JP3080246B2 - Organic single crystal - Google Patents
Organic single crystalInfo
- Publication number
- JP3080246B2 JP3080246B2 JP03181422A JP18142291A JP3080246B2 JP 3080246 B2 JP3080246 B2 JP 3080246B2 JP 03181422 A JP03181422 A JP 03181422A JP 18142291 A JP18142291 A JP 18142291A JP 3080246 B2 JP3080246 B2 JP 3080246B2
- Authority
- JP
- Japan
- Prior art keywords
- single crystal
- benzothiadiazole
- nitro
- organic
- organic single
- 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 - Fee Related
Links
- 239000013078 crystal Substances 0.000 title claims description 43
- IWQKAMJGVIHECB-UHFFFAOYSA-N 4-nitro-2,1,3-benzothiadiazole Chemical compound [O-][N+](=O)C1=CC=CC2=NSN=C12 IWQKAMJGVIHECB-UHFFFAOYSA-N 0.000 claims description 15
- 230000003287 optical effect Effects 0.000 description 27
- 238000000034 method Methods 0.000 description 21
- 239000000463 material Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000011521 glass Substances 0.000 description 4
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 3
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 3
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000005693 optoelectronics Effects 0.000 description 3
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 238000000935 solvent evaporation Methods 0.000 description 2
- 238000012916 structural analysis Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 238000005092 sublimation method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000002109 crystal growth method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000015220 hamburgers Nutrition 0.000 description 1
- GQYHUHYESMUTHG-UHFFFAOYSA-N lithium niobate Chemical compound [Li+].[O-][Nb](=O)=O GQYHUHYESMUTHG-UHFFFAOYSA-N 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000009022 nonlinear effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
Description
【０００１】[0001]
【産業上の利用分野】４−ニトロ−２,１,３−ベンゾチ
アジアゾール分子より構成された単斜晶系空間群Ｐｎに
属する有機単結晶に関するものであり、これは非線形光
学、電気光学に適応するものである。またこれらの効果
を利用しうるすべてのオプトエレクトロニクス装置に応
用することができる。The present invention relates to an organic single crystal belonging to a monoclinic space group Pn composed of 4-nitro-2,1,3-benzothiadiazole molecules, which is applicable to nonlinear optics and electro-optics. Is what you do. Further, the present invention can be applied to all optoelectronic devices that can utilize these effects.
【０００２】[0002]
【従来の技術】非線形光学効果とは、レーザーのような
強い電場をもった光をあてたとき光の強い電場により物
質が分極し、この分極による光高調波の発生や入射した
光自身が変化する現象をいう。この現象の主なものとし
て光高調波発生、光混合、誘導散乱、多光子吸収などが
あげられる。特に二次の非線形光学効果の中の光第二高
調波発生（ＳＨＧ）は注目するべきところがあり、波長
変換素子などのオプトエレクトロニクスの基盤技術に応
用できる。これまでリン酸２水素カリウム、ニオブ酸リ
チウムなどの無機材料が二次の非線形光学効果を示すも
のとして中心に研究が進められてきた。2. Description of the Related Art A nonlinear optical effect is a phenomenon in which when a light having a strong electric field such as a laser is applied, a substance is polarized by the strong electric field of the light, thereby generating optical harmonics due to the polarization and changing the incident light itself. The phenomenon that does. Main phenomena of this phenomenon include optical harmonic generation, optical mixing, stimulated scattering, and multiphoton absorption. In particular, optical second harmonic generation (SHG) in the second-order nonlinear optical effect is noteworthy, and can be applied to basic technologies of optoelectronics such as wavelength conversion elements. Until now, research has been focused on inorganic materials such as potassium dihydrogen phosphate and lithium niobate exhibiting a second-order nonlinear optical effect.
