JPH02215758A - N-substituted-2-thiophenealdehyde isothiosemicarbazone-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof - Google Patents
N-substituted-2-thiophenealdehyde isothiosemicarbazone-7,7,8,8-tetracyanoquinodimethane complex salts and production thereofInfo
- Publication number
- JPH02215758A JPH02215758A JP3585289A JP3585289A JPH02215758A JP H02215758 A JPH02215758 A JP H02215758A JP 3585289 A JP3585289 A JP 3585289A JP 3585289 A JP3585289 A JP 3585289A JP H02215758 A JPH02215758 A JP H02215758A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- isothiosemicarbazone
- thiophenealdehyde
- substituted
- tcnq
- 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
- 150000003839 salts Chemical class 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 230000007935 neutral effect Effects 0.000 claims abstract description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 abstract description 13
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 239000003990 capacitor Substances 0.000 abstract description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract description 6
- 239000004020 conductor Substances 0.000 abstract description 3
- 239000012776 electronic material Substances 0.000 abstract description 3
- 239000011888 foil Substances 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 3
- 239000007784 solid electrolyte Substances 0.000 abstract description 3
- -1 S-substituted-2-thiophenealdehyde isothiosemicarbazone Chemical class 0.000 abstract description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000004804 winding Methods 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- YNTKURSKMLATKI-UHFFFAOYSA-N (thiophen-2-ylmethylideneamino)thiourea Chemical compound NC(=S)NN=CC1=CC=CS1 YNTKURSKMLATKI-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- WFJFGMLKAISFOZ-UHFFFAOYSA-N 1-amino-3-iminourea Chemical compound NN=C(O)N=N WFJFGMLKAISFOZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 150000002344 gold compounds Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
［産業上の利用分野］
本発明は、電子機器分野あるいは電子材料分野などにお
ける導電性材料として注目されている有機半導体に関す
るもので、特に新規物質としてのＮ−置換−２−チオフ
ェンアルデヒドイソチオセミカルバゾン・７，７，８．
８−テトラシアノキノジメタン錯塩類およびその製造方
法に関するものである。[Field of Industrial Application] The present invention relates to an organic semiconductor that is attracting attention as a conductive material in the field of electronic equipment or electronic materials, and in particular, relates to an organic semiconductor that is attracting attention as a conductive material in the field of electronic devices or electronic materials. Carbazone 7, 7, 8.
The present invention relates to 8-tetracyanoquinodimethane complex salts and a method for producing the same.
更に詳しくは、下記の式〔１〕で表わされる新規有機半
導体（ｌｌｒ規化金化合物してのＮ−置換−２−チオフ
ェンアルデヒドインチオセミカルバゾン・７．７．８．
８−テトラシアノキノジメタン錯塩類およびその製造方
法を提供するものである。
ただし、式［１１中、ＲはＣ１〜Ｃ６のアルキル基を示
す０ｍは１モルの錯塩に含まれる中性？、７，８．８−
テトラシアノキノジメタンのモル数に対応する正の数（
０，５〜１．５）を意味する。
なお、説明の便宜上、７．７，８．８−テトラシアノキ
ノジメタンを以下、ＴＣＮＱと称す。
次に、上記の式［１１で示した化合物は、下記の式〔２
〕で表わされるＮ−置換−２−チオフェンアルデヒドイ
ソチオセミカルバゾン・第四アンモニウム塩類を
下記の式［３］で表わされるＴＣＮＱと反応させること
により製造することができるものである。
上記の式［１］の化合物に右いて１式中のＨのアルキル
基の例としては、メチル、エチル、プロピル、ブチル、
ペンチル、ヘキシルのような炭素数がｃ、 〜Ｃ−のア
ルキル基（ｎ−，１８０−などの全ての異性体を含む、
）を例示することができる０式More specifically, a novel organic semiconductor represented by the following formula [1] (N-substituted-2-thiophenealdehyde thiosemicarbazone as a llr-normalized gold compound 7.7.8.
