KR20030083778A - Novel pyrrole compound and manufacturing method thereof - Google Patents
Novel pyrrole compound and manufacturing method thereof Download PDFInfo
- Publication number
- KR20030083778A KR20030083778A KR1020020021947A KR20020021947A KR20030083778A KR 20030083778 A KR20030083778 A KR 20030083778A KR 1020020021947 A KR1020020021947 A KR 1020020021947A KR 20020021947 A KR20020021947 A KR 20020021947A KR 20030083778 A KR20030083778 A KR 20030083778A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- compound represented
- dodecanoate
- integer
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
Abstract
Description
본 발명은 유기 초박막 제조시 전도성이 개선되어 전자재료용 유기 전도체로서 사용시 우수한 전도성을 지닌 반도체 소자로 사용될 수 있는 신규한 함피롤 화합물과 이를 제조하는 방법에 관한 것이다.The present invention relates to a novel hampyrrole compound which can be used as a semiconductor device having excellent conductivity when used as an organic conductor for an electronic material with improved conductivity in manufacturing an organic ultra thin film, and a method of manufacturing the same.
기존에 전자재료로서는 주로 무기 반도체인 실리콘과 갈륨, 비소 등의 물질이 사용되었으나, 유기 반도체의 가장 큰 특성 중의 하나인 전자적 성질을 조절할 수 있다는 매력적인 점으로 인해 유기반도체 재료에 관한 기술이 많이 개시되어 있다. 그러나, 전도성을 띠는 유기물질로 스핀 코팅(Spin coating) 등의 방법을 통해 박막을 제조하는 경우 나노미터 단위까지의 초박막으로 제조가 힘들고, 배향성의 문제로 경량화와 전도체로서의 기능이 제대로 발휘되지 못하고 있다.Conventionally, as an electronic material, materials such as silicon, gallium, and arsenic, which are inorganic semiconductors, have been mainly used. However, due to the attractiveness of controlling electronic properties, one of the biggest characteristics of organic semiconductors, many technologies regarding organic semiconductor materials have been disclosed. have. However, when a thin film is manufactured by using a conductive coating, such as spin coating, it is difficult to manufacture a thin film up to nanometers, and due to the orientation problem, the weight and the function as a conductor are not properly exhibited. have.
이와같은 문제를 극복하기 위해 최근들어 Langumir-Blagett(이하, LB라 함) 기법에 의해 전도성 유기초박막을 제조하는 방법이 많이 시도되어 소개되어져 왔다. 그러나, LB 초박막을 제조하는 데 있어 전도성 물질에 장쇄 탄화수소를 도입시켜 양친매성의 전도성 유기물질을 합성하는 방법은 매우 복잡하고 돕핑의 번거로움 등의 문제가 있었다. 이를 해결하기 위해 지방산염 매트릭스 LB막을 제조한 후, 막 내부로 전도성 물질을 도입시키는 연구가 많이 시도되어졌지만, 이 방법 역시 매트릭스로 인한 막의 두께 조절 문제와 LB 다층막 내부에서의 전도성 물질의 합성 여부의 어려움이 있었다.In order to overcome such a problem, a method of manufacturing a conductive organic ultra thin film has been introduced in recent years by the Langumir-Blagett (hereinafter, referred to as LB) technique. However, in preparing LB ultra-thin films, a method of synthesizing amphiphilic conductive organic materials by introducing long-chain hydrocarbons into the conductive material has been very complicated and hassles such as troublesome doping. In order to solve this problem, there have been many attempts to introduce a conductive material into the film after preparing a fatty acid matrix LB film, but this method also has a problem of controlling the thickness of the film due to the matrix and whether the conductive material is synthesized in the LB multilayer film. There was a difficulty.
따라서, 본 발명에서는 앞에서 기술한 종래의 문제점을 해결하기 위해 연구를 거듭한 결과, 전도성 물질에 보다 쉬운 방법으로 지방산 물질을 도입하여 뛰어난 전도성을 가지며 LB 기법에 의해 직접 초박막 제조를 가능하게 할 수 있는 신규한 함피롤 화합물을 제공하는 데 그 목적이 있다.Therefore, in the present invention, as a result of repeated studies to solve the above-described conventional problems, by introducing fatty acids in an easier way to the conductive material has excellent conductivity and can directly manufacture the ultra-thin film by the LB technique It is an object to provide a novel hampyrrole compound.
