JPH0290130A - Organic nonlinear optical material - Google Patents
Organic nonlinear optical materialInfo
- Publication number
- JPH0290130A JPH0290130A JP24305488A JP24305488A JPH0290130A JP H0290130 A JPH0290130 A JP H0290130A JP 24305488 A JP24305488 A JP 24305488A JP 24305488 A JP24305488 A JP 24305488A JP H0290130 A JPH0290130 A JP H0290130A
- Authority
- JP
- Japan
- Prior art keywords
- nonlinear optical
- single crystal
- stable
- shg
- crystal
- 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.)
- Granted
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 34
- 239000000463 material Substances 0.000 title claims abstract description 27
- AMHFUIBAMYJKRL-UHFFFAOYSA-N 4-[2-(4-nitrophenyl)ethenyl]benzaldehyde Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=CC1=CC=C(C=O)C=C1 AMHFUIBAMYJKRL-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000013078 crystal Substances 0.000 abstract description 35
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 4
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 abstract description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract description 3
- 235000021286 stilbenes Nutrition 0.000 abstract description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 abstract description 2
- 238000001704 evaporation Methods 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 230000001965 increasing effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- OBPVXJVFAMDMDQ-UHFFFAOYSA-N 4-[2-(4-nitrophenyl)ethynyl]benzaldehyde Chemical compound C1=CC([N+](=O)[O-])=CC=C1C#CC1=CC=C(C=O)C=C1 OBPVXJVFAMDMDQ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000002250 progressing effect Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YBADLXQNJCMBKR-UHFFFAOYSA-M (4-nitrophenyl)acetate Chemical compound [O-]C(=O)CC1=CC=C([N+]([O-])=O)C=C1 YBADLXQNJCMBKR-UHFFFAOYSA-M 0.000 description 1
- RYJATPLJVSILLB-UHFFFAOYSA-N 1-nitro-2-(2-phenylethenyl)benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1C=CC1=CC=CC=C1 RYJATPLJVSILLB-UHFFFAOYSA-N 0.000 description 1
- -1 2-(4-nitrophenyl)ethynyl Chemical group 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229920000015 polydiacetylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は、有機非線形光学材料に関し、さらに詳しくは
、光コンピュータや光通信など広範な分野で光制御素子
として用いることができる４−［２−（４−ニトロフェ
ニル）エチニル］ベンズアルデヒドから成る有機非線形
光学材料番こ関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to organic nonlinear optical materials, and more specifically, 4-[2 An organic nonlinear optical material comprising -(4-nitrophenyl)ethynyl]benzaldehyde.
〈従来の技術〉
非線形光学材料は、レーザー光の周波数変換、増幅、発
振、スイッチングなどの現象を生じ、第２高調波発生（
ＳＨＧ＞、第３高調波発生（ＴＨＧ）、高速度シャッタ
ー、光メモリ−、光演算素子などへの応用が可能である
。<Prior art> Nonlinear optical materials cause phenomena such as frequency conversion, amplification, oscillation, and switching of laser light, and generate second harmonics (
SHG>, third harmonic generation (THG), high-speed shutter, optical memory, optical arithmetic element, etc.
このように、非線形光学材料は、光周波数を変換する機
能を有しているほか、電場によって屈折率が変化する特
質を生かした光スィッチなどへの応用が可能であるため
、活発な研究が進められている。In this way, nonlinear optical materials have the function of converting optical frequencies and can be applied to optical switches that take advantage of the property that the refractive index changes depending on the electric field, so active research is progressing. It is being
従来、非線形光学材料としては、主として水溶性のＫＨ
１ＰＯ４（ＫＤＰ）、ＮＨ４Ｈｚ ＰＯ４あるいは非水
溶性のＬｉＮｂ０．、ＫＮｂＯｓなどの無機系の単結晶
材料（誘電体結晶）が用いられてきたが、最近は尿素や
ｐ−ニトロアニリン、２−メチル−４−ニトロアニリン
（ＭＮＡ）、４′−（Ｎ、Ｎ’−ジメチルアミノ）−４
−ニトロスチルベン（ＤＡＮＳ）などの有機非線形光学
材料の開発が進められている。ポリジアセチレンやポリ
フッ化ビニリデンなどの高分子有機材料についても、そ
の非線形光学効果を利用して、制御機能を有する導波路
、光ＩＣなどへの応用が検討されている。Conventionally, water-soluble KH has mainly been used as a nonlinear optical material.
