JPH058715B2 - - Google Patents
Info
- Publication number
- JPH058715B2 JPH058715B2 JP60044801A JP4480185A JPH058715B2 JP H058715 B2 JPH058715 B2 JP H058715B2 JP 60044801 A JP60044801 A JP 60044801A JP 4480185 A JP4480185 A JP 4480185A JP H058715 B2 JPH058715 B2 JP H058715B2
- Authority
- JP
- Japan
- Prior art keywords
- anthryl
- dimethylgermane
- compound
- novel
- general formula
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 14
- -1 di(9-anthryl)dimethylgermane compound Chemical class 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- QGMXETIFYMAMGW-UHFFFAOYSA-N di(anthracen-9-yl)-dimethylgermane Chemical compound C1=CC=C2C([Ge](C)(C=3C4=CC=CC=C4C=C4C=CC=CC4=3)C)=C(C=CC=C3)C3=CC2=C1 QGMXETIFYMAMGW-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- OXTURSYJKMYFLT-UHFFFAOYSA-N dichlorogermane Chemical compound Cl[GeH2]Cl OXTURSYJKMYFLT-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004896 high resolution mass spectrometry Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- YRMRYBWOAURIMP-UHFFFAOYSA-N 9-(anthracen-9-ylmethyl)anthracene Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C4C=CC=CC4=3)=C(C=CC=C3)C3=CC2=C1 YRMRYBWOAURIMP-UHFFFAOYSA-N 0.000 description 3
- RUIGDFHKELAHJL-UHFFFAOYSA-N dimethylgermane Chemical class C[GeH2]C RUIGDFHKELAHJL-UHFFFAOYSA-N 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- YQECBLVSMFAWIZ-UHFFFAOYSA-N dichloro(dimethyl)germane Chemical compound C[Ge](C)(Cl)Cl YQECBLVSMFAWIZ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- XMWJLKOCNKJERQ-UHFFFAOYSA-N 1-bromoanthracene Chemical compound C1=CC=C2C=C3C(Br)=CC=CC3=CC2=C1 XMWJLKOCNKJERQ-UHFFFAOYSA-N 0.000 description 1
- ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 9-bromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=CC2=C1 ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 229910000078 germane Inorganic materials 0.000 description 1
- 150000002290 germanium Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C=CC3=CC2=C1 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Landscapes
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Description
【発明の詳細な説明】
〔発明の利用分野〕
本発明は、新規ジ（９−アントリル）ジメチル
ゲルマン系化合物のおよびその製造方法に関す
る。DETAILED DESCRIPTION OF THE INVENTION [Field of Application of the Invention] The present invention relates to a novel di(9-anthryl)dimethylgermane compound and a method for producing the same.
フオトクロミツク材料は、光によつて可逆的に
その色調が変化することから、光記録材料として
の応用が期待され、広く研究されている。例え
ば、無機化合物としてはCaF2およびNaFなどの
結晶が、また有機化合物としてはスピロピランお
よびその誘導体がそれぞれ主に研究されている。
有機材料は、無機材料にくらべて安定な薄膜を容
易に作製できる点ですぐれている。
Photochromic materials are widely studied because their color tone changes reversibly with light, and are expected to be used as optical recording materials. For example, crystals such as CaF 2 and NaF are mainly studied as inorganic compounds, and spiropyran and its derivatives are mainly studied as organic compounds.
Organic materials are superior to inorganic materials in that stable thin films can be easily produced.
（発明、第82巻、1985年、第１号、頁50〜55）
〔発明の目的〕
本発明の目的は、可逆的に光学特性を変化させ
ることのできる新規なジ（９−アントリル）ジメ
チルゲルマン系化合物のおよびその製造方法を提
供することにある。(Invention, Vol. 82, 1985, No. 1, pp. 50-55) [Object of the Invention] The object of the present invention is to develop a novel di(9-anthryl) dimethyl compound whose optical properties can be reversibly changed. An object of the present invention is to provide a germane compound and a method for producing the same.
従来、ジ（９−アントリル）メタンは光照射に
よつて、〔４＋４〕付加体を与えることが知られ
ていた。このジ（９−アントリル）メタンのゲル
マニウム類縁体を合成し、その光反応性を調べた
結果、以下に示す、新規なジ（９−アントリル）
ジメチルゲルマン系化合物の光学特性が、可逆的
に変化することを見出した。
It has been known that di(9-anthryl)methane gives a [4+4] adduct when irradiated with light. As a result of synthesizing a germanium analog of this di(9-anthryl)methane and examining its photoreactivity, we found that the following novel di(9-anthryl)methane
We have discovered that the optical properties of dimethylgermane compounds change reversibly.
