JPH0678300B2 - Novel tetraselenotetracene and its complex - Google Patents

Novel tetraselenotetracene and its complex

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Publication number
JPH0678300B2
JPH0678300B2 JP15844390A JP15844390A JPH0678300B2 JP H0678300 B2 JPH0678300 B2 JP H0678300B2 JP 15844390 A JP15844390 A JP 15844390A JP 15844390 A JP15844390 A JP 15844390A JP H0678300 B2 JPH0678300 B2 JP H0678300B2
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JP
Japan
Prior art keywords
compound
charge transfer
represented
following formula
transfer complex
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
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JP15844390A
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Japanese (ja)
Other versions
JPH0449274A (en
Inventor
文夫 小倉
徹夫 大坪
芳雄 安蘇
久一 宮本
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Osaka Soda Co Ltd
Original Assignee
Daiso Co Ltd
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Description

【発明の詳細な説明】 (産業上の利用分野) 本発明は高導電性の電荷移動錯体及びその成分である電
子供与体に関する。
TECHNICAL FIELD The present invention relates to a highly conductive charge transfer complex and an electron donor as a component thereof.

(従来技術と発明が解決しようとする課題) 有機高導電性物質は銅やアルミニウム等の金属材料に比
べ軽量であり腐蝕性がないこと等から近年特に注目され
つつある。
(Problems to be Solved by Prior Art and Invention) Organic high-conductivity substances have recently been particularly attracting attention because they are lighter in weight than metal materials such as copper and aluminum and have no corrosiveness.

一般に有機物質は電気絶縁性であるが、これに導電性を
付与するには電荷移動錯体を形成させるのがよく、これ
までに種々の電子供与体と電子受容体が合成され、これ
らの組合せから多数の導電性電荷移動錯体が提出されて
いる。
Generally, an organic substance is electrically insulating, but it is better to form a charge transfer complex to impart conductivity to it, and various electron donors and electron acceptors have been synthesized so far. Numerous conductive charge transfer complexes have been proposed.

これらの中で電子供与体成分としてはテトラチアフルバ
レン(TTF),テトラセレノテトラセン(TSeT)等が効
果的な電子供与体としてしばしば利用されている。
Of these, tetrathiafulvalene (TTF) and tetraselenotetracene (TSeT) are often used as effective electron donors as electron donor components.

しかしTSeTはその錯体の導電性の点で未だ充分とは言え
ないだけでなく、溶解性の点でも問題があり、錯体を合
成する際に溶剤の選択,濃度等で一定の制約を受けてい
た。
However, TSeT is not sufficient in terms of the conductivity of the complex, but it also has a problem in solubility, and there were certain restrictions on the selection of solvent, concentration, etc. when synthesizing the complex. .

(課題を解決するための手段) 本発明者らは、上記の点に鑑み、導電性に優れた電荷移
動錯体を与え、しかも優れた溶解性を有する電子供与体
を得る目的で鋭意検討した。その結果、TSeTのセレンの
結合位置を変え、非対称の電子供与体とすることによ
り、TTFより溶解性が改善されるだけでなく、これと他
成分の電子受容体で形成される電荷移動錯体が高導電性
を有することを見出し本発明を完成させるに至ったもの
である。
(Means for Solving the Problem) In view of the above points, the present inventors have made earnest studies for the purpose of providing an electron donor having a charge transfer complex having excellent conductivity and having excellent solubility. As a result, by changing the binding position of selenium of TSeT to make it an asymmetric electron donor, not only the solubility is improved as compared with TTF, but also the charge transfer complex formed by this and the electron acceptor of other components is improved. The inventors have found that they have high conductivity and have completed the present invention.

