 例１の二酸塩化物をジクロロメタンに入れ、カニユーレを通してジクロロメタン 中の４−アミノメチルビリジン（０，１６ｍＬ、 １．２５ミリモル）及びトリ エチルアミン（０，Ｉ２ｍＬ、 １．２５ミリモル）の攪拌した溶液に不活性雰 囲気下に添加した。黄色から赤色への即座の色変化が観察され、反応物を更に１ ６時間室温で攪拌した。溶媒を除去して褐色粗生成物を残し、これをシリカカラ ム（６０〜２００メツシユ）を用いて精製した。溶媒、酢酸エチル・エタノール ５ ： ｌ、 ＲｆＯ，Ｉ６゜収率２０％。Example 3 Place the diacid chloride from Example 1 in dichloromethane and pass the dichloromethane through the cannula. 4-aminomethylpyridine (0.16 mL, 1.25 mmol) and tri- A stirred solution of ethylamine (0.1 mL, 1.25 mmol) was added to an inert atmosphere. It was added under ambient air. An immediate color change from yellow to red was observed and the reactants were further added to Stirred at room temperature for 6 hours. The solvent was removed leaving a brown crude product, which was washed with silica color. (60-200 mesh). Solvent, ethyl acetate/ethanol 5: l, RfO, I6° yield 20%.
このようにして形成されたビス４−メチルアミノピリジン誘導体（０，１ｇ ） をヨウ化メチル（１０ｍｌ、過剰）中で１６時間還流させた。過剰のヨウ化メチ ルを蒸留により除去して、黄色固体として四級化生成物を残した。収率１００％ 。Bis4-methylaminopyridine derivative thus formed (0.1 g) was refluxed in methyl iodide (10 ml, excess) for 16 hours. excess methioiodide was removed by distillation to leave the quaternized product as a yellow solid. Yield 100% .
例４ ’ＨＮＭＲ陽子滴定を例１． ２及び３の化合物について行った。滴定はプルツ カ−（Ｂｒｕｃｋｅｒ） ３００！ＪＨｚ分光計を用いて行った。分子ホストを ジュウテリオクロロホルムに溶解し、テトラブチルアンモニウム塩化物を０．２ ５．０．５０．１．０及び５．０モル当量の濃度に添加し、モしてＮＭＲスペク トルを記録した。条件を一定に維持するために試料を継続して流した。認識部位 でのＮＨ陽子の化学シフトの変化を記録し、塩化物の当量に対してプロットした 。例１及び２の化合物についてのプロットを夫々図１及び２に示し、これは各場 合の錯体形成を示す。図１に於いて、本発明の化合物をピリジン基が四級化され ていないモデル化合物と比較する。Example 4 'HNMR proton titration Example 1. This was carried out for compounds 2 and 3. Titration is Plutz Car (Brucker) 300! It was performed using a JHz spectrometer. molecular host Dissolve 0.2% tetrabutylammonium chloride in deuterochloroform. 5.0.50.1.0 and 5.0 molar equivalent concentrations and monitored by NMR recorded the tor. Samples were run continuously to maintain constant conditions. recognition site The change in chemical shift of the NH proton at was recorded and plotted against the chloride equivalent. . The plots for the compounds of Examples 1 and 2 are shown in Figures 1 and 2, respectively, and are shown in each case. shows the formation of a complex. In Figure 1, the pyridine group of the compound of the present invention is quaternized. Compare with a model compound that does not.
例３の化合物についての滴定結果により、塩化物イオンを有するｌ：ｌ錯体の形 成が示された。The titration results for the compound of Example 3 show that the form of the l:l complex with chloride ions The results were shown.
（ｕｌｄ’） Ａ ｃ／：’２４１ｉ：：１ｆｆ１２ｆｆ壬ＩＬ４ミ〆（”ｄｄ ） ＠ Ｃｇ’２４１ｉ：１Ａ２ｆｆ＋’１ｌｌｄ ミｒｒフロントページの続 き （５１） Ｉｎｔ、 Ｃ１，６識別記号 庁内整理番号ＧＯＩＮ ２１／７８ Ｃ８３１０−２Ｊ（７２）発明者 グールデン、アリステア−ジエイ。(uld’) A c/:’241i::1ff12ff 壬IL4mi〆(”dd ) @Cg’241i:1A2ff+’1lld Mirr front page continuation tree (51) Int, C1, 6 identification symbol Internal reference number GOIN 21/78 C8310-2J (72) Inventor Goulden, Alistair G.A.
イギリス国、オックスフォード オーエックス４２ビーニー、パードルマス ク ロス、サラスフイールド フラッノ １３０Ｉ （７２）発明者 ビア、ポール ディー。England, Oxford OEX42 beanie, puddle mask Ross, Salasfield Furano 130I (72) Inventor Beer, Paul Dee.
イギリス国、ノース オックスフオードオーエックス２８デイーエフ、ウィング ム ウェイ２ （７２）発明者 フレッチャー、ニコラス シー。United Kingdom, North Oxford, OX 28 DF, Wing Mu way 2 (72) Inventor: Fletcher, Nicholas C.
イギリス国、オックスフォード オーエックス３７エーエフ、ヘツディントン、 ライム ウオーク、ライム コート ２United Kingdom, Oxford, Oxford 37AF, Hetsington, Lime Walk, Lime Court 2
Claims (6)
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| GB9308214.7 | 1993-04-21 | ||
| GB939308214A GB9308214D0 (en) | 1993-04-21 | 1993-04-21 | Ion-sensitive compounds |
| PCT/EP1994/001192 WO1994024126A1 (en) | 1993-04-21 | 1994-04-18 | Ion-sensitive calixarenes |
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| EP (1) | EP0647224A1 (en) |
| JP (1) | JPH07508538A (en) |
| CA (1) | CA2136017A1 (en) |
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| FR2727415A1 (en) * | 1994-11-30 | 1996-05-31 | Commissariat Energie Atomique | New bi:functional ruthenium complexes |
| JP4408452B2 (en) * | 1996-04-18 | 2010-02-03 | ノバルティス アクチエンゲゼルシャフト | Fluoroionophores and their use in optical ion sensors |
| DE10297577B4 (en) * | 2001-12-21 | 2007-11-22 | Tohru Koike | Zinc complexes capable of trapping substances having anionic substituents |
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1993
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- 1994-04-18 EP EP94914394A patent/EP0647224A1/en not_active Withdrawn
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| CN105523979A (en) * | 2015-12-07 | 2016-04-27 | 江汉大学 | Azothiourea anion receptor and preparation method and application thereof |
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