KR20020058980A - Compound with two-photon absorption effect and the polymer therefrom - Google Patents
Compound with two-photon absorption effect and the polymer therefrom Download PDFInfo
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Abstract
Description
본 발명은 2광자 흡수현상을 나타내는 갖는 신규 화합물 및 이를 중합하여 제조한 폴리머에 관한 것이다.The present invention relates to a novel compound having a two-photon absorption phenomenon and a polymer prepared by polymerizing the same.
강한 레이저 하에서 어떤 분자들은 둘 또는 그 이상의 광자를 동시에 흡수하는 현상을 나타내는데, 이 중 두개의 광자를 흡수하는 성질을 2광자 흡수(two-photon absorption)현상이라 한다. 이러한 2광자 흡수현상을 나타내는 분자들은 옵티칼 리미팅(optical limiting), 3차원 형광 마이크로스코피(fluorescence microscopy), 3차원 초미세공정(sub-micro fabrication), 광정보저장(optical data storage)등에 응용될 수 있다. 최근 이러한 비선형성을 응용한 물질의 개발을 위하여 높은 흡광도를 지닌 분자들의 많은 개발이 있었으나 실질적으로 응용에 관계되는 단위 매질에 존재하는 이광자 흡수 분자의 농도를 증가 시켜줄 수 있는 물질의 합성에 있어서는 그 연구가 거의 없었다.Under a strong laser, some molecules absorb two or more photons simultaneously, of which two photons are called two-photon absorption. These two-photon absorption molecules can be applied to optical limiting, three-dimensional fluorescence microscopy, three-dimensional sub-micro fabrication, and optical data storage. have. Recently, there have been many developments of molecules with high absorbance for the development of materials applying such nonlinearity, but in the synthesis of materials that can increase the concentration of two-photon absorbing molecules in the unit medium, which is practically related to the application. There was almost no.
2광자 현상을 보이는 분자들은 실제 응용물질로 사용되어지기 위해서는 대부분의 경우에 있어서 폴리머에 도핑 되거나 폴리머의 펜던트 그룹(pendant group)의 형태로 존재하기 때문에 실제응용 되는 물질의 2광자 현상의 효율은 분자고유의 흡수계수 뿐만 아니라 2광자 화합물이 폴리머 내에 함유되는 농도에 또한 직접적인 영향을 받는다.Since the molecules showing two-photon phenomena are used in practical applications, in most cases they are doped into the polymer or exist in the form of pendant groups of the polymer, so the efficiency of the two-photon phenomenon of the applied material is In addition to the intrinsic absorption coefficient, the concentration of the two-photon compound in the polymer is also directly affected.
형광 분자가 폴리머 주사슬과 화학 결합으로 연결된 후자의 경우는 분산의 형태로 폴리머 내에 존재하는 전자의 경우에 비해 보다 많은 양의 형광체를 함유할 수 있는 장점을 지닌다. 그러나 대부분의 이러한 폴리머 주사슬과 형광 분자와의 공유 결합은 적당한 작용기를 가진 폴리머를 합성한 후에 형광체를 그 작용기와 반응시킴으로써 만들어지기 때문에 최대 형광체의 농도는 그 반응성에 의존하며 폴리머의 반응성 작용기가 형광체로 전환되는 데는 한계가 있었다.The latter case, in which fluorescent molecules are connected by polymer bonds with chemical bonds, has the advantage of containing larger amounts of phosphors than the former case present in the polymer in the form of dispersion. However, since most of these covalent bonds with polymer backbones and fluorescent molecules are made by synthesizing a polymer with a suitable functional group and then reacting the phosphor with its functional group, the maximum phosphor concentration depends on its reactivity and the reactive functional group of the polymer There was a limit to the transition.
