JPH0224306A - Manufacture of polyacetylene - Google Patents
Manufacture of polyacetyleneInfo
- Publication number
- JPH0224306A JPH0224306A JP17570688A JP17570688A JPH0224306A JP H0224306 A JPH0224306 A JP H0224306A JP 17570688 A JP17570688 A JP 17570688A JP 17570688 A JP17570688 A JP 17570688A JP H0224306 A JPH0224306 A JP H0224306A
- Authority
- JP
- Japan
- Prior art keywords
- organic molecules
- monomolecular film
- polyacetylene
- forming
- organic
- 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.)
- Pending
Links
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 229920001197 polyacetylene Polymers 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 230000001678 irradiating effect Effects 0.000 claims abstract description 11
- 239000000758 substrate Substances 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 17
- 239000002356 single layer Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 6
- 230000003287 optical effect Effects 0.000 abstract description 6
- 230000004888 barrier function Effects 0.000 abstract description 5
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 239000010408 film Substances 0.000 description 23
- 238000006116 polymerization reaction Methods 0.000 description 12
- KZMAWJRXKGLWGS-UHFFFAOYSA-N 2-chloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-n-(3-methoxypropyl)acetamide Chemical compound S1C(N(C(=O)CCl)CCCOC)=NC(C=2C=CC(OC)=CC=2)=C1 KZMAWJRXKGLWGS-UHFFFAOYSA-N 0.000 description 4
- 150000000475 acetylene derivatives Chemical class 0.000 description 4
- 125000001165 hydrophobic group Chemical group 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 229920000015 polydiacetylene Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/35—Non-linear optics
- G02F1/355—Non-linear optics characterised by the materials used
- G02F1/361—Organic materials
Landscapes
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、単分子膜の製造に関するもので、さらに詳し
くは、電気伝導性や非線形光学効果を示すポリアセチレ
ン結合を有する単分子膜の製造方法に関するものである
。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to the production of monomolecular films, and more particularly to a method for producing monomolecular films having polyacetylene bonds that exhibit electrical conductivity and nonlinear optical effects. It is.
従来の技術
アセチレン誘導体のポリマーは、π電子共役系を持つた
め、電気伝導性や非線形光学効果を示すことから、電気
機能材料、光学機能材料として広く研究されている。BACKGROUND ART Polymers of acetylene derivatives have a π-electron conjugated system and exhibit electrical conductivity and nonlinear optical effects, so they are widely studied as electrical and optical functional materials.
これまでのポリアセチレンの製造方法としては、山川法
と呼ばれる触媒を利用した重合法がよく知られている。As a conventional method for producing polyacetylene, a polymerization method using a catalyst called the Yamakawa method is well known.
一方、親水性基と疎水性基をもつ両親媒性のアセチレン
誘導体を用いれば、ラングミュア−・ブロジェット法に
よりオングストロームオーダーの超薄膜であるアセチレ
ン誘導体の単分子膜を形成でき、さらに、累積膜を形成
することもできる。On the other hand, if an amphiphilic acetylene derivative having a hydrophilic group and a hydrophobic group is used, a monomolecular film of the acetylene derivative, which is an ultra-thin film on the order of angstroms, can be formed by the Langmuir-Blodgett method. It can also be formed.
そのため、ＬＢ法を用いたポリアセチレンの研究が盛ん
に行われている。Therefore, research on polyacetylene using the LB method is actively conducted.
発明が解決しようとする課題
ところが、単に、親水性基と疎水性基をもつ両親媒性の
アセチレン誘導体を水面上に展開しただけでは、単分子
膜を形成している直鎖状炭化水素分子内のアセチレン基
の向きは、各々の分子で様々な方向を向いており、その
のちのエネルギービームの照射による重合反応では、重
合によって形成される共役二重結合の形成方向が、アセ
チレン基の向きによるため、一方向に長い共役二重結合
を持つポリアセチレンを形成できる可能性はほとんどな
く、また、それを解決する方法も見いだされてなかった
。The problem to be solved by the invention is that simply spreading an amphiphilic acetylene derivative having a hydrophilic group and a hydrophobic group on the water surface will cause damage within the linear hydrocarbon molecules forming the monomolecular film. The orientation of the acetylene group in each molecule is various, and in the subsequent polymerization reaction by irradiation with an energy beam, the direction of formation of the conjugated double bond formed by polymerization depends on the orientation of the acetylene group. Therefore, there is little possibility of forming polyacetylene with long conjugated double bonds in one direction, and no method has been found to solve this problem.