1PO4 (KDP), NH4Hz PO4 or water-insoluble LiNb0. , KNbOs, and other inorganic single crystal materials (dielectric crystals) have been used, but recently urea, p-nitroaniline, 2-methyl-4-nitroaniline (MNA), '-dimethylamino)-4
- Development of organic nonlinear optical materials such as nitrostilbene (DANS) is progressing. Polymeric organic materials such as polydiacetylene and polyvinylidene fluoride are also being considered for application to waveguides with control functions, optical ICs, etc. by utilizing their nonlinear optical effects.
有機非線形光学材料は、非線形性の起源が分子内圧電子
であるため、光応答に対して格子振動を伴わず、したが
って無機材料に比べ応答が速く。In organic nonlinear optical materials, the origin of nonlinearity is intramolecular piezoelectrons, so there is no lattice vibration in response to light, and therefore the response is faster than inorganic materials.
また、非線形光学定数が大きいものや吸収領域が変化で
きるものなどを合成することが可能である。しかも、材
料素子化の方法も、単結晶化によるだけではなく、ＬＢ
膜、蒸着法、液晶化、高分子化などの各種の方法が考え
られる。Furthermore, it is possible to synthesize a material with a large nonlinear optical constant or a material whose absorption region can be changed. Moreover, the method of making materials into devices is not only based on single crystallization, but also on LB
Various methods can be considered, such as film formation, vapor deposition, liquid crystal formation, and polymerization.
これら非線形光学材料の研究に関しては、例えば、「有
機非線形光学材料Ｊ加藤政雄、中西へ部監修（シー・エ
ム・シー社、１９８５年刊）。Regarding research on these nonlinear optical materials, see, for example, "Organic Nonlinear Optical Materials J, supervised by Masao Kato and He Nakanishi Department (CMC Publishing Co., Ltd., 1985).
ｒＮｏｎｌｉｎｅａｒ ０ｐｔｉｃａｌ Ｐｒｏｐｅｒ
ｔｉｅｓ ｏｆ Ｏｒｇａｎｊ、ｃＭｏｌｅｃｕｌｅｓ
ａｎｄ Ｃｒｙｓｔａｌｓ Ｖｏｌ、 Ｉ及び Ｖ
ｏｌ、ｒｌＤ、Ｓ、ＣＩｌεＭＬＡ、 、Ｊ、 ＺＹＳ
Ｓ編（ＡＣＡＤＥＭＩＣＰＲＥＳＳ、１９８７年刊）な
どの文献に最近の研究状況がまとめられている。rNonlinear 0ptical Proper
ties of Organj, cMolecules
and Crystals Vol, I and V
ol,rlD,S,CIlεMLA, ,J,ZYS
Recent research status is summarized in documents such as Volume S (Academic Press, published in 1987).
ところで、非線形光学材料として要求される非線形光学
効果のうち、特に第２高調波発生（ＳＨＧ）は、変換の
効率が高い等の理由から波長変換の基本技術として位置
付けられている。また、効率よ＜ ＳＨＧをおこすため
に有効非線形光学定数の大きい材料が求められている。By the way, among the nonlinear optical effects required for nonlinear optical materials, second harmonic generation (SHG) in particular is positioned as a basic technology for wavelength conversion because of its high conversion efficiency. In addition, materials with large effective nonlinear optical constants are required in order to generate SHG with efficiency.
そして、先の文献に詳しく述べられているように、Ｓ
ＨＧ活性を示すためには結晶が対称中心を持たないこと
が必要である。And, as detailed in the previous literature, S
In order to exhibit HG activity, it is necessary for the crystal to have no center of symmetry.
非線形光学無機材料は一般に結晶性が良く、大きな結晶
を得やすいという性質があるが、有機材料に比較して非
線形光学定数が小さいという欠点がある。一方、非線形
光学有機材料には一般に非線形光学定数の大きいものが
あることは知られているが、室温で安定かつ大きな有機
結晶を調製するのが困難である。Nonlinear optical inorganic materials generally have good crystallinity and are easy to obtain large crystals, but they have the disadvantage of having smaller nonlinear optical constants than organic materials. On the other hand, although it is known that some nonlinear optical organic materials generally have large nonlinear optical constants, it is difficult to prepare stable and large organic crystals at room temperature.