2광자 현상을 보이는 분자들은 실제 응용물질로 사용되어지기 위해서는 대부분의 경우에 있어서 용매에 녹여지거나 폴리머에 도핑된 형태를 사용하고 있는데, 고형의 유-무기물에 이광자 흡수분자를 도핑시킨 예로서 에폭시와 복합유리에 BTDOT(2,5-benzothiazole 3,4-didodecyloxy thiophene) 를 도핑한 경우(Bruce A. Reinhard, Optics Communications 117권, pp.133-136, 1995년 5월)와 TAP(12-O-tetradecanoyl-phorbol-13-acetate) 분자인 ASPT(trans-4-[p-(N-ethyl-N-hydroxyethylamino)styryl)]-N-methylpyridinium tetraphenylborate)를 에폭시나 폴리(HEMA)에 분산시킨 경우(Prasas N. Prasad, Chem. Mater. 9권, p2921, 1997)등 다수의 시도가 이루어지고 있는데, 이 경우 실제응용 되는 물질의 2광자 현상의 효율은 분자고유의 흡수계수 뿐만 아니라 2광자화합물이 폴리머 내에 함유되는 농도에 또한 직접적인 영향을 받는다.In order to be used as a practical application material, the molecules showing the two-photon phenomenon are in most cases dissolved in a solvent or doped with a polymer. For example, epoxy and dopant absorbing molecules are doped with solid organic-inorganic materials. Doped BTDOT (2,5-benzothiazole 3,4-didodecyloxy thiophene) in composite glass (Bruce A. Reinhard, Optics Communications, Vol. 117, pp. 133-136, May 1995) and TAP (12-O- When the tetradecanoyl-phorbol-13-acetate molecule ASPT (trans-4- [p- (N-ethyl-N-hydroxyethylamino) styryl)]-N-methylpyridinium tetraphenylborate) is dispersed in epoxy or poly (HEMA) (Prasas N. Prasad, Chem. Mater. Vol. 9, p2921, 1997), and many attempts have been made. In this case, the efficiency of two-photon phenomena of the applied materials is not only due to the absorption coefficient of the molecular but also the two-photon compound in the polymer. The concentration contained is also directly affected.
특히, 용매에 녹여진 형태로 2광자 흡수 물질이 존재하는 경우에는 플럭츄에이션(fluctuation)에 의한 국부적인 농도의 변이가 주요 문제점으로 지적되며, 이러한 단점을 보강하기 위하여 2광자 흡수분자를 폴리머에 분산하여 사용하는 경우에는 메트릭스를 이루는 폴리머와 2광자 흡수분자와의 상용성이 중요한 인자로 작용하는데 상분리 현상에 의한 단분자의 응집(aggregate)현상과 시간이 지남에 따른 상분리현상으로 기대되는 기능의 저하 즉 수명의 저하 등이 주요 문제점으로 인식되고있다.In particular, when a two-photon absorbing material is present in a solvent, a variation in local concentration due to fluctuation is pointed out as a major problem, and in order to reinforce this disadvantage, the two-photon absorbing molecule is added to the polymer. In case of dispersion, compatibility between matrix polymer and two-photon absorbing molecule is an important factor. It is a function of agglomeration of single molecules due to phase separation and phase separation over time. Degradation, that is, deterioration of life, is recognized as a major problem.
이러한 상 분리현상을 극복하기 위하여, 적당한 작용기를 가진 폴리머와 2광자 흡수분자와의 반응을 통하여 제조하는 2광자 흡수분자를 나타내는 폴리머는 2광자 흡수효과를 나타내는 분자가 폴리머 주쇄에 화학결합에 의하여 연결되어 있기 때문에 2광자 흡수물질이 호스트 폴리머에 분산의 형태로 존재하여 폴리머와 흡수분자사이의 물리적 상호관계에 그 안정성을 근거하는 경우와 비교할 때 보다 향상된 안정성을 갖는다는 장점이 있다.In order to overcome this phase separation phenomenon, a polymer exhibiting a two-photon absorption molecule prepared through the reaction of a polymer having a suitable functional group and a two-photon absorption molecule is connected to a polymer main chain by a molecule having a two-photon absorption effect. As a result, the two-photon absorbing material is present in the form of dispersion in the host polymer, and thus has an improved stability compared with the case where the physical relationship between the polymer and the absorbing molecule is based on the stability thereof.