課題を解決するための手段
本発明では、有機溶剤に溶解させた単分子膜形成用有機
分子でその分子の一端が親水基からなり、また、他端が
疎水基からなる有機分子を水面上に展開し、前記有機分
子を水面上で水面方向にバリアでかき集め、所定の表面
圧力を加えながら、水面上に単分子膜をを形成する。こ
の時、前記有機分子に対して、赤外線照射により所定の
温度をかけて単分子膜を形成する。そののち、エネルギ
ービームを照射して重合反応を行う。もしくは、エネル
ギービーム照射時にも赤外線照射を行い重合反応を行う
。以上の処理により高配向性のポリアセチレン単分子膜
を形成する。Means for Solving the Problems In the present invention, organic molecules for forming a monolayer dissolved in an organic solvent, one end of which is a hydrophilic group and the other end of which is a hydrophobic group, are placed on the water surface. The organic molecules are collected by a barrier on the water surface in the direction of the water surface, and a monomolecular film is formed on the water surface while applying a predetermined surface pressure. At this time, a monomolecular film is formed by applying infrared irradiation to the organic molecules at a predetermined temperature. Thereafter, a polymerization reaction is performed by irradiating the material with an energy beam. Alternatively, infrared ray irradiation is also performed during energy beam irradiation to perform a polymerization reaction. By the above treatment, a highly oriented polyacetylene monomolecular film is formed.
作用
本発明で用いる単分子膜形成用有機分子は水面上で水面
方向にバリアでかき集め、表面圧力を加えながら、かつ
、赤外線照射を施しながら単分子膜を形成する。水面上
に展開された前記有機分子をバリアでかき集め、加圧時
に赤外線を照射すると有機分子の密度が大になり有機分
子を構成する炭素分子および水素分子の立体的位置が一
意的に定まる。この状態はすべての有機分子に共通であ
るため、非常に整った単分子膜が形成される。このよう
な状態で形成されたアセチレン基を含む単分子膜形成用
有機分子からなる単分子膜に、エネルギービームを阿射
すると、重合反応により非常に長い共役二重結合を持つ
ポリアセチレンを形成することができる。Function The organic molecules for forming a monomolecular film used in the present invention are collected on the water surface by a barrier in the direction of the water surface, and a monomolecular film is formed while applying surface pressure and applying infrared irradiation. When the organic molecules spread out on the water surface are collected by a barrier and irradiated with infrared rays while pressurized, the density of the organic molecules increases and the steric positions of the carbon molecules and hydrogen molecules that make up the organic molecules are uniquely determined. Since this state is common to all organic molecules, a highly ordered monolayer is formed. When an energy beam is irradiated onto a monomolecular film made of organic molecules for forming a monomolecular film containing acetylene groups formed in this state, polyacetylene with extremely long conjugated double bonds is formed through a polymerization reaction. I can do it.
実施例
以下に、本発明のポリアセチレンの製造方法の実施例を
模式断面図第１図、第２図、第４図および分子構造図第
３図を用いて詳細に説明する。EXAMPLES Below, examples of the method for producing polyacetylene of the present invention will be described in detail using schematic cross-sectional views of FIGS. 1, 2, and 4 and molecular structure diagrams of FIG. 3.
本発明に使用したアセチレン基（−Ｃ＝Ｃ−）を含む単
分子膜形成用有機分子１はω−トリコシノイック酸（Ｃ
Ｈ≡Ｃ−（ＣＨ２）２９ Ｃ００Ｈ）である。有機分
子１をクロロホルムに溶解させ、水面２上に滴下し、展
開させる。クロロホルムを蒸発させたのち、バリア３で
もって、有機分子１をかき集め、一定の表面圧を加えて
水面上に単分子膜４を形成する。このとき、有機分子１
に赤外線５を照射して有機分子１を加温する。赤外線照
射にともない、有機分子１内の炭素原子および水素原子
は伸縮運動などを繰り返し行い、有機分子１が最も密に
充填された状態になる。したがって、有機分子１内にあ
るアセチレン基６の立体的向きも一意的に定められる。The organic molecule 1 for forming a monolayer containing an acetylene group (-C=C-) used in the present invention is ω-tricosinoic acid (C
H≡C-(CH2)29C00H). An organic molecule 1 is dissolved in chloroform, dropped onto the water surface 2, and spread. After the chloroform is evaporated, the organic molecules 1 are collected using the barrier 3, and a monomolecular film 4 is formed on the water surface by applying a certain surface pressure. At this time, organic molecule 1
The organic molecules 1 are heated by irradiating them with infrared rays 5. With the infrared irradiation, the carbon atoms and hydrogen atoms in the organic molecules 1 repeatedly undergo expansion and contraction movements, and the organic molecules 1 become in the most densely packed state. Therefore, the steric orientation of the acetylene group 6 within the organic molecule 1 is also uniquely determined.
