JPS6337343B2 - - Google Patents
Info
- Publication number
- JPS6337343B2 JPS6337343B2 JP54060956A JP6095679A JPS6337343B2 JP S6337343 B2 JPS6337343 B2 JP S6337343B2 JP 54060956 A JP54060956 A JP 54060956A JP 6095679 A JP6095679 A JP 6095679A JP S6337343 B2 JPS6337343 B2 JP S6337343B2
- Authority
- JP
- Japan
- Prior art keywords
- membrane
- film
- light
- potential
- membrane potential
- 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.)
- Expired
Links
- 239000012528 membrane Substances 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229920000642 polymer Polymers 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- -1 benzospiropyran compound Chemical class 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000007699 photoisomerization reaction Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- GTKRFUAGOKINCA-UHFFFAOYSA-M chlorosilver;silver Chemical compound [Ag].[Ag]Cl GTKRFUAGOKINCA-UHFFFAOYSA-M 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- MHCGTEBQHSVRDP-UHFFFAOYSA-N 3-(3',3'-dimethyl-6-nitrospiro[chromene-2,2'-indole]-1'-yl)propanoic acid Chemical class O1C2=CC=C([N+]([O-])=O)C=C2C=CC21N(CCC(O)=O)C1=CC=CC=C1C2(C)C MHCGTEBQHSVRDP-UHFFFAOYSA-N 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000007697 cis-trans-isomerization reaction Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 229940021013 electrolyte solution Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002706 hydrostatic effect Effects 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 230000010365 information processing Effects 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001308 poly(aminoacid) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Optical Communication System (AREA)
- Photometry And Measurement Of Optical Pulse Characteristics (AREA)
Description
【発明の詳細な説明】
本発明は、光を吸収して異性化反応を生ずる物
質を利用して、膜の膜電位を光照射によつて可逆
的に制御する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method of reversibly controlling the membrane potential of a membrane by light irradiation using a substance that absorbs light and causes an isomerization reaction.
同一の分子式を有するが性質の異なるような関
係にある化合物を異性体といい、その間の構造変
化を異性化と呼び、光により誘起される場合は光
異性化反応として知られている。これらの異性体
はその構造が異なることにより相互に物理化学的
な性質が異なる。光異性化反応としては、シス−
トランス異性化、ラジカル生成、イオン化、ケト
−エノル互変異性、２重結合の移動、プロトン転
移などがよく知られている。 Compounds that have the same molecular formula but different properties are called isomers, and the structural changes between them are called isomerization, and when induced by light, it is known as a photoisomerization reaction. These isomers have different physicochemical properties due to their different structures. As a photoisomerization reaction, cis-
Trans isomerization, radical generation, ionization, keto-enol tautomerism, double bond migration, proton transfer, etc. are well known.
従来、工業的にはかかる光異性化反応に伴う色
の変化、すなわちフオトクロミツクな性質を利用
するものが多くあつた。スピロピラン化合物もよ
く知られたフオトクロミツクな化合物であるが、
スピロピラン化合物を含めてフオトクロミツク以
外の分子の物理化学的な性質の変化を利用するも
のはきわめて少ないのが現状である。 Conventionally, there have been many industrial methods that utilize the color change accompanying such photoisomerization reactions, that is, the photochromic properties. Spiropyran compounds are also well-known photochromic compounds,
At present, there are very few methods that utilize changes in the physical and chemical properties of molecules other than photochromics, including spiropyran compounds.
本発明者らは、かかる観点から光異性化反応に
伴う分子の物理化学的な性質の変化を工業的に利
用する方法を提供することを目的として鋭意研究
の結果、スピロピラン化合物を主鎖または側鎖に
含む高分子よりなる膜に光照射を行なうと、その
膜の膜電位が微妙にコントロールできることを見
い出し、本発明に到達したものである。 From this point of view, the present inventors have conducted extensive research with the aim of providing a method for industrially utilizing changes in the physicochemical properties of molecules accompanying photoisomerization reactions. The inventors have discovered that by irradiating a film made of polymers contained in chains with light, the membrane potential of the film can be delicately controlled, leading to the present invention.