【０００３】最近、２−メチル−４−ニトロアニリン
（ＭＮＡ）などの有機材料が、従来の無機材料を遥かに
上回る二次の非線形光学効果を示すことがわかり非線形
光学材料として注目されている（特開昭５５−５００９
６０号公報）。有機非線形材料を波長変換素子として使
用するには、単結晶の形にすることが一つの方法であ
る。有機非線形光学材料の二次の非線形光学効果発生の
ためには、ベンゼンのような非極在電子をもった有機分
子の両端に電子供給基と電子受容基を配置することによ
り、有機分子内の非極在電子の移動を非対称にし、さら
に、その単結晶状態での分子配置も非中心対称構造とす
ることが不可欠である。Recently, it has been found that organic materials such as 2-methyl-4-nitroaniline (MNA) exhibit a second-order nonlinear optical effect far exceeding conventional inorganic materials, and are attracting attention as nonlinear optical materials ( JP-A-55-5009
No. 60). One way to use an organic nonlinear material as a wavelength conversion element is to make it a single crystal. In order to generate the second-order nonlinear optical effect of organic nonlinear optical materials, an electron supply group and an electron accepting group are arranged at both ends of an organic molecule having non-polar electrons such as benzene, so that the It is essential that the transfer of nonpolar electrons be asymmetric and that the molecular arrangement in a single crystal state be a noncentrosymmetric structure.
【０００４】波長変換素子として有機単結晶を使う場合
には、その有機単結晶のカットオフ波長、大きさ、加工
性などが重要な要素になる。有機単結晶が入射基本波お
よび第二高調波の波長領域に電子遷移吸収を持つと、そ
の熱振動により結晶が破壊されたり、第二高調波が発生
しないなどの原因となる。従って、有機単結晶のカット
オフ波長を充分に短くする必要がある。第二高調波の強
度は、結晶の光路作用長の２乗に比例するので、有機単
結晶は大きければ大きいほど好ましい。一般に、有機単
結晶は、無機単結晶と比較して機械的強度に劣り、研磨
加工が困難であると言われている。すなわち、高強度で
加工性の優れた有機単結晶が要求される。When an organic single crystal is used as a wavelength conversion element, the cutoff wavelength, size, workability, and the like of the organic single crystal are important factors. When the organic single crystal has an electron transition absorption in the wavelength region of the incident fundamental wave and the second harmonic, the crystal is destroyed by the thermal vibration, and the second harmonic is not generated. Therefore, it is necessary to make the cutoff wavelength of the organic single crystal sufficiently short. Since the intensity of the second harmonic is proportional to the square of the optical path working length of the crystal, the larger the organic single crystal, the more preferable. In general, it is said that an organic single crystal is inferior in mechanical strength to an inorganic single crystal and difficult to be polished. That is, an organic single crystal having high strength and excellent workability is required.
【０００５】単結晶育成法には、昇華法などの化合物が
気相の状態にあるものから析出する方法、溶媒蒸発法な
どの化合物の飽和溶液から析出する方法、チョクラルス
キー法、ブリッジマン−ストックバーガー法などの化合
物の溶融状態から固化させる方法などがあり、有機非線
形化合物の単結晶化にも広く応用されている。[0005] Single crystal growth methods include a method of depositing a compound in a gaseous state, such as a sublimation method, a method of depositing a compound from a saturated solution of a compound, such as a solvent evaporation method, a Czochralski method, and a Bridgman method. There are a method of solidifying a compound from a molten state, such as a stock burger method, and the method is widely applied to single crystallization of an organic nonlinear compound.
【０００６】[0006]
【発明が解決しようとする課題】本発明の目的とすると
ころは、二次の非線形光学効果が大きく、光学材料とし
ての使用波長域を拡大するためにカットオフ波長が短波
長化され、さらには、一定の大きさを持ち加工性のよい
有機単結晶を提供するところにある。An object of the present invention is to provide a large second-order nonlinear optical effect, and to shorten the cutoff wavelength in order to expand the wavelength range used as an optical material. Another object of the present invention is to provide an organic single crystal having a certain size and good workability.
【０００７】[0007]
【課題を解決するための手段】本発明は、式（１）で表
わされる４−ニトロ−２,１,３−ベンゾチアジアゾール
の有機単結晶であるって、特に単斜晶系空間群Ｐｎに属
する有機単結晶である。The present invention relates to an organic single crystal of 4-nitro-2,1,3-benzothiadiazole represented by the formula (1), and particularly to a monoclinic space group Pn. It belongs to an organic single crystal.
【０００８】[0008]
【化１】 Embedded image
【０００９】４−ニトロ−２,１,３−ベンゾチアジアゾ
ールは結晶多形を有し、単結晶を得る条件によって二次
の非線形光学効果をもつものや、二次の非線形光学効果
をもたないものが出来る。そのために二次の非線形光学
効果をもつ有効な結晶を効率よく、簡単に取り出すこと
が重要になる。4-Nitro-2,1,3-benzothiadiazole has a polymorphism and has a second-order nonlinear optical effect or no second-order nonlinear optical effect depending on the conditions for obtaining a single crystal. Things can be done. Therefore, it is important to efficiently and easily extract an effective crystal having a second-order nonlinear optical effect.