このアセチレン基の立体的向きは展開されたすべての前
記有機分子内のアセチレン基に共通である。く第１図及
び第３図〉つぎに、水面上に形成された単分子膜４にエ
ネルギービームとしてＸ線７を照射する。Ｘ線７の照射
によりアセチレン基・６は重合反応を起こし、ポリアセ
チレン８を形成する。く第２図および第３図〉
つぎに、水面上に形成したポリアセチレンを含むポリマ
ー９を基板１０上に移し取り、ポリアセチレン膜を形成
する。く第４図〉
なお、本発明の実施例では表面圧を加えながら赤外線を
照射して単分子膜を形成し、そののち、エネルギービー
ムを照射し重合反応させ、水面上にポリアセチレンを形
成したが、表面圧を加える時と同様にエネルギービーム
を！ｌθ射する際にも赤外線を照射して重合反応をさせ
、ポリアセチレンを形成してもよい。This steric orientation of the acetylene group is common to the acetylene groups in all the developed organic molecules. 1 and 3> Next, the monomolecular film 4 formed on the water surface is irradiated with X-rays 7 as an energy beam. Upon irradiation with X-rays 7, the acetylene groups 6 undergo a polymerization reaction to form polyacetylene 8. 2 and 3> Next, the polymer 9 containing polyacetylene formed on the water surface is transferred onto the substrate 10 to form a polyacetylene film. In the example of the present invention, a monomolecular film was formed by irradiating infrared rays while applying surface pressure, and then an energy beam was irradiated to cause a polymerization reaction to form polyacetylene on the water surface. , an energy beam in the same way as when applying surface pressure! When irradiating lθ, infrared rays may also be irradiated to cause a polymerization reaction to form polyacetylene.
また、本発明の実施例では赤外線を照射しながら単分子
膜を形成し、そののち、エネルギービームを照射し重合
反応させ、水面上でポリアセチレンを形成し、基板上に
単分子膜を移し取る例を示したが、赤外線を照射しなが
ら単分子膜を形成し、そののち、基板上に単分子膜を移
−し取り、エネルギービームを照射し重合反応させ、ポ
リアセチレンを形成してもよい。In addition, in an example of the present invention, a monomolecular film is formed while irradiating with infrared rays, and then an energy beam is irradiated to cause a polymerization reaction to form polyacetylene on the water surface, and the monomolecular film is transferred onto a substrate. However, it is also possible to form a monomolecular film while irradiating it with infrared rays, then transfer the monomolecular film onto a substrate, and irradiate it with an energy beam to cause a polymerization reaction to form polyacetylene.
さらに、本発明の実施例では、アセチレン基を含む直鎖
状炭化水素分子としてω−トリコシノイック酸（ＣＨ≡
Ｃ−（ＣＨ２）２θ−ＣＯＯＨ）誘導体を用いたが、こ
れに関わらず、アセチレン基を含むその他の直鎖状炭化
水素分子であってもよい。Furthermore, in the embodiments of the present invention, ω-tricosinoic acid (CH≡
Although a C-(CH2)2θ-COOH) derivative was used, other linear hydrocarbon molecules containing an acetylene group may be used.
さらになお、本発明の実施例では、アセチレンのＸ線照
射により機能性膜としてポリアセチレンを形成する例を
示したが、そのほか、様々な機能性膜を形成できる。そ
の例として、ジアセチレンの重合反応によりポリジアセ
チレンを形成することができる。Furthermore, in the embodiment of the present invention, an example was shown in which polyacetylene was formed as a functional film by irradiating acetylene with X-rays, but various other functional films can be formed. As an example, polydiacetylene can be formed by a polymerization reaction of diacetylene.
発明の効果
本発明を用いることにより、より高配向性の単分子膜を
簡便に形成することができ、電気伝導性や非線形光学効
果の優れたポリアセチレンを効率よく製造することがで
きる。さらに、この製造方法では、理論的には共役二重
結合が連続して形成できるため、従来得られなかった非
常に長い直鎖状の超高分子量のポリアセチレンの製造も
可能であり、非線形光学効果を利用したデバイスの製作
には極めて宵効である。さらにまた、超共役二重結合は
超伝導性を有すると考えられており、本発明により常温
超伝導物質が製作できる可能性かある。Effects of the Invention By using the present invention, a monomolecular film with higher orientation can be easily formed, and polyacetylene with excellent electrical conductivity and nonlinear optical effects can be efficiently produced. Furthermore, with this production method, theoretically, conjugated double bonds can be formed continuously, so it is possible to produce extremely long linear ultra-high molecular weight polyacetylene, which was previously unobtainable, and nonlinear optical effects can be produced. It is extremely effective for producing devices using . Furthermore, hyperconjugated double bonds are thought to have superconductivity, and there is a possibility that room-temperature superconducting materials can be produced by the present invention.