本発明の新規ジ（９−アントリル）ジメチルゲ
ルマン系化合物は、以下の一般式(1)で示される。 The novel di(9-anthryl)dimethylgermane compound of the present invention is represented by the following general formula (1).
ただし、一般式(1)中のＲは、水素またはアルキ
ル基を表す。 However, R in general formula (1) represents hydrogen or an alkyl group.
本発明による、新規ジ（９−アントリル）ジメ
チルゲルマン系化合物は、たとえば次のような反
応により合成できる。 The novel di(9-anthryl)dimethylgermane compound according to the present invention can be synthesized, for example, by the following reaction.
ジ（９−アントリル）ジメチルゲルマン（一般
式(1)において、Ｒ＝水素である化合物）は、９−
ブロモアントラセンをｔ−ブチルリチウムでリチ
オ化したのち、ジクロロジメチルゲルマンと反応
させることにより合成できる。 Di(9-anthryl)dimethylgermane (a compound in which R=hydrogen in general formula (1)) is 9-
It can be synthesized by lithiation of bromoanthracene with t-butyllithium and then reacting with dichlorodimethylgermane.
以下、本発明の合成例および実施例を示す。 Synthesis examples and examples of the present invention are shown below.
合成例
アルゴン雰囲気下、−70℃の９−ブロモアント
ラセン（2.50ｇ）のテトラヒドロフラン溶液
（100ml）にｔ−ブチルリチウムのペンタン溶液
（1.74mol／）を滴下した。−70℃まで冷した溶
液中にジクロロジメチルゲルマン（845mg）の５
mlテトラヒドロフラン溶液を滴下した。Synthesis Example Under an argon atmosphere, a solution of t-butyllithium in pentane (1.74 mol/) was added dropwise to a tetrahydrofuran solution (100 ml) of 9-bromoanthracene (2.50 g) at -70°C. of dichlorodimethylgermane (845 mg) in a solution cooled to -70°C.
ml tetrahydrofuran solution was added dropwise.
−70℃で30分間攪拌後、１時間かけて室温にも
どした。溶媒を留去し、得られた残渣をベンゼン
に溶かし、塩をろ別後、シリカゲルカラムに通し
て分解物を除いた。ベンゼンとエタノールの混合
溶媒から再結晶することにより、本発明のジ（９
−アントリル）ジメチルゲルマン（淡黄色）を得
た。同定は水素核磁気共鳴スペクトル（ Ｈ−
NMR）および高分解能質量分析スペクトルによ
つた。 After stirring at -70°C for 30 minutes, the mixture was returned to room temperature over 1 hour. The solvent was distilled off, the resulting residue was dissolved in benzene, the salt was filtered off, and the residue was passed through a silica gel column to remove decomposed products. The di(9) of the present invention was recrystallized from a mixed solvent of benzene and ethanol.
-anthryl)dimethylgermane (light yellow) was obtained. Identification was made using hydrogen nuclear magnetic resonance spectroscopy (H-
NMR) and high-resolution mass spectrometry spectra.
その結果を次に示す。 The results are shown below.
収率＝68％
融点＝166〜167℃
水素核磁気共鳴 （δppm／CCl4）
1.39 （6H、シングレツト）
7.0〜7.5 （8H、マルチプレツト）
7.8〜8.0 （4H、マルチプレツト）
8.2〜8.4 （6H、マルチプレツト）
高分解能質量分析
C30H24 74Geの計算値＝458.1090
実測値＝458.1123
実施例
上記の合成例で合成した本発明新規化合物ジ
（９−アントリル）ジメチルゲルマン（淡黄色）
（0.11mmol）のベンゼン溶液（７ml）を内径８mm
のパイレツクス管に入れ、脱気した後、高圧水銀
灯（459W）を用いて１時間光照射した。反応物
を薄層クロマトグラフ（シリカゲル）で精製し、
13，13−ジメチル−5a，13b−ジヒドロ−５，
13a−オルト−ベンゼノ−13H−13−ゲルマシク
ロペンタ〔rst〕ペンタフエン（無色）を得た。
同定は水素核磁気共鳴および高分解能質量分析に
よつた。その結果を以下に示す。 Yield = 68% Melting point = 166-167℃ Hydrogen nuclear magnetic resonance (δppm/CCl 4 ) 1.39 (6H, singlet) 7.0-7.5 (8H, multiplet) 7.8-8.0 (4H, multiplet) 8.2-8.4 (6H , multiplet) High-resolution mass spectrometry Calculated value of C 30 H 24 74 Ge = 458.1090 Actual value = 458.1123 Example New compound of the present invention di(9-anthryl)dimethylgermane synthesized in the above synthesis example (light yellow)
(0.11 mmol) benzene solution (7 ml) with an inner diameter of 8 mm
The sample was placed in a Pyrex tube, degassed, and then irradiated with light using a high-pressure mercury lamp (459W) for 1 hour. The reaction product is purified by thin layer chromatography (silica gel),
13,13-dimethyl-5a,13b-dihydro-5,
13a-ortho-benzeno-13H-13-germacyclopenta[rst]pentaphene (colorless) was obtained.