すなわち本発明は下記式(I)で表わされるナフタセノ
[1,12−cd:4,5−c′d′]ビス[1,2]ジセレノール
及び化合物(I)と他成分の電子受容体で形成された電
荷移動錯体、更に化合物(I)の合成中間体である下記
式(II)で表わされる1,4,5,12−テトラクロロナフタセ
ン,下記式(III)で表わされる1,4,5,5,12,12−ヘキサ
クロロ−5,12−ジヒドロナフタセン及び下記式(IV)で
表わされる2,3−ジヒドロ−5,12−ジヒドロキシ−1,4−
ナフタセンキノンを提供するものである。
That is, the present invention comprises a naphthaceno [1,12-cd: 4,5-c'd '] bis [1,2] diselenol represented by the following formula (I), a compound (I) and an electron acceptor as another component. And a 1,4,5,12-tetrachloronaphthacene represented by the following formula (II) which is a synthetic intermediate of the compound (I), 1,4, represented by the following formula (III): 5,5,12,12-hexachloro-5,12-dihydronaphthacene and 2,3-dihydro-5,12-dihydroxy-1,4-represented by the following formula (IV)
It provides naphthacenequinone.

本発明の化合物(I)〜(IV)は下記のようにして公知
の反応によって合成することができる。
The compounds (I) to (IV) of the present invention can be synthesized by known reactions as described below.

a) 化合物(IV)の合成 1,4−ジヒドロキシ−5,12−ナフタセンキノン(イ)を
水溶性有機溶媒中、水の存在下アルカリ金属炭酸塩とナ
トリウム又はカリウムハイドロサルファイトで処理する
ことによって、2,3−ジヒドロ−5,12−ジヒドロキシ−
1,4−ナフタセンキノン(化合物(IV))が得られる。
a) Synthesis of compound (IV) By treating 1,4-dihydroxy-5,12-naphthacenequinone (a) with an alkali metal carbonate and sodium or potassium hydrosulfite in a water-soluble organic solvent in the presence of water, 2,3-dihydro-5,12-dihydroxy-
1,4-naphthacenequinone (compound (IV)) is obtained.

水溶性有機溶媒としてはアセトン,N−N−ジメチルホル
ムアルデヒド,ジメチルスルホキシド等が挙げられる。
アルカリ金属炭酸塩としては炭酸ナトリウム,炭酸カリ
ウム等が挙げられる。反応温度は0〜100℃、反応時間
は0.5〜10時間の範囲が適当である。
Examples of the water-soluble organic solvent include acetone, NN-dimethylformaldehyde, dimethylsulfoxide and the like.
Examples of alkali metal carbonates include sodium carbonate and potassium carbonate. Suitably, the reaction temperature is 0 to 100 ° C. and the reaction time is 0.5 to 10 hours.

b) 化合物(III)の合成 化合物(IV)を有機溶媒中五塩化リンで処理することに
よって、1,4,5,5,12,12−ヘキサクロロ−5,12−ジヒド
ロナフタレン(化合物(III))が得られる。有機溶媒
としては、ベンゼン,トルエン,キシレン,クロロベン
ゼン,ジクロロベンゼン,1−クロロナフタレン等が挙げ
られる。反応温度は50〜160℃、反応時間は0.5〜50時間
の範囲が適当である。
b) Synthesis of compound (III) By treating compound (IV) with phosphorus pentachloride in an organic solvent, 1,4,5,5,12,12-hexachloro-5,12-dihydronaphthalene (compound (III)) ) Is obtained. Examples of the organic solvent include benzene, toluene, xylene, chlorobenzene, dichlorobenzene and 1-chloronaphthalene. Suitably, the reaction temperature is 50 to 160 ° C. and the reaction time is 0.5 to 50 hours.

c) 化合物(II)の合成 化合物(II)を酢酸溶媒中濃塩酸の存在下二塩化スズで
処理すると、1,4,5,12−テトラクロロナフタセン(化合
物(II))が得られる。反応温度は80〜160℃、反応時
間は0.5〜10時間が適当である。
c) Synthesis of compound (II) When compound (II) is treated with tin dichloride in acetic acid solvent in the presence of concentrated hydrochloric acid, 1,4,5,12-tetrachloronaphthacene (compound (II)) is obtained. A reaction temperature of 80 to 160 ° C. and a reaction time of 0.5 to 10 hours are suitable.

