JPH0372594A - Chemiluminescent material - Google Patents
Chemiluminescent materialInfo
- Publication number
- JPH0372594A JPH0372594A JP20912189A JP20912189A JPH0372594A JP H0372594 A JPH0372594 A JP H0372594A JP 20912189 A JP20912189 A JP 20912189A JP 20912189 A JP20912189 A JP 20912189A JP H0372594 A JPH0372594 A JP H0372594A
- Authority
- JP
- Japan
- Prior art keywords
- dibromoanthracene
- peroxide
- phenylbenzoyl
- luminescence
- intensity
- 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.)
- Pending
Links
- 239000000463 material Substances 0.000 title abstract description 9
- BRUOAURMAFDGLP-UHFFFAOYSA-N 9,10-dibromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=C(Br)C2=C1 BRUOAURMAFDGLP-UHFFFAOYSA-N 0.000 claims abstract description 8
- RNLJIWZJKTVLRQ-UHFFFAOYSA-N phenyl benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC1=CC=CC=C1 RNLJIWZJKTVLRQ-UHFFFAOYSA-N 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 230000005281 excited state Effects 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000004020 luminiscence type Methods 0.000 abstract description 14
- 238000000354 decomposition reaction Methods 0.000 abstract description 2
- 230000005284 excitation Effects 0.000 abstract 1
- 238000001228 spectrum Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000005979 thermal decomposition reaction Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- MAOWXLISNQNMLK-UHFFFAOYSA-N 1,2-dibromoanthracene Chemical compound C1=CC=CC2=CC3=C(Br)C(Br)=CC=C3C=C21 MAOWXLISNQNMLK-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000254158 Lampyridae Species 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- HWYHZTIRURJOHG-UHFFFAOYSA-N luminol Chemical compound O=C1NNC(=O)C2=C1C(N)=CC=C2 HWYHZTIRURJOHG-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
Landscapes
- Luminescent Compositions (AREA)
Abstract
Description
【発明の詳細な説明】
Ａ、産業上の利用分野
本発明は、有機物の相互作用による新しい化学発光メカ
ニズムを有する化学発光材料に関するもＢ９発明の概要
本発明は、有機物を用いた化学発光材料において、
芳香族炭化水素である９、１０−ジブロモアントラセン
とフェニルベンゾイルペルオキサイドとを反応させて電
荷移動錯体を作製することによって、
肉眼で確認できる強さの発光を得られるようにしたもの
である。Detailed Description of the Invention A. Field of Industrial Application The present invention relates to chemiluminescent materials having a new chemiluminescent mechanism due to the interaction of organic substances. B9 Summary of the Invention The present invention relates to chemiluminescent materials using organic substances. By reacting 9,10-dibromoanthracene, an aromatic hydrocarbon, and phenylbenzoyl peroxide to create a charge transfer complex, it is possible to obtain luminescence with an intensity that can be seen with the naked eye.
Ｃ０従来の技術及び発明が解決しようとする課題従来ホ
タルの発光、ルミノール発光など酵素の関与したと考え
られる発光ならびに発光材料は多く見い出されている。C0 Prior Art and Problems to be Solved by the Invention Conventionally, many luminescent materials and luminescent materials thought to be related to enzymes, such as firefly luminescence and luminol luminescence, have been discovered.
しかし、それ以外の化学発光の例は非常に少ない。例え
ば芳香族炭化水素である９、１０−ジブロモアントラセ
ンは、ケイ光を発する材料として知られているが、肉眼
で確認できる強さのケイ光あるいは化学発光を示したと
いう報告はまだない。However, there are very few other examples of chemiluminescence. For example, 9,10-dibromoanthracene, which is an aromatic hydrocarbon, is known as a material that emits fluorescence, but there has been no report yet that it exhibits fluorescence or chemiluminescence with an intensity that can be seen with the naked eye.
本発明は、従来の化学発光とは全く異なる、有機物の相
互作用による新しい化学発光メカニズムを有する化学発
光材料を提供することを目的とする。An object of the present invention is to provide a chemiluminescent material having a new chemiluminescent mechanism based on the interaction of organic substances, which is completely different from conventional chemiluminescence.
