JPH02221249A - N-substituted-2-thiophnealdehyde 1,1-dimethylhydrazone -7,7,8,8-tetracyanoquinodimethane complex salts and production thereof - Google Patents
N-substituted-2-thiophnealdehyde 1,1-dimethylhydrazone -7,7,8,8-tetracyanoquinodimethane complex salts and production thereofInfo
- Publication number
- JPH02221249A JPH02221249A JP4145789A JP4145789A JPH02221249A JP H02221249 A JPH02221249 A JP H02221249A JP 4145789 A JP4145789 A JP 4145789A JP 4145789 A JP4145789 A JP 4145789A JP H02221249 A JPH02221249 A JP H02221249A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- dimethylhydrazone
- substituted
- tetracyanoquinodimethane
- complex salts
- 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 24
- 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 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 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 5
- 239000000126 substance Substances 0.000 claims description 5
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 27
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract description 7
- 239000004065 semiconductor Substances 0.000 abstract description 3
- 238000009835 boiling Methods 0.000 abstract description 2
- 239000004020 conductor Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 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 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000003990 capacitor Substances 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
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 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
- 239000007787 solid Substances 0.000 description 2
- 239000007784 solid electrolyte Substances 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- -1 alkyl cellosolve Chemical compound 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 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
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000007789 gas Substances 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
- KHOZKMBZYAIIDN-UHFFFAOYSA-N n-methyl-n-(thiophen-2-ylmethylideneamino)methanamine Chemical compound CN(C)N=CC1=CC=CS1 KHOZKMBZYAIIDN-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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１
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１．１−ジメチルヒドラゾン・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。
［発明の概要］
更に詳しくは、下記の式［１］で表わされる新規有機半
導体（新規化合物）としてのＮ−置換−２−チオフェン
アルデヒド１．１−ジメチルヒドラゾン・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。
下記の式［３］で表わされるＴＣＮＱとただし、式［１
］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７．７．８．８−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［１］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１
．１−ジメチルヒドラゾン・第四アンモニウム塩類を
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］の化合物において、式中のＲ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−，１ｓｏ−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［１１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［１］と同様にＣ〜Ｃ６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１本発明に係る式［１］の新規化合物で
あるＮ−置換−２−チオフェンアルデヒド１．１−ジメ
チルヒドラゾン・Ｔ ＣＮ Ｑｉｌ塩類は、式［２］の
Ｎ−置換−２−チオフェンアルデヒド１．１−ジメチル
ヒドラゾン・第四アンモニウム塩類を式［３］のＴＣＮ
Ｑ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１．１−ジメチルヒドラゾンＴ
ＣＮ Ｑ１０塩の製造方法について述べる。
式［２］のＮ−置換−２−チオフェンアルデヒド１．１
−ジメチルヒドラゾン・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１．１
−ジメチルヒドラ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−一置換−２−
チオフェンアルデヒド１．１−ジメチルヒドラゾン・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１．１−ジメチルヒドラゾンなｌとし
た場合の反応モル比は１：１〜３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
１．１−ジメチルヒドラゾン・第四アンモニウム塩類の
合成例
式[Industrial Application Field 1] The present invention relates to an organic semiconductor that is attracting attention as a conductive material in the field of electronic devices or electronic materials, and particularly relates to N-substituted-2-thiophene aldehyde 1.1 as a new substance. -Dimethylhydrazone 7.7.
8.8-tetracyanoquinodimethane complex salts and a method for producing the same. [Summary of the Invention] More specifically, N-substituted-2-thiophenealdehyde 1.1-dimethylhydrazone 7.7.8. as a novel organic semiconductor (new compound) represented by the following formula [1].
8-tetracyanoquinodimethane complex salts and a method for producing the same are provided. TCNQ expressed by the following formula [3] and formula [1]
], R represents a C1 to C6 alkyl group; 0m is a positive number (0,5 ~1.5
) means. In addition, for convenience of explanation, 7.7.8.8-tetracyanoquinodimethane is hereinafter referred to as TCNQ. Next, the compound shown by the above formula [1] can be converted to the compound shown by the following formula [2].