d) 化合物(I)の合成 化合物(II)をN,N−ジメチルホルムアミド中で、ナト
リウム及びセレンで処理するとナフタセノ[1,12−cd:
4,5−c′d′]ビス[1,2]ジセレノール(化合物
(I))が得られる。反応温度は80〜160℃、反応時間
は0.5〜50時間が適当である。化合物(I)はまた化合
物(III)から直接合成することもできる。すなわち化
合物(III)をN,N−ジメチルホルムアミド中でナトリウ
ム及びセレンで処理すると化合物(I)が得られる。反
応温度は80〜160℃、反応時間は0.5〜50時間が適当であ
る。
d) Synthesis of Compound (I) Compound (II) is treated with sodium and selenium in N, N-dimethylformamide to give naphthaceno [1,12-cd:
4,5-c'd '] bis [1,2] diselenol (compound (I)) is obtained. A reaction temperature of 80 to 160 ° C. and a reaction time of 0.5 to 50 hours are suitable. Compound (I) can also be directly synthesized from compound (III). That is, when compound (III) is treated with sodium and selenium in N, N-dimethylformamide, compound (I) is obtained. A reaction temperature of 80 to 160 ° C. and a reaction time of 0.5 to 50 hours are suitable.

e) 電荷移動錯体の合成 化合物(I)を電子供与体とする電荷移動錯体は、化合
物(I)及び電子受容体をそれぞれ室温又は加熱下で溶
媒に溶解した溶液を混合するか、又は化合物(I)と電
子受容体を加熱下溶媒に溶解した溶液を冷却することに
よって得られる。組成比は化合物(I)に対する電子受
容体のモル比で0.25〜5が適当である。
e) Synthesis of Charge Transfer Complex The charge transfer complex having the compound (I) as an electron donor is a mixture of the compound (I) and the electron acceptor dissolved in a solvent at room temperature or under heating, or It is obtained by cooling a solution of I) and an electron acceptor dissolved in a solvent with heating. The composition ratio is preferably 0.25 to 5 in terms of the molar ratio of the electron acceptor to the compound (I).

電子受容体としては、7,7,8,8−テトラシアノキノジメ
タン,2,3,5,6−テトラフルオロ−7,7,8,8−テトラシア
ノキノジメタン,2,5−ジメチル−7,7,8,8−テトラシア
ノキノジメタン,11,11,12,12−テトラシアノ−2,6−ナ
フトキノジメタン,2,3−ジクロロ−5,6−ジシアノベン
ゾキノン,1,1,2,3,4,4−ヘキサアノブタジエン,テトラ
シアノエチレン,ジクロロジシアノベンゾキノン,クロ
ラニル,ブロモアニル,塩素,臭素,ヨウ素,トリヨー
ダイド等が挙げられる。
As the electron acceptor, 7,7,8,8-tetracyanoquinodimethane, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane, 2,5-dimethyl −7,7,8,8-Tetracyanoquinodimethane, 11,11,12,12-Tetracyano-2,6-naphthoquinodimethane, 2,3-Dichloro-5,6-dicyanobenzoquinone, 1,1 Examples include 2,2,3,4,4-hexaanobutadiene, tetracyanoethylene, dichlorodicyanobenzoquinone, chloranil, bromoanil, chlorine, bromine, iodine and triiodide.

有機溶媒としては、ベンゼン,トルエン,キシレン等の
芳香族炭化水素,四塩化炭素,ジクロロメタン,塩化メ
チレン,1,2−ジクロロエタン,1,1,2−トリクロロエタ
ン,1,1,1−トリクロロエタン,ブロモホルム,1,2−ジブ
ロモエタン等のハロゲン化炭化水素或いは二硫化炭素等
が挙げられる。
As the organic solvent, aromatic hydrocarbons such as benzene, toluene, xylene, carbon tetrachloride, dichloromethane, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, 1,1,1-trichloroethane, bromoform, Halogenated hydrocarbons such as 1,2-dibromoethane, carbon disulfide and the like can be mentioned.