또한, 본 발명은 상기와 같은 함피롤 화합물을 제조하는 방법을 제공하는 데도 그 목적이 있다.In addition, an object of the present invention is to provide a method for producing such a hampyrrole compound.
상기와 같은 목적을 달성하기 위한 본 발명의 신규한 함피롤 화합물은 다음화학식 1로 표시되는 것임을 그 특징으로 한다.The novel hampyrrole compound of the present invention for achieving the above object is characterized by that represented by the following formula (1).
화학식 1Formula 1
상기 식에서, M은 에스테르기를 갖는 화합물이나 카르복실기이고, n은 10 내지 20의 정수이다.In the above formula, M is a compound or carboxyl group having an ester group, and n is an integer of 10 to 20.
상기 화학식 1로 표시되는 함피롤 화합물 중 M이 에스테르기를 갖는 화합물인 경우는 다음 화학식 2로 표시되는 화합물과 요오도알킬, 탄산칼슘을 아세톤 하에서 에스테르화시키고 정제과정을 거쳐서 순수한 알킬 브로모 도데카노에이트를 제조하는 단계; 및 상기 알킬 브로모 도데카노에이트에 다음 화학식 3으로 표시되는 피롤염을 반응시키는 단계를 거쳐 얻어진다.In the case where M is a compound having an ester group, the compound of Formula 2, iodoalkyl, and calcium carbonate are esterified under acetone, and purified through pure alkyl bromo dodecanoate. Preparing a; And reacting the alkyl bromo dodecanoate with a pyrrole salt represented by the following Formula 3.
화학식 2Formula 2
상기 식에 있어서, n은 10 내지 20의 정수이다.In the formula, n is an integer of 10 to 20.
화학식 3Formula 3
그리고, 상기 화학식 1로 표시되는 화합물 중 함피롤 화합물 중 M이 카르복실기인 화합물은 상기 단계 후 애시드화시키는 단계를 추가적으로 수행하여 얻어진다.In addition, the compound in which M is a carboxyl group in the hampyrrole compound of the compound represented by Formula 1 is obtained by additionally performing an acidification step after the step.
도 1은 본 발명 실시예 1, 2에 따라 얻어진 화합물의 적외선 흡수 스펙트럼이다.1 is an infrared absorption spectrum of a compound obtained according to Examples 1 and 2 of the present invention.
(a)실시예 1에 따라 얻어진 피롤릴 도데카노에이트(a) Pyrrolyl dodecanoate obtained according to Example 1
(b)실시예 2에 따라 얻어진 12-피롤릴 도데카노익 애시드(b) 12-pyrrolyl dodecanoic acid obtained according to Example 2
이와같은 본 발명을 더욱 상세하게 설명하면 다음과 같다.The present invention will be described in more detail as follows.
본 발명은 상기 화학식 1로 표시되는 신규한 함피롤 화합물에 관한 것으로서, 이는 초박막을 제조하여 유기전도체로 사용시 전자적 성질의 조절이 가능한 우수한 전도성을 가지며, 친수성기와 소수성을 동시에 지닌 안정한 화합물로서, Langumir-Blagett 유기 초박막의 제조가 직접 가능하여 우수한 배향성과 더불어 기타 유기박막에 비해 한층 전도성을 높이는 효과가 있다.The present invention relates to a novel hampyrrole compound represented by the formula (1), which has an excellent conductivity that can control the electronic properties when used as an organic conductor by producing an ultra-thin film, a stable compound having both hydrophilic and hydrophobic, Langumir- Blagett organic ultra thin film can be manufactured directly, and it has an excellent orientation and an effect of increasing conductivity compared with other organic thin films.
본 발명에 따른 상기 화학식 1의 화합물을 예를들어 구체적으로 설명하면, M은 카르복실기, 에스테르기, 알킬기 등일 수 있다.Referring to the compound of Formula 1 according to the present invention in detail, for example, M may be a carboxyl group, an ester group, an alkyl group.
이와같은 화학식 1로 표시되는 화합물들의 제조방법을 설명하면 다음과 같다.Referring to the preparation method of the compound represented by the formula (1) as follows.