8-tetracyanoquinodimethane complex salts and a method for producing the same are provided. However, in the formula [11, R represents a C1-C6 alkyl group, and 0m is neutral contained in 1 mol of the complex salt. ,7,8.8-
A positive number corresponding to the number of moles of tetracyanoquinodimethane (
0.5 to 1.5). For convenience of explanation, 7,7,8,8-tetracyanoquinodimethane is hereinafter referred to as TCNQ. Next, the compound represented by the above formula [11] is prepared by the following formula [2
] It can be produced by reacting the N-substituted-2-thiophenealdehyde isothiosemicarbazone quaternary ammonium salt represented by the following formula [3] with TCNQ represented by the following formula [3]. Examples of the alkyl group of H in formula 1 in the compound of formula [1] above include methyl, ethyl, propyl, butyl,
Alkyl groups with a carbon number of c, ~C-, such as pentyl and hexyl (including all isomers such as n-, 180-, etc.)
) can be exemplified by 0 expressions
【１】中のｍは０．５〜
１．５が好ましく、より好ましくは約１である。
また、式［２］中のＲは式［ｌ］と同様にＣ〜Ｃ，のア
ルキル基であり、Ｘはハロゲンである。
［合成方法］
上述したように、本発明に係る式［１１の新規化合物で
あるＮ−置換−２−チオフェンアルデヒドイソチオセミ
カルバゾン・ＴＣＮＱＣＮ類は、式［２］のＮ−置換−
２−チオフェンアルデヒドイソチオセミカルバゾン・第
四アンモニウム塩類を式［３］のＴＣＮＱに反応させる
ことによって容易に好ましい収率で製造することができ
る。以下に、代表例としてＮ−置換−２−チオフェンア
ルデヒドインチオセミカルバゾンＴＣＮＱＭ塩の製造方
法について述べる。
式[1] m in the middle is 0.5~
1.5 is preferred, more preferably about 1. Further, R in formula [2] is a C to C alkyl group as in formula [1], and X is a halogen. [Synthesis method] As described above, the N-substituted-2-thiophenaldehyde isothiosemicarbazone/TCNQCN, which is a novel compound of formula [11] according to the present invention, is a compound of N-substituted-2-thiophenealdehyde isothiosemicarbazone/TCNQCN of formula [2]
It can be easily produced in a preferable yield by reacting 2-thiophenealdehyde isothiosemicarbazone/quaternary ammonium salt with TCNQ of formula [3]. A method for producing N-substituted-2-thiophenealdehyde thiosemicarbazone TCNQM salt will be described below as a representative example. formula
【２】のＮ−置換−２−チオフェンアルデヒドイソチ
オセミカルバゾン・第四アンモニウム塩類は既に公知の
化合物であって、２−チオフェンアルデヒドイソチオセ
ミカルバゾンからそれ自体公知の手法を利用して容易に
合成することができる。このＮ−置換−２−チオフヱン
アルデヒドイソチオセミ力ルバゾン・第四アンモニウム
塩類の合成例を第１表に示す、２−チオフェンアルデヒ
ドイソチオセミカルバゾンを１とした場合の反応モル比
はｌ：１〜３が好ましく、本例では１：１．５とした。
第１表
Ｎ−置換−２−チオフェンアルデヒドイソチオセミカル
バゾン・第四アンモニラ・ム塩類の合成例
式［３］のＴＣＮＱｉ３よびその種々の塩ならびにその