(発明の効果) (1) 本発明のナフタセノ[1,12−cd:4,5−c′
d′]ビス[1,2]ジセレノールはTTFより優れた電子供
与性を有する電子供与体である。
(Effects of the Invention) (1) Naphthaceno [1,12-cd: 4,5-c 'of the present invention
d '] bis [1,2] diselenol is an electron donor having an electron donating property superior to that of TTF.

(2) 本発明の新規電子供与体はTSeTより優れた溶解
性を有するだけでなく、これと他成分の電子受容体で形
成される電荷移動錯体は高い導電性を有する。
(2) The novel electron donor of the present invention has not only higher solubility than TSeT, but also the charge transfer complex formed from this and the electron acceptor of the other component has high conductivity.

このように本発明は工業的価値の大きいものということ
ができる。
Thus, the present invention can be said to have great industrial value.

(実施例) 以下本発明を実施例によって具体的に説明するが、本発
明はこれらに限定されるものではない。
(Examples) Hereinafter, the present invention will be specifically described with reference to Examples, but the present invention is not limited thereto.

実施例1 化合物(イ)21g,無水炭酸ナトリウム17.5g,アセトン35
0ml及び水350mlの混合物を1時間攪拌した後、ナトリウ
ムハイドロサルファイト35gを加え、室温で1時間、更
に還流下1時間反応させる。水500mlを加え、生成した
沈澱を集めて乾燥する。得られた沈澱をクロロホルム60
0mlに溶解し、短いシリカゲルカラムを通した後液を
約100mlにまで濃縮し、これをヘキサン200mlで希釈する
と黄色針状結晶として化合物(IV)が得られる(17.0g,
収率80%)。
Example 1 Compound (a) 21 g, anhydrous sodium carbonate 17.5 g, acetone 35
After stirring a mixture of 0 ml and 350 ml of water for 1 hour, 35 g of sodium hydrosulfite was added, and the mixture was reacted at room temperature for 1 hour and further refluxed for 1 hour. 500 ml of water is added and the precipitate formed is collected and dried. Chloroform 60 was added to the obtained precipitate.
After dissolving in 0 ml and passing through a short silica gel column, the solution was concentrated to about 100 ml and diluted with 200 ml of hexane to obtain compound (IV) as yellow needle crystals (17.0 g,
Yield 80%).

化合物(IV)の物性値 融点 230〜232℃ IR 1620cm-1(C=0)1 H−MMR(τ) 3.062(4H,s,CH2),7.60〜7.70(2H,m,芳香族H),8.04
〜8.15(2H,m,芳香族H),8.965(2H,s,芳香族H),14.
122(2H,s,OH) 元素分析 実測値 C73.89,H4.00% C18H12O4としての計算値 C73.97,H4.14% 実施例2 化合物(IV)10g,五塩化リン42.7g及びo−クロロベン
ゼン16mlの混合物を140℃で24時間反応させる。生じた
沈澱を過し、沈澱を石油エーテルで洗浄すると白色プ
リズム状の結晶として化合物(III)が得られる(7.37
g,収率49%)。
Physical properties of compound (IV) Melting point 230 to 232 ° C IR 1620cm -1 (C = 0) 1 H-MMR (τ) 3.062 (4H, s, CH 2 ), 7.60 to 7.70 (2H, m, aromatic H) , 8.04
~ 8.15 (2H, m, aromatic H), 8.965 (2H, s, aromatic H), 14.
122 (2H, s, OH) Elemental analysis Found C73.89, calcd C73.97 as H4.00% C 18 H 12 O 4 , H4.14% Example 2 Compound (IV) 10 g, phosphorus pentachloride A mixture of 42.7 g and 16 ml of o-chlorobenzene is reacted at 140 ° C. for 24 hours. The precipitate formed is washed with and washed with petroleum ether to obtain the compound (III) as white prismatic crystals (7.37).
g, yield 49%).