상기 화학식 2로 표시되는 화합물과 요오도알킬, 탄산칼슘을 아세톤 하에서 에스테르화시키고 정제과정을 거쳐서 순수한 알킬 브로모 도데카노에이트를 제조한 후, 여기에 상기 화학식 3으로 표시되는 화합물을 반응시킨다.After the compound represented by the formula (2), iodoalkyl, calcium carbonate is esterified under acetone and purified to prepare pure alkyl bromo dodecanoate, the compound represented by the formula (3) is reacted thereto.
제조과정을 반응식으로 나타내면 다음과 같다.Representation of the manufacturing process is as follows.
또는, 상기 반응식 1과 같은 반응을 거친 다음, 애시드화시켜 얻어진다.Alternatively, the reaction is carried out as in Scheme 1, followed by acidification.
제조과정을 반응식으로 나타내면 다음과 같다.Representation of the manufacturing process is as follows.
먼저, 상기 화학식 2로 표시되는 화합물의 구체적인 화합물의 예로는 12-브로모도데카노익 애시드 등을 들 수 있다.First, examples of specific compounds of the compound represented by Formula 2 include 12-bromododecanoic acid and the like.
이와같은 화학식 2로 표시되는 화합물과 요오도알킬, 탄산칼슘, 아세톤을 혼합하여 57∼60℃에서 1∼5시간 환류시킨 후, 반응용액을 여과시켜 탄산칼슘을 걸러낸다. 그리고 나서, 아세톤을 증류시킨 후, 정제과정을 거쳐 무색의 액체상으로 알킬 브로모 도데카노에이트를 얻을 수 있다.The compound represented by the formula (2), iodoalkyl, calcium carbonate and acetone are mixed and refluxed at 57 to 60 ° C. for 1 to 5 hours, and then the reaction solution is filtered to filter out calcium carbonate. Then, after distilling the acetone, it is possible to obtain alkyl bromo dodecanoate as a colorless liquid through purification.
여기서, 요오도알킬의 구체적인 예로는 요오도메틸, 요오도에틸 등을 들 수 있다.Here, specific examples of iodoalkyl include iodomethyl, iodoethyl and the like.
한편, 상기 화학식 3으로 표시되는 화합물은 피롤과 포타슘 하이드라이드를 용매 존재 하에서 상온으로 1∼24시간 반응시켜 현탁액으로 얻을 수 있다.On the other hand, the compound represented by the formula (3) can be obtained as a suspension by reacting pyrrole and potassium hydride at room temperature for 1 to 24 hours in the presence of a solvent.
이와같이 얻어진 알킬 브로모 도데카노에이트와 피롤염을 1∼5시간 동안 반응시킨 다음, 반응용액에 물을 첨가하여 부산물로 생성되는 포타슘 브로마이드와 불순물을 녹이고, 여기에 다이에틸 에테르를 넣어 교반시킨다. 층분리가 일어난 용액을 분액깔때기에 넣고, 상층에 존재하는 다이에틸 에테르 층만을 추출하여 상온에서 6∼24시간 동안 건조시키면 화학식 1로 표시되는 함피롤 화합물 중에서 M이 에스테르기를 갖는 화합물인 화합물을 제조할 수 있다.The alkyl bromo dodecanoate thus obtained is reacted with the pyrrole salt for 1 to 5 hours, and then water is added to the reaction solution to dissolve potassium bromide and impurities formed as by-products, and the mixture is stirred with diethyl ether. Put the solution which separated the layer into a separatory funnel, extract only the diethyl ether layer present in the upper layer and dry for 6 to 24 hours at room temperature to prepare a compound in which M is a compound having an ester group in the hampyrrole compound represented by the formula (1) can do.
이어서, 얻어진 함피롤 화합물과 산 수용액을 25∼50℃에서 환류시켜 애시드화시키면 화학식 1로 표시되는 함피롤 화합물 중에서 M이 카르복실기인 화합물을 제조할 수 있다. 이때, 산으로는 염산, 황산, 질산 등을 사용할 수 있으나, 이에 한정되는 것은 아니다.Subsequently, when the obtained hampyrrole compound and the acid aqueous solution are refluxed at 25 to 50 ° C. for acidification, a compound in which M is a carboxyl group can be produced in the hampyrrole compound represented by the formula (1). In this case, hydrochloric acid, sulfuric acid, nitric acid, etc. may be used as the acid, but is not limited thereto.
이하, 본 발명을 실시예에 의거 상세히 설명하면 다음과 같은 바, 본 발명이 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited by the Examples.