그러나 이 경우에 있어서도 2광자 흡수 물질이 폴리머의 펜던트 작용기와 반응되는 수율에는 한계가 있고 이 수율은 폴리머에 존재하는 2광자 흡수 물질의 농도를 결정하게 되므로, 이에 적합한 2광자 흡수 효과를 갖는 단량체를 합성하고 그 중합을 통하여 폴리머 내에 더욱 증가된 농도의 2광자 흡수물질을 갖도록 하는 연구가 진행되고 있다.However, even in this case, there is a limit to the yield of the two-photon absorbing material reacting with the pendant functional group of the polymer, and this yield determines the concentration of the two-photon absorbing material present in the polymer. Research has been conducted to synthesize and increase the concentration of two-photon absorbents in the polymer through the polymerization.
따라서 본 발명은 상기한바와 같은 문제점을 해결할 수 있는, 2광자 흡수 현상을 갖는 작용기를 펜던트 그룹 (pendant group)으로 하는 폴리머를 제공하여 단위 부피에서 나타나는 2광자 흡수와 여기된 (excited) 분자들의 발광현상을 극대할 수 있도록 하는 데에 그 목적이 있다.Accordingly, the present invention provides a polymer having a functional group having a two-photon absorption phenomenon as a pendant group, which can solve the problems as described above, thereby emitting two-photon absorption and excited light emitted from a unit volume. The purpose is to maximize the phenomenon.
이에 본 연구자들은 예의 연구를 거듭한 결과, 단위 부피 내에 존재하는 이광자 흡수 분자의 농도를 극대화 할 수 있도록 하는 신규한 이광자 흡수 단량체의 합성과 그 중합을 통한 폴리머를 합성하기에 이르렀다.As a result of intensive research, the researchers have synthesized a novel two-photon-absorbing monomer that can maximize the concentration of two-photon-absorbing molecules in a unit volume and synthesized a polymer through the polymerization.
본 발명은 하기 중합가능한 부분(Y)과 2광자 현상을 나타내는 작용기(X)가 Y-X로 연결된 화합물을 제공한다.The present invention provides a compound in which a polymerizable moiety (Y) and a functional group (X) exhibiting two-photon phenomenon are connected by Y-X.
상기 Y- 는 하기 화학식 1 내지 3 중 하나의 구조를 가지는 것이 바람직하다.It is preferable that Y- has a structure of one of the following Chemical Formulas 1-3.
상기 식에서, n은 0 내지 3의 정수임.Wherein n is an integer from 0 to 3.
상기 식에서, n은 0내지 3의 정수, R1은 H 또는 CH3임.Wherein n is an integer from 0 to 3 and R 1 is H or CH 3 .
상기 식에서, R2는 CH2,S,O,Se,NR3(R3는 알킬 또는 페닐기)중 하나임.Wherein R 2 is one of CH 2 , S, O, Se, NR 3 (R 3 is an alkyl or phenyl group).
또한 상기 -X 는 하기 화학식 4의 구조를 갖는 것이 바람직하다.In addition, the -X preferably has a structure represented by the following formula (4).
상기 식에서, A는 OR, SR, CN, CO2, NR4R5(R4및 R5는 각각 알킬 또는 페닐기) 중 선택된 하나이고, m은 0 내지 3의 정수이다.Wherein A is one selected from OR, SR, CN, CO 2 , NR 4 R 5 (R 4 and R 5 are each alkyl or phenyl group), and m is an integer from 0 to 3.
본 발명은 또한 상기 화합물(Y-X)를 중합시켜 Y부분은 폴리머 주사슬을 형성하고, 상기 X부분은 펜던트 형태로 연결된 구조를 갖는 하기 화학식 5의 구조를 갖는 폴리머를 제공한다.The present invention also polymerizes the compound (Y-X) to provide a polymer having a structure of Formula 5 having a structure in which the Y moiety forms a polymer main chain and the X moiety is linked in a pendant form.