製造方法についても既に公知であって、例えばり、Ｒｌ
ＭｅｌｂｙらのＪ、Ａｍ、Ｃｈｅｍ、Ｓｏｃ、、８４．
３３７４ （１９Ｂ２）および昭和５８年特許出願公開
第１９１４１４号公報に明示されている。
次に、式［２］の化合物と式［３］のＴＣＮＱとから式
［１］の化合物を製造する一態様について詳述すると、
例えば式［２］中の一例としてのＮ−メチル−２−チオ
フェンアルデヒドインチオセミカルバゾン・第四アンモ
ニウム塩類の熱アセトニトリル溶液と式［３］のＴＣＮ
Ｑの熱アセトニトリル溶液を熱時混合した後に放冷し、
析出した結晶な濾−する、この際１反応溶液に大過剰の
エーテルを注加し、反応生成物を析出せしめても良い０
反応生成物は熱アセトニトリルで再結晶するか、または
冷無水エタノールで同エタノールの着色が無くなるまで
洗浄すれば、無機塩類を含有しない式［１］中の一例と
してのＮ−メチルー２−チオフエンアルデヒ１
る。
ところで、式［２］の化合物と式［３］のＴＣＮＱとの
反応において、同反応は例えば常圧下、好ましくは童素
ガス、アルゴンガスのような不活性ガス雰囲気中で、ア
セトニトリル、ジメチルホルムアミド、テトラヒドロフ
ラン、アルキルセロソルブなど、あるいはそれらの適当
な混合物のような不活性有機溶媒の沸点下で行なうと良
い１反応に使用する式［３］のＴＣＮＱの使用量は１式
［２］の混合物１モルに対して約１〜３モルの如き使用
量を例示することができる．また、不活性有機溶媒の使
用量も適宜選択することができ、式［２］の化合物に対
して約１０〜２０倍、式［３］のＴＣＮＱに対して約５
０〜１２０倍の如き使用量を例示することができる。
［実施例］
更に、本発明に係る式［１］のＮ−置換−２−チオフェ
ンアルデヒドインチオセミカルバゾン・ＴＣＮＱｔ１塩
類の具体的な合成方法の実施例について述べる。
実施例Ｉ
Ｎ−メチル−２−チオフェンアルデヒドイソチオセミカ
ルバゾン・第四アンモニウム・ＴＣＮＱ錯塩の合成につ
いて述べる。
Ｎ−メチル−２−チオフェンアルデヒドインチオセミカ
ルバゾン・第四アンモニウム・沃化水素酸塩０．００３
０モルをアセトニトリル３０ｍ１に熱時溶解し、これに
ＴＣＮＱｏ．００３０モルをアセトニトリル４０ｍ１に
熱時溶解して注加し、混合し，さらに３０分間還流した
．その後。
約１０時間、５℃に放置する．析出した結晶を濾過した
後，アセトニトリル、メタノール、エーテルの順で洗浄
し，アセトニトリルにより２回再結晶を行なった。
さらに乾燥させると、Ｎ−メチル−２−チオフェンアル
デヒドインチオセミカルバゾン・第四アンモニウム・Ｔ
ＣＮＣ１１塩、融点１９６〜１９９℃の針状結晶を収率
１００％の高収率で得ることができる。
実施例２〜３
上記実施例１ではＮ−メチル−２−チオフェンアルデヒ
ドインチオセミカルバゾン・第四アンモニウム・ＴＣＮ
Ｑ錯塩の合成について述べたが、式【２］中の化合物Ｒ
がエチルに置換された化合物（前掲第１表中２）を用い
、実施例１と同様の手法・手順に準じて合成した結果、
第２表に示すようにＮ−エチル−２−チオフェンアルデ
ヒドイソチオセミカルバゾン・第四アンモニウム・ＴＣ
ＮＱＩ１１塩を得た。
［応用例］
上述のようにして得た式［１］のＮ−置換−２＝チオフ
エンアルデヒドイソチオセミカルバゾン・ＴＣＮＱ＃塩
類の用途について述べると、このＴＣＮＱ鑵塩類は例え
ば２枚のアルミニウム箔をセパレータを介して巻回した
コンデンサ素子からなる固体電解コンデンサの固体電解
質として。
あるいはタンタル粉末焼結体のコンデンサ素子からなる
固体電解コンデンサの固体電解質として利用し得るもの
である。The N-substituted-2-thiophenealdehyde isothiosemicarbazone quaternary ammonium salts of [2] are already known compounds, and can be obtained from 2-thiophenealdehyde isothiosemicarbazone using a method known per se. Can be easily synthesized. Synthesis examples of this N-substituted-2-thiophene aldehyde isothiosemicarbazone/quaternary ammonium salts are shown in Table 1, and the reaction molar ratio when 2-thiophene aldehyde isothiosemicarbazone is 1. It is preferable that l:1 to 3, and in this example, it was set to 1:1.5. Table 1 Synthesis example of N-substituted-2-thiophenealdehyde isothiosemicarbazone quaternary ammonium salts TCNQi3 of formula [3] and various salts thereof and methods for producing the same are already known, such as R, Rl
Melby et al., J. Am. Chem. Soc., 84.