제조예 1: 메틸브로모 도데카노에이트의 제조Preparation Example 1 Preparation of Methylbromo Dodecanoate
냉각기가 부착된 2구 플라스크에 12-브로모도데카노익 애시드 2g 및 요오도메탄 4.97㎖, 탄산 칼슘 9.75g, 아세톤 40㎖를 넣은 후 57℃에서 6시간 환류시킨 후, 반응용액을 필터링하여 탄산칼슘을 걸러냈다. 거른 용액은 다시 아세톤의 끓는점 하에서 아세톤을 증류시킨 후, 남은 잔여물에 메틸렌 클로라이드와 1노르말 농도의 수산화나트륨 수용액을 각각 30㎖ 넣고 교반하였다. 교반 후 두 층으로 분리된 용액을 분액 깔때기에 넣고 하층에 있는 메틸렌 클로라이드 층만을 추출하였다.추출한 메틸렌 클로라이드 용액에 황산 마그네슘을 0.8g 투입하여 건조, 여과한 후 메틸렌 클로라이드를 40℃에서 증류시켜 순수한 무색의 점성 액체인 메틸브로모 도데카노에이트를 얻었다.2 g of 12-bromododecanoic acid and 4.97 ml of iodomethane, 9.75 g of calcium carbonate, and 40 ml of acetone were added to a two-necked flask equipped with a cooler, and the mixture was refluxed at 57 ° C. for 6 hours. Calcium was filtered out. The filtered solution was distilled acetone under the boiling point of acetone again, and stirred with 30 ml each of methylene chloride and one-normal sodium hydroxide solution in the remaining residue. After stirring, the solution separated into two layers was placed in a separating funnel, and only the methylene chloride layer in the lower layer was extracted. 0.8 g of magnesium sulfate was added to the extracted methylene chloride solution, dried, filtered, and the methylene chloride was distilled at 40 ° C. to give pure colorlessness. Methyl bromo dodecanoate as a viscous liquid of was obtained.
제조예 2: 피롤염의 제조Preparation Example 2 Preparation of Pyrrole Salt
제조된 메틸브로모 도데카노에이트와 피롤의 결합을 용이하게 하기 위해 질소기류하 3구 플라스크에 테트라하이드로퓨란 30㎖, 포타슘 하이드라이드 0.3g, 피롤 0.4㎖(포타슘하이드라이드와 피롤의 반응비=1.1:1 질량비)을 투입하여 상온에서 4시간 반응시켜 현탁액의 피롤염을 제조하였다.30 mL of tetrahydrofuran, 0.3 g of potassium hydride, 0.4 g of pyrrole (reaction ratio of potassium hydride and pyrrole = 1.1 in a three-necked flask under nitrogen stream to facilitate the binding of the prepared methylbromo dodecanoate and pyrrole) 1 mass ratio) was added and reacted at room temperature for 4 hours to prepare a pyrrole salt of the suspension.
실시예 1Example 1
상기 제조예 1과 제조예 2에서 각각 제조된 메틸브로모 도데카노에이트와 피롤염을 플라스크에 넣고 8시간 반응시킨 후 반응용액에 물을 30㎖ 넣어 교반하였다. 층분리가 일어난 용액을 분액깔때기에 넣고, 상층에 존재하는 다이에틸 에테르 층만을 추출하여 상온에서 24시간 동안 건조시켜 다음 화학식 4와 같은 에스터기를 갖는 순수한 피롤릴 도데카노에이트를 합성하였다. 외관은 연한 노란빛을 띠는 점성 액체였다.Methyl bromo dodecanoate and pyrrole salt prepared in Preparation Example 1 and Preparation Example 2 were added to the flask and allowed to react for 8 hours, and 30 ml of water was added to the reaction solution and stirred. The separated solution was placed in a separatory funnel, and extracted only the diethyl ether layer present in the upper layer and dried at room temperature for 24 hours to synthesize a pure pyrrolyl dodecanoate having an ester group as shown in the following formula (4). The appearance was a pale yellowish viscous liquid.