例えば、従来知られている有機結晶の内、ＭＮＡは対称
中心を持たない結晶となるためＳＨＧ活性を有し、第２
高調波発生効率はＬ ｉ Ｎ ｂ Ｏｓの約２０００倍
もあることが報告されている。しかし、ＭＮＡは大きな
単結晶が得られにくいため実用的ではないという欠点が
ある。また、尿素は、大きな単結晶を得やすいけれども
、Ｓ ＨＧ活性が低く、また耐湿性に劣るという欠点が
ある。ＤＡＮＳは、分子レベルでは分子分極率βは非常
に大きい値を示すが、結晶になるとき対称中心を持つた
めに有機結晶ＤＡＮＳはＳＨＧを活性を示さない。For example, among conventionally known organic crystals, MNA has SHG activity because it is a crystal without a center of symmetry, and
It has been reported that the harmonic generation efficiency is about 2000 times that of L i N b Os. However, MNA has the disadvantage that it is difficult to obtain large single crystals, making it impractical. Further, although it is easy to obtain large single crystals from urea, it has the drawbacks of low SHG activity and poor moisture resistance. DANS exhibits a very large value of molecular polarizability β at the molecular level, but organic crystal DANS does not exhibit SHG activity because it has a center of symmetry when crystallized.
そこで、対称中心を持たない単結晶を形成し、有効非線
形光学定数が太き（、したがってＳＨＧ活性が大きい有
機非線形光学材料の開発が現在最も要求されているとこ
ろである。さらに、非線形光学材料として実用化するに
当たっては、室温で安定でかつ出来るだけ大きな単結晶
を形成するものであることが望まれる。しかしながら、
Ｓ ＨＧ活性が太き（、安定で、大きな単結晶に成長さ
せやすい有機非線形光学材料は未だ提供されていない。Therefore, the current greatest need is to develop an organic nonlinear optical material that forms a single crystal without a center of symmetry and has a large effective nonlinear optical constant (and therefore a large SHG activity). It is desirable that the crystal be stable at room temperature and form a single crystal as large as possible.However,
An organic nonlinear optical material with a large SHG activity, stable, and easy to grow into a large single crystal has not yet been provided.
〈発明が解決しようとする課題〉
本発明の目的は、前記従来技術の有する問題点を克服し
、室温で安定で、しかも対称中心を持たない単結晶を形
成し、必要に応じて大きな単結晶に成長°させることが
できるＳＨＧ活性の大きな有機非線形光学材料を提供す
ることにある。<Problems to be Solved by the Invention> The purpose of the present invention is to overcome the problems of the prior art described above, to form a single crystal that is stable at room temperature and has no center of symmetry, and to form a large single crystal as necessary. The object of the present invention is to provide an organic nonlinear optical material with high SHG activity that can be grown at high temperatures.
本発明者らは鋭意研究した結果、特定のスチルベン誘導
体がＳＨＧ活性の大きな有機結晶を形成することを見出
し、その知見に基づいて本発明を完成するに至った。As a result of intensive research, the present inventors discovered that a specific stilbene derivative forms organic crystals with high SHG activity, and based on this knowledge, they completed the present invention.
〈課題を解決するための手段〉
すなわち、本発明によれば、下記一般式で表される４−
（２−（４−ニトロフェニル）エチニルＪベンズアルデ
ヒドから成ることを特徴とする有機非線形光学材料が提
供される。<Means for solving the problem> That is, according to the present invention, 4- expressed by the following general formula
(2-(4-nitrophenyl)ethynyl J-benzaldehyde) An organic nonlinear optical material is provided.
以下、本発明の構成要素について詳述する。Hereinafter, the constituent elements of the present invention will be explained in detail.
本発明におけるスチルベン誘導体は、スヂルベン（ジフ
ェニルエチレンのトランス異性体）の各フェニル基にそ
れぞれホルミル基とニトロ基な有する構造を持っている
。The stilbene derivative in the present invention has a structure in which each phenyl group of stilbene (trans isomer of diphenylethylene) has a formyl group and a nitro group, respectively.