すなわち本発明は、光異性化するスピロピラン
化合物を主鎖または側鎖に含み、かつ親水性基を
有する高分子化合物からなる膜に光照射して該膜
の膜電位を変化させることを特徴とする光照射に
よる膜電位の制御方法である。 That is, the present invention is characterized in that a film made of a polymer compound containing a photoisomerizable spiropyran compound in its main chain or side chain and having a hydrophilic group is irradiated with light to change the membrane potential of the film. This is a method of controlling membrane potential using light irradiation.
本発明によれば膜に光を照射するというきわめ
て簡便な方法によつて膜の膜電位を微妙に、かつ
可逆的に調整することができる。 According to the present invention, the membrane potential of a membrane can be finely and reversibly adjusted by an extremely simple method of irradiating the membrane with light.
本発明に用いられる膜を構成する高分子化合物
は、光異性化するスピロピラン化合物を主鎖また
は側鎖に含み、かつ親水性基を有するものであ
る。 The polymer compound constituting the membrane used in the present invention contains a photoisomerizable spiropyran compound in its main chain or side chain, and has a hydrophilic group.
本発明においてスピロピラン化合物としては、
光異性化するものであればいかなるものでも使用
できる。かかるスピロピラン化合物としては、た
とえばインドリノベンゾスピロピラン誘導体、
（たとえばニトロ基、ハロゲン、メトキシ基など
の各種置換基を有するもの）、ベンゼン環のどち
らかがアントラセンやフエナンスレンなどの芳香
族縮合環に代わつたインドリノナフトスピロピラ
ン誘導体、インドリノフエナンスロスピロピラン
誘導体あるいはインドリン環に代つたチアゾリノ
ベンゾスピロピラン誘導体などがあげられるが、
最も好ましいのはベンゾスピロピラン誘導体であ
る。 In the present invention, spiropyran compounds include:
Any material can be used as long as it can be photoisomerized. Such spiropyran compounds include, for example, indolinobenzospiropyran derivatives,
(for example, those having various substituents such as nitro group, halogen, methoxy group, etc.), indolinonaphthospiropyran derivatives in which one of the benzene rings is replaced with an aromatic condensed ring such as anthracene or phenanthrene, indolinophenanthrospiropyran derivatives, or Examples include thiazolinobenzospiropyran derivatives that replaced the indoline ring.
Most preferred are benzospiropyran derivatives.
かかるスピロピラン化合物を高分子の主鎖また
は側鎖に含ませるには種々の方法を採用すること
ができるが、たとえば親水性基を含むスピロピラ
ン化合物を単独重合させる方法やスピロピラン化
合物と他の適当なモノマーとを共重合させるなど
の方法がとられる。 Various methods can be employed to incorporate such a spiropyran compound into the main chain or side chain of a polymer, such as a method in which a spiropyran compound containing a hydrophilic group is homopolymerized, or a method in which a spiropyran compound and other suitable monomers are polymerized. Methods such as copolymerization with
本発明においては膜を構成する高分子化合物
は、得られた膜が水分子を自由に通過させるため
に親水性基を有するものであることが必要であ
る。親水性基としては、たとえばカルボキシル
基、スルホン酸基、フエノール性水酸基あるいは
それらの塩、アミノ基などの塩基性基、アンモニ
ウム塩、水酸基などがあげられる。本発明におい
て使用される高分子化合物としては、たとえば、
ポリビニルアルコール、ポリアクリル酸、ポリメ
タクリル酸、ポリエチレングリコールのブロツク
共重合体、ヒドロキシエチルメタクリレートの重
合体、エチレングリコールジメタクリレートの重
合体、セルロース、酢酸セルロース、キチン、ポ
リアミノ酸などがあげられる。 In the present invention, the polymer compound constituting the membrane needs to have a hydrophilic group so that the resulting membrane can freely pass water molecules. Examples of the hydrophilic group include a carboxyl group, a sulfonic acid group, a phenolic hydroxyl group or a salt thereof, a basic group such as an amino group, an ammonium salt, a hydroxyl group, and the like. Examples of the polymer compounds used in the present invention include:
Examples include block copolymers of polyvinyl alcohol, polyacrylic acid, polymethacrylic acid, and polyethylene glycol, polymers of hydroxyethyl methacrylate, polymers of ethylene glycol dimethacrylate, cellulose, cellulose acetate, chitin, and polyamino acids.