化合物(III)の物性値 融点 163℃(分解) IR 1560,1590cm-1 1 H−MMR(τ) 6.750(2H,s,芳香族H),7.40〜7.70(4H,m,芳香族
H),7.623(2H,s,芳香族H) MS(m/z) 436(M+),401,366 元素分析 実測値 C49.44 ,H1.77% C18H8Cl6としての計算値 C49.48%,H1.85% 実施例3 化合物(III)7.37g,二塩化スズ水和物26.6g,濃塩酸32.
7ml及び酢酸43.6mlの混合物を2時間攪拌する。水200ml
を加え、生じた沈澱を集め、これをアルミナカラムクロ
マトグラフィーでクロロホルムを溶離液として精製した
後クロロベンゼンで再結晶すると針状結晶として化合物
(II)が得られる(4.90g,収率79%)。
Physical properties melting point 163 ° C. of the compound (III) (decomposition) IR 1560,1590cm -1 1 H-MMR (τ) 6.750 (2H, s, aromatic H), 7.40~7.70 (4H, m , aromatic H), 7.623 (2H, s, aromatic H) MS (m / z) 436 (M +), 401,366 elemental analysis Found C49.44, calcd C49.48% as H1.77% C 18 H 8 Cl 6 , H1.85% Example 3 7.37 g of compound (III), tin dichloride hydrate 26.6 g, concentrated hydrochloric acid 32.
A mixture of 7 ml and 43.6 ml acetic acid is stirred for 2 hours. 200 ml of water
The resulting precipitate is collected, purified by alumina column chromatography using chloroform as an eluent, and recrystallized from chlorobenzene to obtain the compound (II) as needle crystals (4.90 g, yield 79%).

化合物(II)の物性値 融点 257〜259℃ IR 1595,1290,880cm-1 1 H−NMR(τ) 7.408(2H,s,芳香族H),7.50〜7.61(2H,芳香族H),
8.07〜8.18(2H,m,芳香族H),9.307(2H,s,芳香族H) 元素分析 実測値 C59.06,H2.26% C18H8Cl4としての計算値 C59.06,H2.20% 実施例4 N,N−ジメチルホルムアミド50ml中ナトリウム0.202gと
セレン0.695gのサスペンジョンを130℃で2時間攪拌す
る。温度を80℃まで下げた後化合物(II)0.732gを加え
その温度の20時間反応を続ける。室温に冷却した後生じ
た沈澱を集め、水及びアセトンで洗浄し0.1mmHgの減圧
下100℃で乾燥する。
Physical properties mp 257~259 ℃ IR 1595,1290,880cm -1 1 H- NMR of the compound (II) (τ) 7.408 ( 2H, s, aromatic H), 7.50~7.61 (2H, aromatic H),
8.07~8.18 (2H, m, aromatic H), 9.307 (2H, s , aromatic H) Elemental analysis Found C59.06, calculated for H2.26% C 18 H 8 Cl 4 C59.06, H2 .20% Example 4 A suspension of 0.202 g of sodium and 0.695 g of selenium in 50 ml of N, N-dimethylformamide is stirred at 130 ° C. for 2 hours. After lowering the temperature to 80 ° C., 0.732 g of compound (II) is added and the reaction is continued for 20 hours at that temperature. After cooling to room temperature, the precipitate formed is collected, washed with water and acetone, and dried at 100 ° C. under a reduced pressure of 0.1 mmHg.

この沈澱を二硫化炭素を用いてソックスレー抽出を行な
い、抽出物を集め二硫化炭素で再結晶すると深緑色の結
晶として化合物(I)が得られる(0.329g,収率30
%)。
The precipitate was subjected to Soxhlet extraction with carbon disulfide, and the extract was collected and recrystallized with carbon disulfide to obtain compound (I) as dark green crystals (0.329 g, yield 30).
%).