本発明のスチルベン誘導体は、結晶性が良好であり、有
機溶剤からスローエバポレイジョン法などにより容易に
単結晶を得ることができ、しかもその単結晶は室温で安
定である。The stilbene derivative of the present invention has good crystallinity, and a single crystal can be easily obtained from an organic solvent by a slow evaporation method or the like, and the single crystal is stable at room temperature.
また、本発明のスチルベン誘導体の単結晶は、尿素の約
２．５倍のＳＨＧ効率を示すことから明らかなように対
象中心を持たない単結晶である。Furthermore, the single crystal of the stilbene derivative of the present invention is a single crystal without a center of interest, as is clear from the fact that it exhibits an SHG efficiency about 2.5 times that of urea.
同じスチルベンの誘導体で、下記の構造式で表されるＤ
ＡＮＳは、大きな分子分極率を有するけれども、その有
機結晶が結晶の対称性のために有効非線形光学定数が０
．０でＳＨＧ活性を示さないことからみて、ポルミル基
を有する本発明のスチルベン誘導体が優れたＳ ＨＧ活
性を示す有機結晶を形成することは予期できないことで
ある。D, which is the same stilbene derivative and is represented by the structural formula below
Although ANS has a large molecular polarizability, its effective nonlinear optical constant is 0 due to the crystal symmetry of its organic crystal.
．． It is unexpected that the stilbene derivatives of the present invention having a polmyl group would form organic crystals exhibiting excellent SHG activity, considering that the stilbene derivatives of the present invention exhibit no SHG activity at zero.
本発明のスチルベン誘導体は、一方のフェニル基の４位
置くバラ位）に核置換基としてポルミル基を導入するこ
とによって、結晶の対称性を崩すことが可能になりＳ
ＨＧ活性が発現できるようになったと推察できる。In the stilbene derivative of the present invention, it is possible to break the symmetry of the crystal by introducing a polmyl group as a nuclear substituent at the 4-position (bar position) of one phenyl group.
It can be inferred that HG activity can now be expressed.
〈実施例〉
以下、実施例を挙げて本発明を具体的に説明するが、い
うまでもなく本発明はこれら実施例のみに限定されるも
のではない。<Examples> The present invention will be specifically described below with reference to Examples, but it goes without saying that the present invention is not limited to these Examples.
及將皿ユ＜４−［２−（４−ニトロフェニル）エチニル
］ベンズアルデヒドの合成〉
テレフタルアルデヒド６．０３ｇ （４５ミリモル）に
ｌ Ｏｍｊ２のジメチルホルムアミド（Ｄ ＭＦ）を加
えて溶液にした。その溶液にｐ−ニトロフェニル酢駿２
゜７２ｇ（１５ミリモル）のＤＭＦ溶液約４０ｍｊ２を
撹拌しながら室温にて徐々に滴下した。その後１００℃
まで油浴にて昇温し。<Synthesis of 4-[2-(4-nitrophenyl)ethynyl]benzaldehyde> To 6.03 g (45 mmol) of terephthalaldehyde was added 1 Omj2 of dimethylformamide (DMF) to form a solution. Add 2 p-nitrophenyl acetate to the solution.
About 40 mj2 of a DMF solution containing 72 g (15 mmol) was gradually added dropwise at room temperature while stirring. Then 100℃
Heat in an oil bath to .
２時間撹拌した。放論した後、この溶液を分液ロー１・
に移し、１．５０ ｍ℃のクロロホルムとＩＮの塩酸５
０ｍｇを加えて分液操作を行った。得られたクロロホル
ム層を無水硫酸ナトリウムにより乾燥した後、溶媒を留
去した。オイル状の生成物に水を加えると黄色の沈殿が
生成した。この沈殿物を濾過し、温水で洗浄して乾燥し
た。粗生成物は３．０６ｇであった。粗生成物をクロロ
ホルム−メタノールにより再結晶して目的物２．５４ｇ
を得た。Stirred for 2 hours. After stirring, transfer this solution to separation row 1.
Transfer to 1.50 mC of chloroform and IN hydrochloric acid 5
0 mg was added and a liquid separation operation was performed. After drying the obtained chloroform layer with anhydrous sodium sulfate, the solvent was distilled off. When water was added to the oily product, a yellow precipitate formed. The precipitate was filtered, washed with warm water and dried. The crude product was 3.06g. The crude product was recrystallized from chloroform-methanol to obtain 2.54 g of the desired product.