本発明に用いられる光異性化するスピロピラン
化合物を主鎖または側鎖に含み、かつ親水性基を
有する高分子化合物の好適な具体例としては次の
ようなものがあげられる。 Preferred specific examples of the polymer compound containing a photoisomerizable spiropyran compound in its main chain or side chain and having a hydrophilic group used in the present invention include the following.
このような高分子化合物を膜化するには、従来
公知の方法を採用することができる。たとえば高
分子化合物を適当な溶媒に溶解したのち、得られ
た溶液を流延することもできるし、また高分子化
合物自体が水溶性であるときは適当な架橋剤を加
えたのち膜化することもできる。 Conventionally known methods can be used to form a film from such a polymer compound. For example, it is possible to dissolve a polymer compound in an appropriate solvent and then cast the resulting solution, or if the polymer compound itself is water-soluble, it can be formed into a film after adding an appropriate crosslinking agent. You can also do it.
本発明においては、上記のようにして得られた
膜を利用して光照射によつて膜電位を変化させ
る。ここにいう膜電位とは、２種の電解質溶液が
膜によつてへだてられている場合に膜の両側に生
ずる電位差を意味する。 In the present invention, the membrane potential is changed by light irradiation using the membrane obtained as described above. The term "membrane potential" as used herein means the potential difference that occurs on both sides of a membrane when two types of electrolyte solutions are separated by the membrane.
本発明における光照射には、公知の光源、たと
えばキセノンランプ、高圧水銀ランプなどが用い
られるが、目的に応じ色ガラスフイルターで適当
な波長を選択して照射するのが望ましい。膜電位
の測定は公知の方法によつて行なえる。すなわ
ち、向い合つて穴のあいた２つのセルの間に膜を
はさみ、２つのセルにそれぞれ低濃度の電解質と
高濃度の電解質を加えて両方の液面を等しくし、
実質的に膜にかかる静水圧を等しくしたのち２つ
のセルにそれぞれ電極を挿入し、それを電位差計
に接続することによつて、電位差を測定すること
ができる。光照射のためには、セルの一面を石英
板などのように光吸収の少ない材質のもので作製
しておけばよい。 For light irradiation in the present invention, a known light source such as a xenon lamp or a high-pressure mercury lamp is used, but it is preferable to select an appropriate wavelength using a colored glass filter depending on the purpose. Membrane potential can be measured by a known method. In other words, a membrane is sandwiched between two facing cells with holes, and a low concentration electrolyte and a high concentration electrolyte are added to each cell to equalize the liquid level in both cells.
After substantially equalizing the hydrostatic pressure across the membranes, the potential difference can be measured by inserting an electrode into each of the two cells and connecting it to a potentiometer. For light irradiation, one side of the cell may be made of a material with low light absorption, such as a quartz plate.
本発明によれば光照射によつて膜電位を可逆的
に変化させることができるし、また光照射の強度
や時間を調整することにより膜電位をきわめて微
妙に調整することができる。光によつて膜電位が
変化させられれば、光通信などのデバイスとして
光信号の電気信号への変換が可能となるので、本
発明は光情報処理産業、オプトエレクトロニクス
分野での利用が大いに期待される。 According to the present invention, the membrane potential can be reversibly changed by light irradiation, and the membrane potential can be adjusted very delicately by adjusting the intensity and time of the light irradiation. If the membrane potential is changed by light, it becomes possible to convert an optical signal into an electrical signal as a device for optical communication, so the present invention is highly expected to be used in the optical information processing industry and the optoelectronics field. Ru.
以下実施例をあげて本発明をさらに具体的に説
明する。 The present invention will be explained in more detail below by giving examples.