【００１０】４−ニトロ−２,１,３−ベンゾチアジアゾ
ールの二次の非線形光学効果をもつ有機単結晶は、種々
条件を定めることにより溶媒蒸発法、昇華法、溶融固化
法などの方法で得ることができ、なかでも溶融固化法の
１つであるブリッジマン−ストックバーガー法は、大型
の結晶を得られ易く、しかも非中心対称性の単斜晶系空
間群Ｐｎに属する二次の非線形光学効果をもつ結晶を得
ることができる。またこのものは非線形光学定数の対角
成分が大きいので光導波路として特に有用である。この
方法によれば、直径３ｍｍ、長さ１０ｍｍ以上の大きさ
の柱状結晶を得ることが出来る。またこのものはカット
オフ波長も４２０ｎｍと短波長域にあり、研磨もしやす
く加工性にも優れている。An organic single crystal having a second-order nonlinear optical effect of 4-nitro-2,1,3-benzothiadiazole can be obtained by a method such as a solvent evaporation method, a sublimation method, and a solidification method by setting various conditions. In particular, the Bridgman-Stockberger method, which is one of the melt-solidification methods, is easy to obtain large crystals, and furthermore, the second-order nonlinear optics belonging to a noncentrosymmetric monoclinic space group Pn. A crystal having an effect can be obtained. This is particularly useful as an optical waveguide because the diagonal component of the nonlinear optical constant is large. According to this method, a columnar crystal having a diameter of 3 mm and a length of 10 mm or more can be obtained. Further, it has a cutoff wavelength of 420 nm in a short wavelength range, and is easily polished and excellent in workability.
【００１１】[0011]
【実施例】以下本発明を実施例に基づいて説明する。DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below based on embodiments.
【００１２】（２,１,３−ベンゾチアジアゾールの合
成）ｏ−フェニレンジアミンと２倍当量の塩化チオニル
をトルエン中で１２時間還流した後、常圧蒸留でやや赤
色に着色した針状結晶を単離した。(Synthesis of 2,1,3-benzothiadiazole) After refluxing o-phenylenediamine and 2 equivalents of thionyl chloride in toluene for 12 hours, a needle-like crystal slightly colored red by atmospheric distillation was converted into a single crystal. Released.
【００１３】（４−ニトロ−２,１,３−ベンゾチアジア
ゾールの合成）２,１,３−ベンゾチアジアゾールと濃硫
酸、濃硝酸を常法によりニトロ化反応させ、４−ニトロ
−２,１,３−ベンゾチアジアゾールを得た。(Synthesis of 4-nitro-2,1,3-benzothiadiazole) Nitration reaction of 2,1,3-benzothiadiazole with concentrated sulfuric acid and concentrated nitric acid is carried out by a conventional method to give 4-nitro-2,1,1. 3-benzothiadiazole was obtained.
【００１４】（４−ニトロ−２,１,３−ベンゾチアジア
ゾールの昇華精製）このようにして得られた４−ニトロ
−２,１,３−ベンゾチアジアゾールをガラス容器に入
れ、真空下で９０℃に加熱して昇華精製した。このもの
の融点は１０９℃であった。(Sublimation purification of 4-nitro-2,1,3-benzothiadiazole) The thus obtained 4-nitro-2,1,3-benzothiadiazole is placed in a glass container and heated at 90 ° C. under vacuum. And purified by sublimation. Its melting point was 109 ° C.