상기한 바와 같이 본 발명에서 제공하는 화합물은 중합이 가능한 부분(Y)과 2광자 흡수효과를 나타내는 부분(X)의 두 부분을 모두 포함하고 있다. 2광자 흡수효과를 나타내는 부분은As described above, the compound provided in the present invention includes both the moiety (Y) and the moiety (X) having a two-photon absorption effect. The part showing two-photon absorption effect
(1) 전자주게 - π전자중심체 - 전자주게,(1) Electron donor-π electron core-electron donor,
(2) 전자주게 - π전자중심체 - 전자받게; 및(2) electron donor-π electron core-electron acceptor; And
(3) 전자받게 - π전자중심체 - 전자받게의 세가지 구조로 나눌 수 있다. 이와 같은 구조에서 전자주게 부분은 에테르, 싸이오 에테르, 아민 등이 될 수 있으며, 전자받게부분은 나이트릴, 카보닐기 등이 될 수 있다.(3) electron acceptor-π electron core-It can be divided into three structures. In such a structure, the electron donor portion may be an ether, a thio ether, an amine, or the like, and the electron acceptor portion may be a nitrile, a carbonyl group, or the like.
또한 상기 π전자중심체부분은 벤젠, 테오펜, 스틸벤, 아조 단위의 조합된 구조들이 될 수 있으나, 특히 스틸벤의 구조인 경우에 폴리머에 연결되어 상기 화학식 4의 구조를 가지게 된다.In addition, the π electron core portion may be a combination structure of benzene, theophene, stilbene, and azo units, but in the case of the structure of stilbene, it is connected to a polymer to have the structure of Chemical Formula 4.
X를 구성하는 부분은 불포화 비닐기의 스타이렌계(상기 화학식 1), 아크릴계(상기 화학식 2), 메타아크릴계(상기 화학식 3)와 개환중합으로 폴리머를 만들어 낼 수 있는 바이시클릭 단량체(상기 화학식 4)등을 부가중합형태로 합성하여 제조할 수 있다.The part constituting X is a bicyclic monomer (Formula 4) capable of producing a polymer by styrene-based (Formula 1), acrylic (Formula 2), methacryl-based (Formula 3) and ring-opening polymerization of an unsaturated vinyl group. ) Can be prepared by synthesizing in an addition polymerization form.
상기 화학식 1 및 2를 보면, 2광자 흡수효과를 나타내는 부분이 연결될 부분이 포화알킬기임을 알 수 있는데, 이 알킬기의 길이에 따라 2광자 흡수 현상을 나타내는 부분이 폴리머 내에서 패킹되는 현상이 영향을 받게 된다.In the above formulas (1) and (2), it can be seen that the part to which the part showing the two-photon absorption effect is connected is a saturated alkyl group, and the phenomenon in which the part showing the two-photon absorption phenomenon is packed in the polymer is affected by the length of the alkyl group. do.
2광자 흡수 현상을 나타내는 부분은 상기한 바와 같이 전자이동의 다리역할을 하는 π전자중심체 즉, 방향족이나 불포화 탄화수소가 결합된 부분으로 연결되어 있으며, 전자주게(donor) 또는 전자받게(acceptor)에 의해 치환된 형태, 즉 샌드위치된 모양의 구조를 갖는다.The part showing the two-photon absorption phenomenon is connected to the π electron core which acts as a bridge of electron transfer as described above, that is, a portion in which an aromatic or unsaturated hydrocarbon is bound, and is connected by an electron donor or an electron acceptor. It has a substituted form, that is, a sandwiched structure.