化合物(I)の物性値 融点 300℃ MS(m/z) 542(M+) 元素分析 実測値 C40.28,H1.42% C18H8Se4としての計算値 C40.03,H1.49% 化合物(I)は塩化メチレン,二硫化炭素の溶媒に対
し、TSeTより5倍以上の溶解性を示す。
Compound physical properties mp 300 ° C. MS of (I) (m / z) 542 (M +) Elemental analysis Found C40.28, calculated for H1.42% C 18 H 8 Se 4 C40.03, H1.49 % Compound (I) has a solubility of 5 times or more than TSeT in a solvent of methylene chloride and carbon disulfide.

実施例5 実施例4と同様にして化合物(III)1.09gをN,N−ジメ
チルホルムアミド75ml中ナトリウム0.375gとセレン0.89
6gを用いて80℃で20時間処理すると化合物(I)が得ら
れる(0.275g,収率20%)。
Example 5 In the same manner as in Example 4, 1.09 g of compound (III) was added to 0.375 g of sodium and 0.89 of selenium in 75 ml of N, N-dimethylformamide.
Treatment with 6 g at 80 ° C. for 20 hours gives compound (I) (0.275 g, yield 20%).

参考例6 参考例 化合物(I)についてサイクリックボルタメトリーを行
ない、半波酸化電位を求める結果を第1表に示した。
Reference Example 6 Reference Example Table 1 shows the results of carrying out cyclic voltammetry on the compound (I) and determining the half-wave oxidation potential.

サイクリックボルタメトリーは支持電解質として0.1Mの
テトラブチルアンモニウムパークロレートを含むベンゾ
ニトリル溶液を行い、白金作用電極とAg/AgCl参照電極
を用いた。スキャン速度は100mV/secである。
For cyclic voltammetry, a benzonitrile solution containing 0.1 M tetrabutylammonium perchlorate was used as a supporting electrolyte, and a platinum working electrode and an Ag / AgCl reference electrode were used. The scan speed is 100 mV / sec.

参考例として上記と同様にしてTSeT,TTFの半波酸化電位
を求めた結果を第1表に併せて示した。
As a reference example, the results of obtaining the half-wave oxidation potentials of TSeT and TTF in the same manner as above are also shown in Table 1.

実施例7 化合物(I)と第2表に示した電子受容体を加熱下1,1,
2−トリクロロエタンの飽和溶液とした後冷却して析出
した沈澱を集めて電荷移動錯体を得た。用いた電子受容
体と得られた電荷移動錯体の物性値を第2表に示した。
表中電子受容体の略号の意味は次のとおりである。
Example 7 A compound (I) and an electron acceptor shown in Table 2 were heated under heating 1,1,
After forming a saturated solution of 2-trichloroethane, the mixture was cooled and the deposited precipitates were collected to obtain a charge transfer complex. The physical properties of the electron acceptor used and the resulting charge transfer complex are shown in Table 2.
The abbreviations of electron acceptors in the table have the following meanings.

TCNQ:テトラシアノキノジメタン, TCNQF4:2,3,5,6−テトラフルオロ−7,7,8,8−テトラシ
アノキノジメタン,DMTCNQ:2,5−ジメチル−7,7,8,8−テ
トラシアノキノジメタン,TNAP:11,11,12,12−テトラシ
アノ−2,6−ナフトキノジメタン,TCNE:テトラシアノエ
チレン,DDQ:ジシアノジクロロベンゾキノン,I3:テトラ
ブチルアンモニウムトリヨーダイドから調製したもの。
TCNQ: tetracyanoquinodimethane, TCNQF 4 : 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane, DMTCNQ: 2,5-dimethyl-7,7,8, 8 tetracyanoquinodimethane, TNAP: 11,11,12,12- tetracyano-2,6-naphthoquinonediazide-di methane, TCNE: tetracyanoethylene, DDQ: dicyano dichloro benzoquinone, I 3: tetrabutyl ammonium tri iodide Prepared from.