I got it.
この化合物の融点は２１８〜２２０℃であった。The melting point of this compound was 218-220°C.
この化合物の赤外線吸収スペクトル（ＩＲ）および核磁
気共鳴吸収スペクトル（’Ｈ−ＮＭＲ）を測定したとこ
ろ、特性スペクトルは次のとおりであり、４− （２−
（４−ニトロフェニル）エチニル］ベンズアルデヒドの
得られたことが確認された。When the infrared absorption spectrum (IR) and nuclear magnetic resonance absorption spectrum ('H-NMR) of this compound were measured, the characteristic spectrum was as follows.
It was confirmed that (4-nitrophenyl)ethynyl]benzaldehyde was obtained.
Ｉ Ｒ： １６９０．１６００．１５００．１３３０
．８５０ ［ｃｍ−’］Ｈ−Ｎ Ｍ Ｒ（ｃｏｃ＋、
） ：ｌＯ，１（Ｓ、 ＬＨ）、８．５３〜７．６０（
ｍ、８）１）、７．３７ （ｄ、 ２＋＋） ［δ（ｐ
ｐｍ）］上記の合成により得られた４−［２−（４−二
トロフェニル）エチニル］ベンズアルデヒドの微粉末結
晶をＮｄ：ＹＡＧレーザ−（波長＝１．０６４μｍ、出
力１０ｍＪ／パルス）で照射すると第２高調波が発生し
く５ＨＧ）、入射光の１／２の波長（５３２ｎｍ）の緑
色光が観測できた。IR: 1690.1600.1500.1330
．． 850 [cm-']H-NMR(coc+,
) :lO,1(S, LH), 8.53~7.60(
m, 8) 1), 7.37 (d, 2++) [δ(p
pm)] When the fine powder crystal of 4-[2-(4-nitrophenyl)ethynyl]benzaldehyde obtained by the above synthesis is irradiated with a Nd:YAG laser (wavelength = 1.064 μm, output 10 mJ/pulse), A second harmonic was generated (5HG), and green light with a wavelength of 1/2 of the incident light (532 nm) could be observed.
また、上記微結晶の第２高調波発生（ＳＨＧ）効率は、
尿素のそれを１とすると２．５であり、ＳＨＧ効率は尿
素よりもはるかに強いことが確認できた。In addition, the second harmonic generation (SHG) efficiency of the above microcrystal is
If the value of urea is 1, it is 2.5, and it was confirmed that the SHG efficiency is much stronger than that of urea.
さらに、この結晶は、室温で安定であり、結晶性の良い
ことも明らかになった。Furthermore, it was revealed that this crystal is stable at room temperature and has good crystallinity.
〈発明の効果〉
本発明の４− ［２−（４−ニトロフェニル）エチニル
］ベンズアルデヒドから成る有機非線形光学材料は、室
温で安定な単結晶を形成し、大きな５）（Ｇ活性を示す
ため、光制御素子などとして広範な分野で用いることが
できる。<Effects of the Invention> The organic nonlinear optical material comprising 4-[2-(4-nitrophenyl)ethynyl]benzaldehyde of the present invention forms a stable single crystal at room temperature and exhibits large 5)(G activity). It can be used in a wide range of fields, such as as a light control element.
Claims (1)
］ベンズアルデヒドから成ることを特徴とする有機非線
形光学材料。(1) An organic nonlinear optical material characterized by comprising 4-[2-(4-nitrophenyl)ethenyl]benzaldehyde represented by the following general formula ▲ Numerical formula, chemical formula, table, etc. ▼.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24305488A JPH07111529B2 (en) | 1988-09-27 | 1988-09-27 | Organic nonlinear optical material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24305488A JPH07111529B2 (en) | 1988-09-27 | 1988-09-27 | Organic nonlinear optical material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0290130A true JPH0290130A (en) | 1990-03-29 |
| JPH07111529B2 JPH07111529B2 (en) | 1995-11-29 |
Family
ID=17098122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24305488A Expired - Lifetime JPH07111529B2 (en) | 1988-09-27 | 1988-09-27 | Organic nonlinear optical material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07111529B2 (en) |
-
1988
- 1988-09-27 JP JP24305488A patent/JPH07111529B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07111529B2 (en) | 1995-11-29 |
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