No. 3374 (19B2) and Patent Application Publication No. 191414 of 1988. Next, one embodiment of producing the compound of formula [1] from the compound of formula [2] and TCNQ of formula [3] will be described in detail,
For example, a hot acetonitrile solution of N-methyl-2-thiophenealdehyde thiosemicarbazone quaternary ammonium salt as an example of formula [2] and TCN of formula [3]
After hot mixing the hot acetonitrile solution of Q, let it cool,
Filter the precipitated crystals. In this case, a large excess of ether may be added to the reaction solution to precipitate the reaction product.
If the reaction product is recrystallized with hot acetonitrile or washed with cold anhydrous ethanol until the coloring of the same ethanol disappears, it becomes N-methyl-2-thiophenaldehyde, an example of formula [1], which does not contain inorganic salts. 1. By the way, in the reaction between the compound of formula [2] and TCNQ of formula [3], the reaction is carried out, for example, under normal pressure, preferably in an inert gas atmosphere such as hydrogen gas or argon gas, using acetonitrile, dimethylformamide, It is preferable to carry out the reaction under the boiling point of an inert organic solvent such as tetrahydrofuran, alkyl cellosolve, etc., or a suitable mixture thereof.1 The amount of TCNQ of formula [3] used in the reaction is 1 mole of the mixture of formula [2]. An example of an amount used is about 1 to 3 mol per mol. Further, the amount of the inert organic solvent to be used can be appropriately selected, and is about 10 to 20 times the amount of the compound of formula [2], and about 5 times the amount of TCNQ of the formula [3].
An example of the usage amount is 0 to 120 times. [Example] Further, an example of a specific method for synthesizing the N-substituted-2-thiophenealdehyde thiosemicarbazone/TCNQt1 salt of formula [1] according to the present invention will be described. Example I The synthesis of N-methyl-2-thiophenealdehyde isothiosemicarbazone/quaternary ammonium/TCNQ complex salt will be described. N-Methyl-2-thiophenealdehyde thiosemicarbazone/quaternary ammonium/hydriodide 0.003
0 mol was dissolved in 30 ml of acetonitrile while hot, and TCNQo. 0030 mol was dissolved in 40 ml of acetonitrile while hot and added, mixed and refluxed for further 30 minutes. after that. Leave it at 5℃ for about 10 hours. After filtering the precipitated crystals, they were washed with acetonitrile, methanol, and ether in this order, and recrystallized twice with acetonitrile. When further dried, N-methyl-2-thiophenealdehyde thiosemicarbazone, quaternary ammonium, T
CNC11 salt, needle-like crystals with a melting point of 196-199°C can be obtained in a high yield of 100%. Examples 2 to 3 In Example 1 above, N-methyl-2-thiophenealdehyde thiosemicarbazone/quaternary ammonium/TCN
Although the synthesis of the Q complex salt has been described, the compound R in formula [2]
As a result of synthesis according to the same method and procedure as in Example 1 using a compound in which is substituted with ethyl (2 in Table 1 above),
As shown in Table 2, N-ethyl-2-thiophenealdehyde isothiosemicarbazone/quaternary ammonium/TC
NQI11 salt was obtained. [Application example] Regarding the use of the N-substituted-2=thiophenaldehyde isothiosemicarbazone TCNQ# salts of the formula [1] obtained as described above, this TCNQ salts can be used, for example, to As a solid electrolyte for solid electrolytic capacitors, which consist of a capacitor element made of foil wrapped with a separator in between. Alternatively, it can be used as a solid electrolyte for a solid electrolytic capacitor consisting of a capacitor element made of tantalum powder sintered body.