Identification was based on hydrogen nuclear magnetic resonance and high-resolution mass spectrometry. The results are shown below.
収率＝71％
融点＝194℃（分解）
水素核磁気共鳴 （δppm／CCl4）
0.95 （3H、シングレツト）
1.43 （3H、シングレツト）
3.26（1H、ダブレツト、スピン−スピン分裂＝
12.0，3.2，2.4，1.8Hz）
3.90（1H、ダブレツト、スピン−スピン分裂＝
12.0）
4.25（1H、ダブレツト、スピン−スピン分裂＝
2.4Hz）
5.75（1H、２つのダブレツト、スピン−スピン
分裂＝9.6，3.2Hz）
6.14（1H、２つのダブレツト、スピン−スピン
分裂＝9.6，1.8Hz）
6.6〜7.8（13H、マルチプレツト）
高分解能質量分析
C30H24 74Geの計算値＝458.1090
実測値＝458.1103
実施例 ２
実施例１で合成した13，13−ジメチル−5a，
13b−ジヒドロ−５，13a− ｏ −ベンゼノ−
13H−13−ゲルマシクロペンタ〔rst〕ペンタフ
エン（無色）80mgのベンゼン溶液（１ml）を封管
中200℃で１時間加熱したところ定量的にジ（９
−アントリル）ジメチルゲルマン（淡黄色）を再
生した。 Yield = 71% Melting point = 194℃ (decomposition) Hydrogen nuclear magnetic resonance (δppm/CCl 4 ) 0.95 (3H, singlet) 1.43 (3H, singlet) 3.26 (1H, doublet, spin-spin splitting =
12.0, 3.2, 2.4, 1.8Hz) 3.90 (1H, doublet, spin-spin splitting =
12.0) 4.25 (1H, doublet, spin-spin splitting =
2.4Hz) 5.75 (1H, 2 doublets, spin-spin splitting = 9.6, 3.2Hz) 6.14 (1H, 2 doublets, spin-spin splitting = 9.6, 1.8Hz) 6.6-7.8 (13H, multiplet) High resolution Mass spectrometry C 30 H 24 74 Ge calculated value = 458.1090 Actual value = 458.1103 Example 2 13,13-dimethyl-5a synthesized in Example 1,
13b-dihydro-5,13a- o -benzeno-
When a benzene solution (1 ml) containing 80 mg of 13H-13-germacyclopenta[rst]pentaphene (colorless) was heated in a sealed tube at 200℃ for 1 hour, di(9)
-anthryl)dimethylgermane (light yellow) was regenerated.
［発明の効果］
以上述べたように、本発明の新規ジ（９−アン
トリル）ジメチルゲルマン系化合物は、光照射に
より色調および構造の異なる〔４＋２〕付加体を
高収率で生成し、その〔４＋２〕付加体は加熱に
より定量的に原料を再生する。したがつてこの色
調の可逆的変化を利用して、本新規化合物を書き
換え可能型光デイスクの記録媒体に適用できる。
たとえば上記合成例の方法で合成した化合物を、
ベンゼンに溶解して得たベンゼン溶液（５〜10重
量％）を基板上に塗布し、乾燥成膜する。これに
レーザー光等を照射すると局部的な色調が変化
し、照射部分と他の部分との光線の反射率の差が
生じる。この反射率の差の生成と検出により、情
報の記録と再生が可能である。次に、色調の変化
した部分をレーザー光等で加熱すれば色調はもと
に戻り、記録した情報の消去ができる。[Effects of the Invention] As described above, the novel di(9-anthryl)dimethylgermane compound of the present invention produces [4+2] adducts with different colors and structures in high yield when irradiated with light, and 4+2] The adduct regenerates the raw material quantitatively by heating. Therefore, by utilizing this reversible change in color tone, the present novel compound can be applied to recording media for rewritable optical discs.