９１課題を解決するための手段及び作用芳香族炭化水素
である９、１０−ジブロモアントラセンとフェニルベン
ゾイルペルオキサイド（過酸化ビス〈２−フェニル〉）
とを反応させると、９゜１０−ジブロモアントラセンが
基底状態で電荷移動錯体を生成し、本発明はこの電荷移
動錯体より成るものである。なおフェニルベンゾイルペ
ルオキサイドは以下略してｒ２−ｐｈＢＰｏコと称する
。９，１０−ジブロモアントラセンと２−ｐｈＢＰＯの
構造式は次のとおりである。91 Means and effects for solving the problems 9,10-dibromoanthracene, which is an aromatic hydrocarbon, and phenylbenzoyl peroxide (bis<2-phenyl peroxide>)
When reacted with 9°10-dibromoanthracene, a charge transfer complex is formed in the ground state, and the present invention consists of this charge transfer complex. Note that phenylbenzoyl peroxide is hereinafter abbreviated as r2-phBPo. The structural formulas of 9,10-dibromoanthracene and 2-phBPO are as follows.
（以下余白）
（９゜
０
ジブロモアントラセンの構造式）
上記の電荷移動錯体は、９．１０−ジブロモアントラセ
ン及び２−ｐｈＢＰＯを夫々Ｘ、Ｙとす−す
ると、（Ｘ’ ・・・Ｙ’）で表される物質であり、
これを酸素雰囲気中で２−ｐｈｎｐｏが分解する温度以
上に加熱すると、２−ｐｈＢＰｏの分解により生成され
た３ 、 ４−Ｂｅｎｚｏｃｕｍａｒｉｎが酸素と作用
して、３ 、４−Ｂｅｎｚｏｃｕｍａｒｉｎは基底状態
へ落ちる。このとき９．１０−ジブロモアントラセンは
酸素から電子を受は取って励起状態となり、青白く発光
する。この発光は、酸素が存在しない場合には、９．１
０−ジブロモアントラセンへの電子の受は渡しの方法が
ないため起こらない。(Blank below) (9゜0 Structural formula of dibromoanthracene) The above charge transfer complex has the structure (X'...Y') where 9.10-dibromoanthracene and 2-phBPO are respectively X and Y. It is a substance expressed by
When this is heated above the temperature at which 2-phnpo decomposes in an oxygen atmosphere, 3,4-Benzocumarin produced by the decomposition of 2-phBPo interacts with oxygen, and 3,4-Benzocumarin falls to the ground state. At this time, 9.10-dibromoanthracene receives and takes electrons from oxygen, becomes excited, and emits blue-white light. This luminescence, in the absence of oxygen, is 9.1
Electron acceptance to 0-dibromoanthracene does not occur because there is no transfer method.
Ｅ、実施例
９．１０−ジブロモアントラセンｌＯｊ＋９をアセトニ
トリル（ＣＨｓ ＣＮ ） １０ ｍＱに室温で溶かし
、更に２−ｐｈＢｐｏを１０ｍｇ加えて溶解する。これ
により９．ＩＯ−ジブロモアントラセンと２−ｐｈＢＰ
ｏの大部分は電荷移動錯体を形成する。E, Example 9.10-Dibromoanthracene lOj+9 is dissolved in 10 mQ of acetonitrile (CHsCN) at room temperature, and further 10 mg of 2-phBpo is added and dissolved. As a result, 9. IO-dibromoanthracene and 2-phBP
The majority of o forms charge transfer complexes.
次にこの溶解物を空気中にて温度７８℃に加熱すると、
約４０分間化学発光スペクトルをＩ！！測した。Next, when this melt is heated in air to a temperature of 78°C,
I! chemiluminescence spectrum for about 40 minutes! ! I measured it.
第１図の（１）、（２）は、夫々この化学発光スペクト
ルと９．１０−ジブロモアントラセンのケイ光スペクト
ルとを示し、この図かられかるように２つのスペクトル
は一致しており、発光種は９゜ｌＯ−ジブロモアントラ
センであると考えられる。Figure 1 (1) and (2) show this chemiluminescence spectrum and the fluorescence spectrum of 9.10-dibromoanthracene, respectively.As can be seen from this figure, the two spectra coincide, and the luminescence The species is believed to be 9°lO-dibromoanthracene.
なお、この発光は白青色であり、目視で十分観測できる
明るさを持っていた。This emission was white-blue and bright enough to be visually observed.
次に９．ｌＯ−ジブロモアントラセンの溶解量を１０ｍ
ｇ〜９０ｍｇまで変化させ（他の条件は上述実施例と同
じ）、発光強度と９．ｌＯ−ジブロモアントラセンの濃
度との関係を調べたところ、第２図に示す結果が得られ
た。この結果かられかるように、９．１０−ジブロモア
ントラセンの濃度に比例して発光強度が増大し、９．ｌ
Ｏ−ジブロモアントラセンの量は発光強度に重要な寄与
をしている。Next 9. The dissolved amount of lO-dibromoanthracene is 10 m
g to 90 mg (other conditions are the same as in the above example), and the luminescence intensity and 9. When the relationship with the concentration of lO-dibromoanthracene was investigated, the results shown in FIG. 2 were obtained. As can be seen from this result, the luminescence intensity increases in proportion to the concentration of 9.10-dibromoanthracene. l
The amount of O-dibromoanthracene makes an important contribution to the emission intensity.