] N-substituted-2-thiophene aldehyde 1
．． It can be produced by reacting 1-dimethylhydrazone and quaternary ammonium salts. In the compound of formula [1] above, examples of the alkyl group of R in the formula include methyl, ethyl, propyl, butyl,
Alkyl groups with carbon numbers of C, ~C, such as pentyl and hexyl (including all isomers such as n-, 1so-, etc.)
can be exemplified by formula 0 [m in 11 is 0,5-1
．． 5 is preferred, more preferably about 1. Moreover, R in formula [2] is a C-C6 alkyl group similarly to formula [1], and X is a halogen. [Synthesis method] As described above, N-substituted-2-thiophenaldehyde 1,1-dimethylhydrazone/T CN Qil salts, which are novel compounds of formula [1] according to the present invention, are N- Substituted-2-thiophenaldehyde 1,1-dimethylhydrazone quaternary ammonium salts with TCN of formula [3]
It can be easily produced in a preferred yield by reacting with Q. Below, as a representative example, N-substituted-2
-thiophenaldehyde 1,1-dimethylhydrazone T
The method for producing CN Q10 salt will be described. N-substituted-2-thiophene aldehyde 1.1 of formula [2]
-Dimethylhydrazone/quaternary ammonium salts are already known compounds, including 2-thiophenaldehyde 1.1
It can be easily synthesized from -dimethylhydrazone using a method known per se. This N-monosubstituted-2-
Synthesis examples of thiophenaldehyde 1,1-dimethylhydrazone/quaternary ammonium salts are shown in Table 1. When 1 is 2-thiophenaldehyde 1,1-dimethylhydrazone, the reaction molar ratio is preferably 1:1 to 3. In this example, the ratio was set to 1:1.5. Table 1 Synthetic formula of N-substituted-2-thiophene aldehyde 1,1-dimethylhydrazone/quaternary ammonium salts
【３】のＴＣＮＱお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、Ｒ，Ｍ
ｅｌｂｙらのＪ、Ａｍ、Ｃｈｅｍ、Ｓｏｃ、、８４．３
３７４ （１９６２）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
［１１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１．１−ジメチルヒドラゾン・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Ｔ
ＣＮＱの熱アセトニトリル溶液を熱時混合した後に放冷
し、析出した結晶を濾過する。この際、反応溶液に大過
剰のエーテルを注油し、反応・生成物を析出せしめても
良い６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［１１中の
一例としてのＮ−メチル−２−チオフェンアルデヒド１
．１−ジメチルヒドラゾン・Ｔ ＣＮ Ｑｌｌ塩を好ま
しい収率で得ることができる。
ところで、式［２１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、好ましくは窒素
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と、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０反応に使用する式[3] TCNQ and its various salts and methods for producing the same are already known, for example, R, M
J, Am, Chem, Soc, 84.3 of elby et al.
No. 374 (1962) and Patent Application Publication No. 191414 of 1988. Next, one embodiment of producing the compound of formula [11] 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-thiophenaldehyde 1,1-dimethylhydrazone/quaternary ammonium salt as an example of formula [2] and T of formula [3]
A hot acetonitrile solution of CNQ is mixed while hot, then allowed to cool, and the precipitated crystals are filtered. At this time, a large excess of ether may be added to the reaction solution to precipitate the reaction product.6 The reaction product may be recrystallized with hot acetonitrile, or
Alternatively, if washed with cold absolute ethanol until the coloring of the same ethanol disappears, the formula [N-methyl-2-thiophene aldehyde 1 as an example in 11] which does not contain inorganic salts can be used.
．． 1-dimethylhydrazone.T CN Qll salt can be obtained in a favorable yield. By the way, in the reaction between the compound of formula [21] and TCNQ of formula [3], the reaction is carried out, for example, under normal pressure, preferably in an inert gas atmosphere such as nitrogen gas or argon gas, using acetonitrile, dimethylformamide, tetrahydrofuran, Formulas used for reactions that are preferably carried out at the boiling point of an inert organic solvent such as an alkyl cellosolve or a suitable mixture thereof.
【３】のＴＣＮＱの使用量は、式
［２１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１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１．１−ジメチルヒドラゾン・ＴＣＮＱＣ
Ｎ類の具体的な合成方法の実施例について述べる。
実施例１
Ｎ−メチル−２−チオフェンアルデヒド１． １−ジメ
チルヒドラゾン・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１．１−ジメチ
ルヒドラゾン・第四アンモニウム・沃化水素酸塩０．０
０３０モルをアセトニトリル６０ｍ１に熱時溶解し、こ
れにＴＣＮＱｏ、００３０モルをアセトニトリル４０ｍ
１に熱時溶解して注油し、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。これをさらに乾燥させると、Ｎ−メチル−２
−チオフェンアルデヒド１．ｌ−ジメチルヒドラゾン・
第四アンモニウム・ＴＣＮＱ錯塩、融点２１３〜２１５
℃の針状結晶を収率７３％の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１．ｌ−ジメチルヒドラゾン・第四アンモニウム・Ｔ
ＣＮ Ｑｍ塩の合成について述べたが１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
）、Ｒがｎ−プロピルに置換された化合物（前掲第１表
中３）をそれぞれ用い、実施例１と同様の手法・手順に
準じて合成した結果、Ｎ−エチル−２−チオフェンアル
デヒド１．１−ジメチルヒドラゾン・第四アンモニウム
・ＴＣＮＱ錯塩（実施例２）、Ｎ−ｎ−プロピル−２−
チオフェンアルデヒド１．１−ジメチルヒドラゾン・第
四アンモニウム・ＴＣＮＱ錯塩（実施例３）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
ェンアルデヒド１．１−ジメチルヒドラゾン・ＴＣＮＱ
ＣＮ類の用途について述べると、このＴ ＣＮ Ｑｔｉ
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 amount of TCNQ used in [3] can be exemplified by about 1 to 3 mol per 1 mol of the mixture of formula [21]. In addition, the amount of the inert organic solvent to be used can be selected as appropriate, and is about 10 to 20 times the amount of the compound of formula [2], and about 5 times as much as the TCNQ of formula [3].