For example, the compound synthesized by the method of the above synthesis example,
A benzene solution (5 to 10% by weight) obtained by dissolving in benzene is applied onto a substrate and dried to form a film. When this is irradiated with laser light or the like, the local color tone changes, and a difference in light reflectance occurs between the irradiated area and other areas. By generating and detecting this reflectance difference, information can be recorded and reproduced. Next, by heating the area where the color tone has changed with a laser beam or the like, the color tone will return to its original state and the recorded information can be erased.
また、本新規化合物は光照射による色調変化と
同時に構造も変化するので、溶媒への溶解度が光
照射前後で変化する。これを利用して本新規化合
物を光レジストに用いることができる。たとえば
上記と同様の方法により作成した本新規化合物薄
膜上にマスクをのせ光照射すると、マスクされた
部分とされていない部分とで溶媒への溶解度の差
が生じる。この薄膜を溶媒で処理することにより
レジストパターンを形成できる。 Furthermore, since the structure of this new compound changes at the same time as the color tone changes due to light irradiation, the solubility in a solvent changes before and after light irradiation. Taking advantage of this, the new compound can be used in photoresists. For example, when a mask is placed on a thin film of the novel compound prepared by a method similar to that described above and irradiated with light, a difference in solubility in the solvent occurs between the masked portion and the unmasked portion. A resist pattern can be formed by treating this thin film with a solvent.
Claims (1)
素を示す。）で表される化合物よりなることを特
徴とする新規ジ（９−アントリル）ジメチルゲル
マン系化合物。 ２ ジ（９−アントリル）ジメチルゲルマンであ
ることを特徴とする特許請求の範囲第１項記載の
新規ジ（９−アントリル）ジメチルゲルマン系化
合物。 ３ 一般式(2)で表される化合物と、ジクロロゲル
マン(3)とを反応させて、一般式(1)で示される化合
物を得ることを特徴とする新規ジ（９−アントリ
ル）ジメチルゲルマン系化合物の製造方法。 ただし一般式(1)と(2)の中のＲはたとえば水素な
どの置換基である。 ４ 一般式(2)で表される化合物が、 であり、一般式(1)で示される化合物が であることを特徴とする特許請求の範囲第３項記
載の新規ジ（９−アントリル）ジメチルゲルマン
系化合物の製造方法。[Claims] 1 General formula (1) (However, R in general formula (1) represents an alkyl group or hydrogen.) A novel di(9-anthryl)dimethylgermane compound characterized by comprising a compound represented by the following. 2. The novel di(9-anthryl)dimethylgermane compound according to claim 1, which is di(9-anthryl)dimethylgermane. 3. A novel di(9-anthryl)dimethylgermane system characterized in that a compound represented by general formula (2) and dichlorogermane (3) are reacted to obtain a compound represented by general formula (1). Method of manufacturing the compound. However, R in general formulas (1) and (2) is a substituent such as hydrogen. 4 The compound represented by general formula (2) is , and the compound represented by general formula (1) is A method for producing a novel di(9-anthryl)dimethylgermane compound according to claim 3, which is characterized in that:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60044801A JPS61205290A (en) | 1985-03-08 | 1985-03-08 | Novel di(9-anthryl)dimethylgermane compound and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60044801A JPS61205290A (en) | 1985-03-08 | 1985-03-08 | Novel di(9-anthryl)dimethylgermane compound and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61205290A JPS61205290A (en) | 1986-09-11 |
| JPH058715B2 true JPH058715B2 (en) | 1993-02-02 |
Family
ID=12701526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60044801A Granted JPS61205290A (en) | 1985-03-08 | 1985-03-08 | Novel di(9-anthryl)dimethylgermane compound and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61205290A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4708727B2 (en) * | 2004-04-27 | 2011-06-22 | 富士フイルム株式会社 | Organic electroluminescence device |
| DE112020005305T5 (en) | 2019-12-17 | 2022-09-15 | Murata Manufacturing Co., Ltd. | ELECTRONIC SWITCH |
-
1985
- 1985-03-08 JP JP60044801A patent/JPS61205290A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61205290A (en) | 1986-09-11 |
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