상기 화학식 4에서 볼 수 있듯이 X 부분은 m 값을 변화시켜 줌에 따라 결합(conjugation)정도를 조절하여 줄 수 있다. 전자주게 부분에는 알킬 또는 방향족과 연결된 에테르기나 아민기가 올 수 있다.As can be seen in Formula 4, the X part can adjust the degree of conjugation as the value of m is changed. The electron donor portion may be an ether group or an amine group linked with an alkyl or aromatic group.
이하 본 발명에 따른 화합물 및 폴리머의 제조방법 및 실시예을 통하여 본 발명을 좀 더 상세히 설명하기로 한다.Hereinafter, the present invention will be described in more detail with reference to methods and examples of preparing compounds and polymers according to the present invention.
우선, 스타이렌계, 아크릴계, 메타아크릴계의 단량체를 사용하는 경우는 유기금속(organometallic) 개시제를 이용한 음이온 중합이나 일반적인 라디컬중합방법으로 상기 화학식 1 및 화학식 2을 합성한다.First, in the case of using styrene-based, acryl-based, or methacryl-based monomers, Chemical Formulas 1 and 2 are synthesized by anionic polymerization using an organometallic initiator or a general radical polymerization method.
실시예 1)Example 1
상기 화학식 1의 화합물을 이용하여 음이온 중합 개시제로 부틸리튬을 사용하여 벤젠 또는 사이클로헥산 용매하에서 중합하였다. 이러한 중합에 사용된 용매와 단량체는 정제 후 인디케이터가 있는 플라스크에 보관하였고, 중합은 아르곤 하에서 이루어졌다. 이광자 흡수 효과를 나타내는 부분이 시안기나 나이트로기로 치환된 경우는 음이온중합을 사용하지 않았다.The compound of Formula 1 was used to polymerize in a benzene or cyclohexane solvent using butyllithium as an anionic polymerization initiator. Solvents and monomers used for this polymerization were stored in flasks with indicators after purification, and polymerization was carried out under argon. When the part showing the two-photon absorption effect was substituted with a cyan group or a nitro group, anion polymerization was not used.
실시예 2)Example 2)
상기 화학식 2의 화합물을 음이온 중합방법으로 중합하기 위하여 -78℃에서 THF(테트라하이드로퓨란) 용매에 부틸리튬과 디페닐에틸렌을 동일한 몰비로 넣은 후 단량체를 반응용액에 부가하였다. 중합은 상기 실시예1 과 같이 아르곤 하에서 이루어졌다. 원하는 분자량이 얻어질 때까지 교반한 후 메탄올을 반응용액에 넣어 줌으로써 중합을 종결시켰다.In order to polymerize the compound of Chemical Formula 2 by anionic polymerization, butyllithium and diphenylethylene were added to THF (tetrahydrofuran) solvent at -78 ° C. in the same molar ratio, and monomers were added to the reaction solution. The polymerization was carried out under argon as in Example 1 above. After stirring until the desired molecular weight was obtained, polymerization was terminated by adding methanol to the reaction solution.
이렇게 상기 실시예 1) 및 2)에서 얻어진 결과물에서 과량의 용매를 제거한 후, 메탄올에 침전시켜 용매를 제거하고 폴리머를 건조시켜 분말 상태로 보관하였다. 필요에 따라서 폴리머를 THF에 다시 녹이고 메탄올로 침전 시키는 과정을 세 번 정도 반복할 수도 있다.Thus, excess solvent was removed from the resultant obtained in Examples 1) and 2), and then precipitated in methanol to remove the solvent, and the polymer was dried and stored in powder form. If necessary, the process of dissolving the polymer in THF and precipitating with methanol may be repeated three times.