実施例 １
光異性化物質として1′，3′，3′−トリメチル−
６−ニトロ−８−メタクリロキシメチルベンゾス
ピロピラン0.2ｇを、メタクリル酸0.43ｇとエチ
レングリコールジメタクリレート0.15ｇとジメチ
ルホルムアミド0.15mlとの混液に溶解し、N2置
換後、10μのポリエチレンのスペーサーを入れた
ガラス板にはさみ、ついで、これに１×106radの
ガンマー線を照射し、ガラス板からはがして赤色
透明状の膜を得た。得た膜をエタノールで数回洗
浄した後、再びエタノール中に２昼夜浸漬して、
未反応のモノマーを除去した。この試料を脱イオ
ン水で洗浄し、エタノールを除去後、1/500Ｎの
Nacl水溶液中に２日間浸漬した。Example 1 1′,3′,3′-trimethyl- as a photoisomerizable substance
Dissolve 0.2 g of 6-nitro-8-methacryloxymethylbenzospiropyran in a mixture of 0.43 g of methacrylic acid, 0.15 g of ethylene glycol dimethacrylate, and 0.15 ml of dimethylformamide, and after replacing with N2 , add a 10μ polyethylene spacer. Then, it was irradiated with gamma rays of 1×10 6 rad and peeled off from the glass plate to obtain a red transparent film. After washing the obtained membrane several times with ethanol, it was immersed again in ethanol for two days and nights.
Unreacted monomers were removed. This sample was washed with deionized water to remove ethanol, and then 1/500N
It was immersed in NaCl aqueous solution for 2 days.
低濃度側を1/500Ｎ、高濃度側を1/10Ｎとした
Nacl水溶液を上記膜でへだて、それぞれ低濃度
側、高濃度側に浸した銀−塩化銀比較電極を電位
差計に接続して暗黒中20℃で両室の電位差を測定
したところ、−42.5ｍＶの電位差を得た。これに
470nｍ以上の可視光を高圧水銀ランプから得、
15cmの距離から膜に照射した。膜の赤色の退色と
ともに電位差は変化し、無色透明な膜になつた時
点で電位差は−33.5ｍＶへと変化した。光照射を
とめると、再びもとの電位差へと回復した。 The low concentration side was set to 1/500N, and the high concentration side was set to 1/10N.
When the NaCl aqueous solution was separated through the above membrane and the silver-silver chloride reference electrodes immersed in the low and high concentration sides were connected to a potentiometer and the potential difference between the two chambers was measured at 20°C in the dark, -42.5 mV. The potential difference was obtained. to this
Obtain visible light of 470 nm or more from a high-pressure mercury lamp,
The membrane was irradiated from a distance of 15 cm. The potential difference changed as the red color of the film faded, and when the film became colorless and transparent, the potential difference changed to -33.5 mV. When the light irradiation was stopped, the potential difference returned to the original level.
実施例 ２
1′，3′，3′−トリメチル−６−ニトロ−８−メ
タクリロキシメチルベンゾスピロピラン0.1ｇを、
メタクリル酸−２−ヒドロキシエチル0.3ｇとエ
タノール0.1ｇとの混液に溶解した。ついで70μの
スペーサーを用いた他は実施例１と同様にして膜
状に重合し、試料の調整も行なつた。Example 2 0.1 g of 1',3',3'-trimethyl-6-nitro-8-methacryloxymethylbenzospiropyran,
It was dissolved in a mixture of 0.3 g of 2-hydroxyethyl methacrylate and 0.1 g of ethanol. Next, polymerization was carried out to form a film in the same manner as in Example 1 except that a 70μ spacer was used, and the sample was also prepared.
低濃度側を1/500Ｎ、高濃度側を1/10Ｎとした
Nacl水溶液を上記膜でへだてて銀−塩化銀比較
電極を電位差計に接続して暗黒中で両室の電位差
を測定したところ−22.0ｍＶの電位差を得た。こ
れに470nｍ以上の可視光を高圧水銀ランプから
得、15cmの距離から膜に照射したところ膜の赤色
の退色とともに電位差は変化し、無色透明な膜に
なつた時点で電位差は−24.0ｍＶへと変化した。
光照射をとめると再びもとの電位差へと回復し
た。さらに、赤外部の光を照射したが膜電位の変
化は観測されなかつた。 The low concentration side was set to 1/500N, and the high concentration side was set to 1/10N.
When the NaCl aqueous solution was separated through the membrane and the silver-silver chloride reference electrode was connected to a potentiometer and the potential difference between the two chambers was measured in the dark, a potential difference of -22.0 mV was obtained. When visible light of 470 nm or more was obtained from a high-pressure mercury lamp and irradiated onto the film from a distance of 15 cm, the potential difference changed as the red color of the film faded, and when the film became colorless and transparent, the potential difference decreased to -24.0 mV. changed.
When the light irradiation was stopped, the potential difference returned to the original level. Furthermore, no change in membrane potential was observed despite irradiation with infrared light.