また発光強度と反応温度との関係を調べたところ、第３
図に示すデータが得られた。第３図中（１）〜（３）は
夫々温度７８℃、４０℃及び１５０℃にて反応させた場
合のデータである。この結果かられかるように、温度４
０℃では２−ｐｈＢＰＯの熱分解速度が遅いので長時間
の発光となり、温度が高くなるにつれて発光強度が増大
する。温度１５０℃では２−ｐｈＢＰｏの熱分解速度が
大きいため短時間の発光となる。Furthermore, when we investigated the relationship between luminescence intensity and reaction temperature, we found that the third
The data shown in the figure were obtained. In FIG. 3, (1) to (3) are data obtained when reactions were performed at temperatures of 78°C, 40°C, and 150°C, respectively. As can be seen from this result, the temperature 4
At 0°C, the rate of thermal decomposition of 2-phBPO is slow, so light is emitted for a long time, and the intensity of the emitted light increases as the temperature rises. At a temperature of 150° C., the thermal decomposition rate of 2-phBPo is high, resulting in light emission for a short time.
Ｆ０発明の効果
本発明によれば、簡単に合成できる有機過酸化物（２−
ｐｈＢＰＯ）を用い、熱分解といった簡単な手法により
十分目視できる発光を得ることができ、従って例えば熱
エネルギーを光エネルギーに変える素子として有効に利
用できる可能性がある。また空気中で常温（例えば４０
℃以上）で発光を目視できることから、感温センサーと
して応用できる。更に発光強度を９．１０−ジブロモア
ントラセンあるいは２−ｐｈＢＰＯの量を変えることで
コントロールできると共に、その継続時間を反応温度で
コントロールできるから、化学発光を任意に調整できる
。Effect of the F0 Invention According to the present invention, organic peroxide (2-
phBPO), it is possible to obtain sufficiently visible light emission by a simple method such as thermal decomposition, and therefore, there is a possibility that it can be effectively used, for example, as an element that converts thermal energy into light energy. Also, in the air at room temperature (for example, 40
Since the luminescence can be visually observed at temperatures above ℃), it can be used as a temperature sensor. Furthermore, the luminescence intensity can be controlled by changing the amount of 9.10-dibromoanthracene or 2-phBPO, and the duration can be controlled by the reaction temperature, so chemiluminescence can be adjusted as desired.
第１図は発光スペクトルを示すスペクトル観測図、第２
図は９．１０−ジブロモアントラセンの濃度と発光強度
との関係を示すグラフ、第３図は発光強度と反応温度と
の関係を示すグラフである。Figure 1 is a spectrum observation diagram showing the emission spectrum, Figure 2 is a spectrum observation diagram showing the emission spectrum.
The figure is a graph showing the relationship between the concentration of 9.10-dibromoanthracene and the luminescence intensity, and FIG. 3 is a graph showing the relationship between the luminescence intensity and reaction temperature.
Claims (1)
ゾイルペルオキサイドとを反応させて得た電荷移動錯体
より成り、この電荷移動錯体を酸素雰囲気中でフェニル
ベンゾイルペルオキサイドが分解する温度以上に加熱す
ることにより、９，１０−ジブロモアントラセンが励起
状態となって発光することを特徴とする化学発光材料。(1) Consists of a charge transfer complex obtained by reacting 9,10-dibromoanthracene and phenylbenzoyl peroxide, and by heating this charge transfer complex in an oxygen atmosphere to a temperature higher than the temperature at which phenylbenzoyl peroxide decomposes. , 9,10-dibromoanthracene is in an excited state and emits light.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20912189A JPH0372594A (en) | 1989-08-11 | 1989-08-11 | Chemiluminescent material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20912189A JPH0372594A (en) | 1989-08-11 | 1989-08-11 | Chemiluminescent material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0372594A true JPH0372594A (en) | 1991-03-27 |
Family
ID=16567636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20912189A Pending JPH0372594A (en) | 1989-08-11 | 1989-08-11 | Chemiluminescent material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0372594A (en) |
-
1989
- 1989-08-11 JP JP20912189A patent/JPH0372594A/en active Pending
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