실시예 2Example 2
상기 실시예 1에서 제조된 피롤릴 도데카노에이트 1g과 1N의 염산 수용액을30㎖ 투입하고, 50℃에서 환류시켰다. 반응용액에 다시 에틸 아세테이트 30㎖를 넣어 교반하였고, 층분리가 일어난 것을 확인한 후, 분액깔때기를 이용하여 에틸 아세테이트층만을 추출하였다. 추출한 에틸 아세테이트 용액은 40℃ 하에서 감압증류하여 에틸아세테이트를 제거하고, 다음 화학식 5로 표시되는 카르복실기를 갖는 12-피롤릴 도데카노익 애시드를 제조하였다. 외관은 연한 노란빛을 띠는 점성액체였다.30 g of 1 g of pyrrolyl dodecanoate and 1 N hydrochloric acid solution prepared in Example 1 was added thereto, and the mixture was refluxed at 50 ° C. 30 ml of ethyl acetate was added to the reaction solution, followed by stirring. After confirming that the separation of layers occurred, only the ethyl acetate layer was extracted using a separatory funnel. The extracted ethyl acetate solution was distilled under reduced pressure at 40 ° C. to remove ethyl acetate, and a 12-pyrrolyl dodecanoic acid having a carboxyl group represented by Formula 5 was prepared. Appearance was pale yellow viscous liquid.
상기 실시예 1로부터 얻어진 피롤릴 도데카노에이트(a)와 실시예 2로부터 얻어진 12-피롤릴 도데카노익 애시드(b)의 적외선 흡수 스펙트럼을 도 1에 나타내었다.Infrared absorption spectra of the pyrrolyl dodecanoate (a) obtained in Example 1 and the 12-pyrrolyl dodecanoic acid (b) obtained in Example 2 are shown in FIG. 1.
실험예Experimental Example
Langumir-Blagett 기법을 이용하여 전개용액으로서 상기 실시예 1 내지 2로부터 얻어진 각각의 화합물을 벤젠에 녹여 1.5mM의 농도로 하여 그 용액으로 LB 유기 초박막을 제조하여 전기전도도를 측정하였다.Using the Langumir-Blagett technique, each compound obtained in Examples 1 to 2 as a developing solution was dissolved in benzene to a concentration of 1.5 mM, and an LB organic ultra thin film was prepared from the solution, and electrical conductivity was measured.
비교예 1로는 일반적인 피롤을 전기중합에 의해 폴리아크릴로 나이트릴과 공중합시킨 고분자를 가지고, 스핀 코팅의 방법으로 박막을 제조한 후 전기전도도를 측정하였다.In Comparative Example 1, a polymer obtained by copolymerizing general pyrrole with polyacrylonitrile by electropolymerization was prepared, and a thin film was manufactured by spin coating, and electrical conductivity was measured.
비교예 2로는 지방산염인 아라키딕 애시드를 가지고 매트리스 LB 유기초박막을 제조한 후, 피롤을 다층막 내부로 도입시켜 복합체로 만든 물질을 이용하여 전기전도도를 측정하였다.In Comparative Example 2, after preparing a mattress LB organic ultrathin film having an arachidic acid which is a fatty acid salt, pyrrole was introduced into the multilayer film, and electrical conductivity was measured using a material made of a composite.
전기전도도의 측정은 멀티미터를 이용하여 2단자법을 사용하여 수행되었다.The conductivity measurement was performed using a two-terminal method using a multimeter.
그 결과는 다음 표 1에 나타낸 바와 같다.The results are shown in Table 1 below.
상기 표 1의 결과로부터, 일반적인 막의 제조방법으로 제조한 전도성 물질(비교예 1)에 비해 전도성 LB 유기초박막을 제조한 전도성 물질이 전도성이 더 우수하였고, 매트릭스를 이용한 전도성 LB 유기초박막(비교예2)보다는 본 발명의 화학식 1로 표시되는 함피롤 화합물로 LB 유기초박막을 제조한 경우가 더 우수한 전도성을 나타냄을 알 수 있었다.From the results of Table 1 above, the conductive material prepared with the conductive LB organic ultrathin film was more conductive than the conductive material prepared by the general method for preparing the film (Comparative Example 1), and the conductive LB organic ultrathin film using the matrix (Comparative Example 2). It was found that when the LB organic ultrathin film was prepared with the hampyrrole compound represented by the formula (1) of the present invention, it showed better conductivity.