【００１５】（４−ニトロ−２,１,３−ベンゾチアジア
ゾールの単結晶化）４−ニトロ−２,１,３−ベンゾチア
ジアゾールの単結晶はブリッジマン−ストックバーガー
法より得た。図１に結晶育成に用いたブリッジマン−ス
トックバーガー法の装置を示す。ブリッジマン−ストッ
クバーガー法とは、結晶化対象物の有機材料をガラスア
ンプルに詰め、図１の右側のような温度勾配がついたブ
リッジマン−ストックバーガー炉中で融解させ、モータ
ーで点線の矢印の向きにゆっくりと釣り下げて行き、下
部から固化結晶化させる方法である。ブリッジマン−ス
トックバーガー法での単結晶育成には、ガラスアンプル
の引き下げ速度と、ブリッジマン−ストックバーガー炉
内の冷却時のａ〜ｂの温度勾配が重要な条件となり、目
的によって必要な条件を定める。例えば、表１に示す条
件では、単結晶の大きさは（１）の場合直径３ｍｍ、長
さ３５ｍｍ、（２）の場合は直径３ｍｍ、長さ２３ｍｍ
の柱状単結晶がそれぞれ得られた。(Single Crystallization of 4-Nitro-2,1,3-benzothiadiazole) A single crystal of 4-nitro-2,1,3-benzothiadiazole was obtained by the Bridgman-Stockberger method. FIG. 1 shows an apparatus of the Bridgman-Stockberger method used for growing a crystal. In the Bridgman-Stockberger method, an organic material to be crystallized is packed in a glass ampoule, melted in a Bridgman-Stockberger furnace having a temperature gradient as shown in the right side of FIG. This is a method of slowly hanging down in the direction of, and solidifying and crystallizing from the bottom. For growing a single crystal by the Bridgman-Stockberger method, the glass ampoule lowering speed and the temperature gradient a to b during cooling in the Bridgman-Stockberger furnace are important conditions. Determine. For example, under the conditions shown in Table 1, the size of the single crystal is 3 mm in diameter and 35 mm in length in (1), and 3 mm in diameter and 23 mm in length in (2).
Was obtained.
【００１６】[0016]
【表１】 [Table 1]
【００１７】（Ｘ線構造解析の結果）４−ニトロ−２,
１,３−ベンゾチアジアゾールからなる有機単結晶のＸ
線構造解析の結果は図２の通りである。この有機単結晶
は単斜晶系、空間群Ｐｎ、格子定数、ａ＝１４.６８Å,
ｂ＝３.８２Å,ｃ＝１３.７４Å,β＝１１３.９２゜で
あった。単位格子中に４個の４−ニトロ−２,１,３−ベ
ンゾチアジアゾール分子が存在していた。この単結晶は
非中心対称構造を持ち、電子受容性のニトロ基が一方向
に並んでおり、単結晶においての強い二次の非線形光学
効果が期待できる。また劈開面として（００１）,（１
０１）面が現れていた。(Results of X-ray structural analysis) 4-nitro-2,
X of an organic single crystal composed of 1,3-benzothiadiazole
The result of the line structure analysis is as shown in FIG. This organic single crystal is monoclinic, space group Pn, lattice constant, a = 14.68 °,
b = 3.82 °, c = 13.74 °, β = 113.92 °. There were four 4-nitro-2,1,3-benzothiadiazole molecules in the unit cell. This single crystal has a non-centrosymmetric structure, and electron-accepting nitro groups are arranged in one direction, and a strong second-order nonlinear optical effect in the single crystal can be expected. (001), (1)
01) The face was appearing.
【００１８】（密度の測定）浮沈法による密度の測定の
結果１.７ｇ／ｃｍ3であった。また測定中に水との溶解
性は認められなかった。(Measurement of Density) As a result of measuring the density by the floatation method, it was 1.7 g / cm 3 . No solubility with water was observed during the measurement.
【００１９】（カットオフ波長の測定）紫外可視分光光
度計で４−ニトロ−２,１,３−ベンゾチアジアゾールか
らなる有機単結晶のカットオフ波長を測定した結果４２
０ｎｍであった。(Measurement of cut-off wavelength) The result of measuring the cut-off wavelength of an organic single crystal composed of 4-nitro-2,1,3-benzothiadiazole using an ultraviolet-visible spectrophotometer 42
It was 0 nm.
【００２０】（レーザー照射実験の結果）得られた４−
ニトロ−２,１,３−ベンゾチアジアゾールからなる有機
単結晶にＱスイッチ付きＮｄ：ＹＡＧレーザー（１０６
４ｎｍ）を照射したところ第二次高調波の緑の光が観測
された。(Results of laser irradiation experiment)
Nd: YAG laser with Q-switch (106) on organic single crystal composed of nitro-2,1,3-benzothiadiazole
4 nm), green light of the second harmonic was observed.