실시예 3) 화학식 3의 화합물의 합성Example 3) Synthesis of Compound of Formula 3
바이시클릭 단량체를 그랍스(Grubbs's) 촉매를 이용하여 개환복분해중합 (Ring Opening Metathesis Polymerization; ROMP)방법을 이용하여 중합하였다. 바이시클릭 단량체의 그랍스(Grubbs's) 촉매에 의한 개환 중합은 아르곤 하에서 모노머용액을 얼린 후 진공을 걸어주고 다시 아르곤을 주입시키고 용액을 녹이는 일련의 과정을 세번 되풀이 한 후, 원하는 분자량에 맞는 량의 촉매를 반응용액에 주입시켜서 중합을 하는 슐랭크 기법(Schlenk technique)을 이용하였다(Grubbs 등., Macromolecules, 1993, 26, 4975.) 얻어진 결과물을 메탄올에 침전시킨 후 건조하여 분말의 폴리머를 얻었다.Bicyclic monomers were polymerized using a Ring Opening Metathesis Polymerization (ROMP) method using Grubbs's catalyst. The ring-opening polymerization of the bicyclic monomer by Grubbs's catalyst is performed by freezing the monomer solution under argon, applying vacuum, injecting argon and dissolving the solution three times, and then The Schlenk technique was used to inject the catalyst into the reaction solution and polymerize (Grubbs et al., Macromolecules, 1993, 26, 4975.). The resultant was precipitated in methanol and dried to obtain a powdery polymer.
본 발명에 따른 2광자 흡수 효과를 갖는 화합물과 이를 펜던트 그룹(pendant group)으로 하는 폴리머에 의하여 단위 부피에서 나타나는 2광자 흡수와 여기된(excited) 분자들의 발광현상을 극대화할 수 있어, 2광자 분자들의 응용을 더욱 실용적으로 성취하는 효과를 갖게된다. 또한 폴리머 매트릭스내에 존재하는 2광자 흡수 물질의 농도를 증가시킬 수 있고, 매질을 구성하는 물질과 2광자 흡수작용기를 공유결합으로 연결함으로써 시간이 지남에 따라 일어나는 상분해 현상에 의한 2광자 흡수현상의 저하를 피하여 2광자 흡수현상을 이용한 응용물질의 수명을 증가시키게 된다.The compound having a two-photon absorption effect according to the present invention and a polymer having a pendant group thereof can maximize two-photon absorption and excited light emission of excited molecules. Will have the effect of achieving their application more practical. In addition, it is possible to increase the concentration of two-photon absorbing material present in the polymer matrix, and the two-photon absorption phenomenon due to the phase decomposition phenomenon that occurs over time by covalently connecting the material constituting the medium and the two-photon absorbing functional group. Avoiding degradation increases the lifetime of the application material using two-photon absorption.
또한 2광자 흡수분자상호간에 완충(buffer)역할을 하는 유기물질을 삽입하게 됨으로써 2광자 흡수분자간 간격이 가까울 때 발생하는 분자간의 상호간섭(cross talk)에 의한 2광자 흡수계수의 저하현상을 조절하여 실질적인 2광자 현상이 증가된다.In addition, by inserting an organic material that acts as a buffer between the two-photon absorption molecules, it is possible to control the degradation of the two-photon absorption coefficient due to cross talk between molecules generated when the two-photon absorption molecules are close to each other. The actual two photon phenomenon is increased.
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| WO1998021521A1 (en) * | 1996-11-12 | 1998-05-22 | California Institute Of Technology | Two-photon or higher-order absorbing optical materials and methods of use |
| US5912257A (en) * | 1995-09-06 | 1999-06-15 | The Research Foundation Of State University Of New York | Two-photon upconverting dyes and applications |
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| US5912257A (en) * | 1995-09-06 | 1999-06-15 | The Research Foundation Of State University Of New York | Two-photon upconverting dyes and applications |
| WO1998021521A1 (en) * | 1996-11-12 | 1998-05-22 | California Institute Of Technology | Two-photon or higher-order absorbing optical materials and methods of use |
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| Opt.Comm., Guang S. He, 117, pp 133-136, 1995 * |
| Opt.Lett., Guang S. He, 20(18), pp 435-437, 1995 * |
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| KR100466545B1 (en) * | 2002-02-19 | 2005-01-15 | 한국전자통신연구원 | Method for manufacturing polymer nano particle |
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