第１図、第２図および第４図は本発明のポリアセチレン
の製造方法の実施例を示す模式断面図。
第３図は本発明のポリアセチレンの製造方法の実施例を
示す分子構造図である。
１・φ・アセチレン基を含む単分子膜形成用有機分子、
４・・・単分子膜、５・・・赤外線、６拳・・アセチレ
ン基、７・・・Ｘ線、８・拳・ポリアセチレン。
代理人の氏名 弁理士 栗野重孝 ほか１名第１図
？水面FIG. 1, FIG. 2, and FIG. 4 are schematic cross-sectional views showing an example of the method for producing polyacetylene of the present invention. FIG. 3 is a molecular structure diagram showing an example of the method for producing polyacetylene of the present invention. Organic molecules for forming monolayers containing 1.φ.acetylene groups,
4... Monomolecular film, 5... Infrared rays, 6... Acetylene group, 7... X-rays, 8... Fists/Polyacetylene. Name of agent: Patent attorney Shigetaka Kurino and one other person Figure 1? water surface
Claims (4)
）を含む単分子膜形成用有機分子を水面上に展開する工
程と、前記水面上に展開した前記有機分子を集め、所定
の表面圧を加える工程と、有機分子に対して赤外線照射
を施す工程と前記有機分子を所定の基板に移し取る工程
と、エネルギービームを前記有機分子に照射する工程と
を備えてなることを特徴とするポリアセチレンの製造方
法。(1) Acetylene group (-C≡C-
) on the water surface, a step of collecting the organic molecules spread on the water surface and applying a predetermined surface pressure, and a step of irradiating the organic molecules with infrared rays. A method for producing polyacetylene, comprising the steps of: transferring the organic molecule to a predetermined substrate; and irradiating the organic molecule with an energy beam.
−）を含む単分子膜形成用有機分子に対して赤外線照射
を施すことを特徴とする特許請求の範囲第１項記載のポ
リアセチレンの製造方法。(2) At the same time as applying surface pressure, the acetylene group (-C≡C
2. The method for producing polyacetylene according to claim 1, characterized in that the organic molecules for forming a monomolecular film containing (-) are irradiated with infrared rays.
−）を含む単分子膜形成用有機分子に対して赤外線照射
を施したのちエネルギービームを前記有機分子に照射を
施す、あるいは、表面圧を加えると同時にアセチレン基
（−Ｃ≡Ｃ−）を含む単分子膜形成用有機分子に対して
赤外線照射を施すとともにエネルギービームを前記有機
分子に照射する際にも赤外線照射を施し、そののち、前
記有機分子を所定の基板に移し取ることを特徴とする特
許請求の範囲第１項又は第２項記載のポリアセチレンの
製造方法。(3) At the same time as applying surface pressure, the acetylene group (-C≡C
-) is irradiated with infrared rays to an organic molecule for forming a monolayer containing an acetylene group (-C≡C-), and then an energy beam is applied to the organic molecule, or at the same time a surface pressure is applied. The organic molecules for forming a monolayer film are irradiated with infrared rays, and when the organic molecules are irradiated with an energy beam, the organic molecules are also irradiated with infrared rays, and then the organic molecules are transferred to a predetermined substrate. A method for producing polyacetylene according to claim 1 or 2.
あることを特徴とする特許請求の範囲第１項記載のポリ
アセチレンの製造方法。(4) The method for producing polyacetylene according to claim 1, wherein the substance containing an acetylene group is tricosinoic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17570688A JPH0224306A (en) | 1988-07-14 | 1988-07-14 | Manufacture of polyacetylene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17570688A JPH0224306A (en) | 1988-07-14 | 1988-07-14 | Manufacture of polyacetylene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0224306A true JPH0224306A (en) | 1990-01-26 |
Family
ID=16000824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17570688A Pending JPH0224306A (en) | 1988-07-14 | 1988-07-14 | Manufacture of polyacetylene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0224306A (en) |
-
1988
- 1988-07-14 JP JP17570688A patent/JPH0224306A/en active Pending
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