【００２１】[0021]
【発明の効果】以上の通り本発明に従うと、４−ニトロ
−２,１,３−ベンゾチアジアゾールからなる有機単結晶
は非中心対称構造をもち大きな二次の非線形光学効果が
得られる。また、大きな非線形効果を有する非線形物質
では、一般にカットオフ波長が長波長領域にあり、非線
形光学材料、特に波長変換材料としての使用領域を狭め
ている（ＭＮＡ４８０ｎｍ）が、４−ニトロ−２,１,３
−ベンゾチアジアゾールからなる有機単結晶はカットオ
フ波長が結晶状態で４２０ｎｍであり広波長領域での使
用が可能である。しかもその有機単結晶は他の有機単結
晶と比較して高強度で、水への溶解性がない加工性の富
んだものとなった。本発明による４−ニトロ−２,１,３
−ベンゾチアジアゾールからなる有機単結晶は、従っ
て、波長変換素子、光制御素子などの非線形光学効果及
び電気光学効果を利用した各種の光機能素子材料として
各種の光機能材料として、いろいろな用途が期待でき
る。As described above, according to the present invention, an organic single crystal comprising 4-nitro-2,1,3-benzothiadiazole has a non-centrosymmetric structure and a large second-order nonlinear optical effect can be obtained. Further, in a nonlinear material having a large nonlinear effect, the cutoff wavelength is generally in a long wavelength region, and the use region as a nonlinear optical material, particularly a wavelength conversion material is narrowed (MNA: 480 nm). , 3
The organic single crystal of benzothiadiazole has a cutoff wavelength of 420 nm in a crystalline state, and can be used in a wide wavelength region. Moreover, the organic single crystal has high strength compared to other organic single crystals, and has good processability without solubility in water. 4-nitro-2,1,3 according to the invention
-Organic single crystals composed of benzothiadiazole are expected to have various uses as various optical functional materials as various optical functional element materials utilizing nonlinear optical effects and electro-optical effects such as wavelength conversion elements and optical control elements. it can.
【図１】 ブリッジマン−ストックバーガー法の装置の
図であり、右のグラフはこの装置内の温度と高さの関係
（温度勾配）を表したものである。FIG. 1 is a diagram of an apparatus of the Bridgman-Stockberger method, and the graph on the right shows a relationship between temperature and height (temperature gradient) in the apparatus.
【図２】 ４−ニトロ−２,１,３−ベンゾチアジアゾー
ルからなる有機単結晶のＸ線構造解析の結果である。FIG. 2 shows the result of X-ray structural analysis of an organic single crystal composed of 4-nitro-2,1,3-benzothiadiazole.
１ ガラスアンプル ２ 自動温度調節器 ３ ヒーター ４ 冷却水 ５ 熱煤用シリコンオイル ６ 引き下げ用モーター ７ 炉 ８ 単結晶 ９ 多結晶部 10 溶融部 11 結晶化部 DESCRIPTION OF SYMBOLS 1 Glass ampoule 2 Automatic temperature controller 3 Heater 4 Cooling water 5 Silicon oil for heat soot 6 Motor for pulling down 7 Furnace 8 Single crystal 9 Polycrystal part 10 Melting part 11 Crystallization part
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.7，ＤＢ名) C07D 285/00 - 285/38 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int. Cl. 7 , DB name) C07D 285/00-285/38 CA (STN) REGISTRY (STN)
Claims (1)
ゾール分子からなる単斜晶系空間群Ｐｎに属する有機単
結晶。1. An organic single crystal belonging to a monoclinic space group Pn comprising a 4-nitro-2,1,3-benzothiadiazole molecule.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP03181422A JP3080246B2 (en) | 1991-07-23 | 1991-07-23 | Organic single crystal |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP03181422A JP3080246B2 (en) | 1991-07-23 | 1991-07-23 | Organic single crystal |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0525148A JPH0525148A (en) | 1993-02-02 |
| JP3080246B2 true JP3080246B2 (en) | 2000-08-21 |
Family
ID=16100498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP03181422A Expired - Fee Related JP3080246B2 (en) | 1991-07-23 | 1991-07-23 | Organic single crystal |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3080246B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004296529A (en) * | 2003-03-25 | 2004-10-21 | Mitsubishi Chemicals Corp | Optical amplifier |
-
1991
- 1991-07-23 JP JP03181422A patent/JP3080246B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0525148A (en) | 1993-02-02 |
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