以上の結果より、化合物(I)を電子供与体としこれと
他成分の電子受容体で形成される電荷移動錯体がTSeTを
電子供与体とするものより優れた導電性を有することが
分る。
From the above results, it can be seen that the charge transfer complex formed of the compound (I) as an electron donor and the electron acceptor of the other component has a higher conductivity than that of the compound having TSeT as an electron donor.

───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 FI 技術表示箇所 C07D 345/00 // C09K 3/00 C 9155−4H ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Internal reference number FI Technical display area C07D 345/00 // C09K 3/00 C 9155-4H

Claims (7)

【特許請求の範囲】[Claims] 【請求項1】下記式(I)で表わされるナフタセノ[1,
12−cd:4,5−c′d′]ビス[1,2]ジセレノール。
1. A naphthaceno [1, represented by the following formula (I):
12-cd: 4,5-c'd '] bis [1,2] diselenol.
【請求項2】下記式(II)で表わされる1,4,5,12−テト
ラクロロナフタセン。
2. A 1,4,5,12-tetrachloronaphthacene represented by the following formula (II).
【請求項3】下記式(III)で表わされる1,4,5,5,12,12
−ヘキサクロロ−5,12−ジヒドロナフタセン。
3. 1,4,5,5,12,12 represented by the following formula (III)
-Hexachloro-5,12-dihydronaphthacene.
【請求項4】下記式(IV)で表わされる2,3−ジヒドロ
−5,12−ジヒドロキシ−1,4−ナフタセンキノン。
4. A 2,3-dihydro-5,12-dihydroxy-1,4-naphthacenequinone represented by the following formula (IV).
【請求項5】請求項1記載のナフタセノ[1,12−cd:4,5
−c′d′]ビス[1,2]ジセレノールを電子供与体と
し、他成分の電子受容体とから導かれた電荷移動錯体。
5. The naftaceno [1,12-cd: 4,5 according to claim 1.
-C'd '] Bis [1,2] diselenol is an electron donor and is a charge transfer complex derived from an electron acceptor of another component.
【請求項6】電子受容体が7,7,8,8−テトラシアノキノ
ジメタン,2,3,5,6−テトラフルオロ−7,7,8,8−テトラ
シアノキノジメタン,2,5−ジメチル−7,7,8,8−テトラ
シアノキノジメタン,11,11,12,12−テトラシアノ−2,6
−ナフトキノジメタン,2,3−ジクロロ−5,6−ジシアノ
ベンゾキノン,1,1,2,3,4,4−ヘキサシアノブタジエン,
テトラシアノエチレン,ジクロロジシアノベンゾキノ
ン,クロラニル,ブロモアニル,塩素,臭素,ヨウ素又
はトリヨーダイドのいずれかである請求項5記載の電荷
移動錯体。
6. The electron acceptor is 7,7,8,8-tetracyanoquinodimethane, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane, 2, 5-Dimethyl-7,7,8,8-tetracyanoquinodimethane, 11,11,12,12-tetracyano-2,6
-Naphthoquinodimethane, 2,3-dichloro-5,6-dicyanobenzoquinone, 1,1,2,3,4,4-hexacyanobutadiene,
The charge transfer complex according to claim 5, which is one of tetracyanoethylene, dichlorodicyanobenzoquinone, chloranil, bromoanil, chlorine, bromine, iodine or triiodide.
【請求項7】電子供与体と電子受容体のモル比が1:0.25
〜5である請求項5又は6記載の電荷移動錯体。
7. The molar ratio of electron donor to electron acceptor is 1: 0.25.
The charge transfer complex according to claim 5 or 6, wherein
JP15844390A 1990-06-15 1990-06-15 Novel tetraselenotetracene and its complex Expired - Lifetime JPH0678300B2 (en)

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