実施例 ３
低濃度側の塩濃度を1/500Ｎ、高濃度側の塩濃
度を1/30Ｎとした他は実施例１と同様にして実験
を行なつた。暗黒下では膜電位は−36.0ｍＶであ
つたが、470nｍ以上の可視光を照射すると、膜
は脱色し、それに伴つて最初は−35.0ｍＶに膜電
位は上昇したが、その後３分位ですみやかに−
45.0ｍＶへと実施例１とは逆に膜電位がマイナス
側に大きくなることが観測された。光照射をとめ
ると再びもとの電位に回復した。Example 3 An experiment was conducted in the same manner as in Example 1, except that the salt concentration on the low concentration side was 1/500N and the salt concentration on the high concentration side was 1/30N. The membrane potential was -36.0 mV in the dark, but when irradiated with visible light of 470 nm or more, the membrane bleached, and the membrane potential rose to -35.0 mV at first, but then quickly changed in about 3 minutes. ni-
Contrary to Example 1, it was observed that the membrane potential increased to 45.0 mV on the negative side. When the light irradiation was stopped, the potential returned to the original level.
比較例 １
光異性化物質としてビニル基を含まない1′，
3′，3′−トリメチル−６−ニトロ−８−アセトキ
シメチルベンゾスピロピラン0.2ｇを用いた他は
実施例１と同様にして膜を得た。得られた膜は水
で洗浄したのち1/500ＮのNacl水溶液中に２日間
浸漬し、ついで実施例１と同様にして実験を行な
つた。光照射前には−55.3ｍＶであつた膜電位は
これに470nｍ以上の可視光を照射したが膜電位
は−53.2ｍＶへ変化したのみであつた。Comparative example 1 1′, which does not contain vinyl groups as a photoisomerizable substance,
A membrane was obtained in the same manner as in Example 1, except that 0.2 g of 3',3'-trimethyl-6-nitro-8-acetoxymethylbenzospiropyran was used. The obtained membrane was washed with water and then immersed in a 1/500N NaCl aqueous solution for 2 days, and then an experiment was conducted in the same manner as in Example 1. The membrane potential, which was -55.3 mV before light irradiation, only changed to -53.2 mV when visible light of 470 nm or more was irradiated.
このように、スピロピラン化合物を単に高分子
化合物に混合したものでは光照射による膜電位の
変化は小さい。また、混合の場合は有機溶剤によ
つてスピロピラン化合物が膜から容易に脱離しや
すいために十分なる耐久性を有しない欠点をも有
する。 As described above, when a spiropyran compound is simply mixed with a polymer compound, the change in membrane potential due to light irradiation is small. In addition, in the case of mixing, the spiropyran compound is easily detached from the film by an organic solvent, so that it has the disadvantage that it does not have sufficient durability.
Claims (1)
は側鎖に含み、かつ親水性基を有する高分子化合
物からなる膜に光照射して該膜の膜電位を変化さ
せることを特徴とする光照射による膜電位の制御
方法。 ２ スピロピラン化合物がベンゾスピロピラン化
合物である特許請求の範囲第１項記載の制御方
法。[Scope of Claims] 1. A film comprising a polymer compound containing a photoisomerizable spiropyran compound in its main chain or side chain and having a hydrophilic group is irradiated with light to change the membrane potential of the film. A method of controlling membrane potential using light irradiation. 2. The control method according to claim 1, wherein the spiropyran compound is a benzospiropyran compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6095679A JPS55152426A (en) | 1979-05-16 | 1979-05-16 | Membrane potential controlling method with radiation of light |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6095679A JPS55152426A (en) | 1979-05-16 | 1979-05-16 | Membrane potential controlling method with radiation of light |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55152426A JPS55152426A (en) | 1980-11-27 |
| JPS6337343B2 true JPS6337343B2 (en) | 1988-07-25 |
Family
ID=13157347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6095679A Granted JPS55152426A (en) | 1979-05-16 | 1979-05-16 | Membrane potential controlling method with radiation of light |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55152426A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2509573B2 (en) * | 1986-07-25 | 1996-06-19 | 株式会社東芝 | Light / heat-frequency conversion function film |
-
1979
- 1979-05-16 JP JP6095679A patent/JPS55152426A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55152426A (en) | 1980-11-27 |
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