Claims (2)
フェンアルデヒドイソチオセミカルバゾン・７，７，８
，８−テトラシアノキノジメタン錯塩類。 ▲数式、化学式、表等があります▼［１］ 式［１］中、ＲはＣ＿１〜Ｃ＿６のアルキル基を示す。 ｍは１モルの錯塩に含まれる中性７，７，８，８−テト
ラシアノキノジメタンのモル数に対応する正の数（０．
５〜１．５）を意味する。(1) N-substituted-2-thiophenealdehyde isothiosemicarbazone 7,7,8 represented by the following formula [1]
, 8-tetracyanoquinodimethane complex salts. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [1] In formula [1], R represents an alkyl group of C_1 to C_6. m is a positive number (0.
5 to 1.5).
フェンアルデヒドイソチオセミカルバゾン・第四アンモ
ニウム塩類を ▲数式、化学式、表等があります▼［２］ 下記の式［３］で表わされる７，７，８，８−テトラシ
アノキノジメタンと反応させ、 ▲数式、化学式、表等があります▼［３］ 下記の式［１］で表わされるＮ−置換−２−チオフェン
アルデヒドイソチオセミカルバゾン・７，７，８，８−
テトラシアノキノジメタン錯塩類を▲数式、化学式、表
等があります▼［１］ 得ることを特徴としたＮ−置換−２−チオフェンアルデ
ヒドイソチオセミカルバゾン・７，７，８，８−テトラ
シアノキノジメタン錯塩類の製造方法。 式［２］中、Ｘはハロゲンを示す。 式［１］中、ｍは１モルの錯塩に含まれる中性７，７，
８，８−テトラシアノキノジメタンのモル数に対応する
正の数（０．５〜１．５）を意味する。 式［１］および式［２］中、ＲはＣ＿１〜Ｃ＿６のアル
キル基を示す。(2) N-substituted-2-thiophenealdehyde isothiosemicarbazone quaternary ammonium salts represented by the following formula [2] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [2] The following formula [3] By reacting with 7,7,8,8-tetracyanoquinodimethane represented by Isothiosemicarbazone 7,7,8,8-
N-substituted-2-thiophenealdehyde isothiosemicarbazone 7,7,8,8-tetra characterized by obtaining tetracyanoquinodimethane complex salts ▲Mathematical formulas, chemical formulas, tables, etc.▼ [1] A method for producing cyanoquinodimethane complex salts. In formula [2], X represents halogen. In formula [1], m is neutral 7,7, contained in 1 mol of complex salt.
It means a positive number (0.5 to 1.5) corresponding to the number of moles of 8,8-tetracyanoquinodimethane. In formula [1] and formula [2], R represents an alkyl group of C_1 to C_6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3585289A JPH02215758A (en) | 1989-02-15 | 1989-02-15 | N-substituted-2-thiophenealdehyde isothiosemicarbazone-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3585289A JPH02215758A (en) | 1989-02-15 | 1989-02-15 | N-substituted-2-thiophenealdehyde isothiosemicarbazone-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02215758A true JPH02215758A (en) | 1990-08-28 |
Family
ID=12453524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3585289A Pending JPH02215758A (en) | 1989-02-15 | 1989-02-15 | N-substituted-2-thiophenealdehyde isothiosemicarbazone-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02215758A (en) |
-
1989
- 1989-02-15 JP JP3585289A patent/JPH02215758A/en active Pending
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