An example of the usage amount is 0 to 120 times. [Example] Furthermore, N-substituted-2-thiophenaldehyde 1,1-dimethylhydrazone/TCNQC of formula [1] according to the present invention
An example of a specific method for synthesizing group N will be described. Example 1 N-methyl-2-thiophene aldehyde 1. The synthesis of 1-dimethylhydrazone/quaternary ammonium/TCNQ complex salt will be described. N-Methyl-2-thiophenealdehyde 1.1-dimethylhydrazone/quaternary ammonium/hydriodide 0.0
030 mol was dissolved in 60 ml of acetonitrile while hot, and to this was added TCNQo, 0030 mol was dissolved in 40 ml of acetonitrile.
1 was hot dissolved, oiled, mixed, and further refluxed for 30 minutes. Thereafter, it is left at 5° C. 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 this is further dried, N-methyl-2
-thiophene aldehyde 1. l-dimethylhydrazone・
Quaternary ammonium/TCNQ complex salt, melting point 213-215
℃ needle-like crystals can be obtained with a yield of 73%. Examples 2 to 3 In the above Example 1, N-methyl-2-thiophene aldehyde 1. l-dimethylhydrazone/quaternary ammonium/T
As mentioned above about the synthesis of CN Qm salt, compound R in formula [2] is substituted with ethyl (2 in Table 1 above).
) and a compound in which R was substituted with n-propyl (3 in Table 1 above) were synthesized according to the same method and procedure as in Example 1. As a result, N-ethyl-2-thiophenealdehyde 1. 1-dimethylhydrazone/quaternary ammonium/TCNQ complex salt (Example 2), N-n-propyl-2-
Thiophenaldehyde 1,1-dimethylhydrazone/quaternary ammonium/TCNQ complex salt (Example 3) was obtained. [Application example] N-substituted-2-thiophene aldehyde 1,1-dimethylhydrazone/TCNQ of formula [1] obtained as described above
Regarding the uses of CNs, this T CN Qti
Salts can be used, for example, as the solid electrolyte of a solid electrolytic capacitor consisting of a capacitor element made of two sheets of aluminum foil wound through a separator, or as the solid electrolyte of a solid electrolytic capacitor consisting of a capacitor element of tantalum powder sintered body. It is.
Claims (2)
フェンアルデヒド１，１−ジメチルヒドラゾン・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-thiophenaldehyde 1,1-dimethylhydrazone 7,7 represented by the following formula [1]
, 8,8-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１，１−ジメチルヒドラゾン・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１，１−ジメチルヒドラゾン・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１，１−ジメチルヒドラゾン・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-thiophenaldehyde 1,1-dimethylhydrazone quaternary ammonium salts represented by the following formula [2] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [2] The following formula [3] ] is reacted with 7,7,8,8-tetracyanoquinodimethane, ▲There are mathematical formulas, chemical formulas, tables, etc.▼[3] N-substituted-2-thiophene represented by the following formula [1] Aldehyde 1,1-dimethylhydrazone 7,7,8,
8-tetracyanoquinodimethane complex salts ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [1] N-substituted-2-thiophene aldehyde 1,1-dimethylhydrazone 7,7,8, Method for producing 8-tetracyanoquinodimethane 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 |
|---|---|---|---|
| JP4145789A JPH02221249A (en) | 1989-02-21 | 1989-02-21 | N-substituted-2-thiophnealdehyde 1,1-dimethylhydrazone -7,7,8,8-tetracyanoquinodimethane complex salts and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4145789A JPH02221249A (en) | 1989-02-21 | 1989-02-21 | N-substituted-2-thiophnealdehyde 1,1-dimethylhydrazone -7,7,8,8-tetracyanoquinodimethane complex salts and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02221249A true JPH02221249A (en) | 1990-09-04 |
Family
ID=12608904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4145789A Pending JPH02221249A (en) | 1989-02-21 | 1989-02-21 | N-substituted-2-thiophnealdehyde 1,1-dimethylhydrazone -7,7,8,8-tetracyanoquinodimethane complex salts and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02221249A (en) |
-
1989
- 1989-02-21 JP JP4145789A patent/JPH02221249A/en active Pending
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