이상에서 상세히 설명한 바와 같이, 본 발명에 따라 얻어진 신규한 함피롤 화합물은 초박막을 제조하여 유기 전도체로 사용시 전자적 성질의 조절이 가능한 우수한 전도성을 가지며, 친수성기와 소수성을 동시에 지닌 안정한 화합물로서, LB 유기 초박막의 제조가 직접 가능하여 우수한 배향성과 더불어 기타 유기박막에 비해 한층 전도성을 높이는 효과가 있다.As described in detail above, the novel hampyrrole compound obtained in accordance with the present invention is a stable compound having a hydrophilic group and a hydrophobicity at the same time having an excellent conductivity that can control the electronic properties when used as an organic conductor by producing an ultra-thin film, LB organic ultra-thin film It is possible to directly manufacture of the excellent orientation and the effect of increasing the conductivity compared to other organic thin films.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020020021947A KR20030083778A (en) | 2002-04-22 | 2002-04-22 | Novel pyrrole compound and manufacturing method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020020021947A KR20030083778A (en) | 2002-04-22 | 2002-04-22 | Novel pyrrole compound and manufacturing method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20030083778A true KR20030083778A (en) | 2003-11-01 |
Family
ID=32379942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020020021947A KR20030083778A (en) | 2002-04-22 | 2002-04-22 | Novel pyrrole compound and manufacturing method thereof |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR20030083778A (en) |
-
2002
- 2002-04-22 KR KR1020020021947A patent/KR20030083778A/en not_active Application Discontinuation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1317275C (en) | Sulfoxide compound and complex of acetone, and production method thereof | |
| WO2007004437A1 (en) | SILVER β-KETOCARBOXYLATE, MATERIAL COMPRISING THE SAME FOR FORMING SILVER METAL, AND USE THEREOF | |
| JP4137583B2 (en) | Use of sulfonic, phosphonic and phosphoric acids as dopants for polyaniline and conductive polyaniline based composites | |
| CN101177392A (en) | Method for preparing 9,10-dihydroxystearic acid and its methyl by hydrogen dioxide oxidation process | |
| KR101292329B1 (en) | Preparation method of alkyllactate and process for preparing lactamide using the same | |
| KR20030083778A (en) | Novel pyrrole compound and manufacturing method thereof | |
| CN117088919B (en) | Catalyst for thiophene monomer polymerization and polythiophene | |
| JP4140792B2 (en) | Chlorosulfonic acid derivatives of cyclic phenol sulfides and process for producing the same | |
| CN101037445A (en) | Imidazo [2,1-b]-1,3,4-thiadiazole derivatives having potential biological activity and synthesizing method thereof | |
| CN114907278B (en) | Preparation method of acylhydrazone macrocyclic-based polymer | |
| CN112079765B (en) | Synthesis method of 1- [60] fullerene pyrrolidine derivative | |
| CN114133403B (en) | 9,9-bis (trifluoromethyl) -2,3,6,7-xanthene tetracarboxylic dianhydride synthesis method | |
| Agnes et al. | Crystal structure analyses facilitate understanding of synthesis protocols in the preparation of 6, 6′-dibromo-substituted BINOL compounds | |
| CN112142613B (en) | Rosin-based small-molecule organic gel and cyclohexane gel formed by same | |
| CN107337626A (en) | A kind of alkyl hydrosulfide functionalization aromatic carboxylic acids and preparation method thereof | |
| CN110229336B (en) | Di (polyoxometallate) -organic chain-cage type silsesquioxane hybrid cluster compound and preparation method thereof | |
| CN109734737B (en) | Preparation method and application of gem-diboron compound | |
| CN114989082B (en) | Efficient preparation method of hydroxychloroquine based on synergistic catalysis of I-valent copper compound and trisubstituted phosphine | |
| JP2007211138A (en) | Alicyclic polyether, its production method, and its use | |
| CN109761947A (en) | A kind of synthetic method being functionalized Benzochromene class compound | |
| CN114213440B (en) | 2-boron alkenyl oxygen ether compound and preparation method thereof | |
| CN104961714B (en) | Synthetic method of alpha,beta-unsaturated butyrolactone | |
| KR102663941B1 (en) | A method for manufacturing Drometrizole trisiloxane(DMTS) | |
| CN115960357B (en) | Vinyl T 8 ，T 10 And T 12 Macroscopic quantity separation method of POSS | |
| CN112457170B (en) | Preparation method of 2,2,4, 4-tetramethyl-1, 3-cyclobutanediol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |