JPH01254663A - N-substituted-2,4'-bipyridyl 7,7,8,8-tetracyanoquinodimethane complex salts and production thereof - Google Patents
N-substituted-2,4'-bipyridyl 7,7,8,8-tetracyanoquinodimethane complex salts and production thereofInfo
- Publication number
- JPH01254663A JPH01254663A JP8357588A JP8357588A JPH01254663A JP H01254663 A JPH01254663 A JP H01254663A JP 8357588 A JP8357588 A JP 8357588A JP 8357588 A JP8357588 A JP 8357588A JP H01254663 A JPH01254663 A JP H01254663A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- bipyridyl
- tetracyanoquinodimethane
- substituted
- 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 25
- -1 N-substituted-2,4'-bipyridyl 7,7,8,8-tetracyanoquinodimethane Chemical compound 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 230000007935 neutral effect Effects 0.000 claims abstract description 4
- 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 6
- 239000000126 substance Substances 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 12
- 239000003990 capacitor Substances 0.000 abstract description 5
- 239000004065 semiconductor Substances 0.000 abstract description 4
- 239000007787 solid Substances 0.000 abstract description 3
- 239000007784 solid electrolyte Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 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 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-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
- 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
- 239000000706 filtrate Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 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
- 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
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002367 halogens Chemical group 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
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
[産業上の利用分奸]
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−2,4′−
ビピリジル・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。Detailed Description of the Invention [Industrial Applications] 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 in particular relates to an organic semiconductor that is a novel substance with N-substitution. -2,4'-
The present invention relates to bipyridyl 7,7,8.8-tetracyanoquinodimethane complex salts and a method for producing the same.
[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−2,4−ビピリ
ジル・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。[Summary of the invention] More specifically, N-substituted-2,4-bipyridyl-7,7,8.8-tetracyanoquinodimethane as a novel organic semiconductor (new compound) represented by the following formula [1] The present invention provides complex salts and methods for producing the same.
ル基またはベンジル基を示す。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
。represents a benzyl group or a benzyl group. m means a positive number (0.5 to 1.5) corresponding to the number of moles of neutral 7,7,8.8-tetracyanoquinodimethane contained in 1 mole of the complex salt.
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。In addition, for convenience of explanation, 7,7,8.8-tetracyanoquinodimethane is hereinafter referred to as TCNQ.
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−2,4′−ビピリジル・第四
アンモニウム塩類を
上記の式[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。Next, the compound shown by the above formula [1] can be converted to the compound shown by the following formula [2].
] It can be produced by reacting N-substituted-2,4'-bipyridyl quaternary ammonium salts represented by the above formula [3] with TCNQ represented by the above formula [3].
、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かC1〜C6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。また、式[1]中のRと
してベンジル基を例示することができる。式[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。In the compound of the above formula [1], examples of the alkyl group for R in the formula include alkyl groups having a carbon number or C1 to C6 (n- , 1so-, etc.). Moreover, a benzyl group can be exemplified as R in formula [1]. m in formula [1] is preferably 0.5 to 1.5, more preferably about 1.
また、式[2]中のRは式[1]と同様にC1〜C6の
アルキル基またはベンジル基であり、Xはハロゲンであ
る。Moreover, R in formula [2] is a C1-C6 alkyl group or a benzyl group similarly to formula [1], and X is a halogen.
[合成方法]
上述したように、本発明に係る式[1]の新規化合物で
あるN−置換−2,4′−ビピリジル・TCNQCN類
は1式[2]のN−置換−2,4′−ビピリジル・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、その製造方法について述べる。[Synthesis method] As described above, N-substituted-2,4'-bipyridyl-TCNQCN, which is a novel compound of formula [1] according to the present invention, has N-substituted-2,4'-bipyridyl of formula [2]. -Bipyridyl quaternary ammonium salts can be easily produced in a preferred yield by reacting TCNQ of formula [3]. The manufacturing method will be described below.
式[2]のN−置換−2,4′−ビピリジル・第四アン
モニウム塩類は既に公知の化合物であって、2.4′−
ビピリジル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−2,4−ビピリジ
ル・第四アンそニウム塩類の合成例を第1表に示す。2
.4′−ビピリジルを1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。The N-substituted-2,4'-bipyridyl quaternary ammonium salts of formula [2] are already known compounds, and are 2,4'-bipyridyl quaternary ammonium salts.
It can be easily synthesized from bipyridyl using a method known per se. Synthesis examples of this N-substituted-2,4-bipyridyl quaternary anthonium salt are shown in Table 1. 2
.. When 4'-bipyridyl is 1, the reaction molar ratio is 1:
The ratio is preferably 1 to 3, and in this example, the ratio is 1:1.5.
式[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 (f962)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。TCNQ of formula [3] and various salts thereof and methods for producing the same are already known, for example, R, M
J, Am, Chem, Soc, 84.3 of elby et al.
374 (f962) and Patent Application Publication No. 191414 of 1988.
次に、式[2]の化合物と式[31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1
例えば式[2]中の一例としてのN−メチル−2,4−
ビピリジル・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TCNQ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加し、反応生成物
を析出せしめても良い。反応生成物は熱アセトニトリル
て再結晶するか、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わば、!!!機塩類を含
有しない式[1]中の一例としてのN−メチル−2,4
−ビピリジル・TCNQ錯塩を高収率で得ることができ
る。Next, one embodiment of producing the compound of formula [1] from the compound of formula [2] and TCNQ of formula [31] will be described in detail.
For example, N-methyl-2,4- as an example in formula [2]
A hot acetonitrile solution of bipyridyl quaternary ammonium salts and a hot acetonitrile solution of TCNQ of formula [3] are 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. The reaction product is recrystallized with hot acetonitrile or washed with cold anhydrous ethanol until the ethanol color disappears! ! ! N-methyl-2,4 as an example of formula [1] containing no organic salts
-Bipyridyl/TCNQ complex salt can be obtained in high yield.
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i8
当な混合物のような不活性仔機溶媒の沸点Fで行なうと
良い。反応に使用する式[3]のTCNQの使用量は、
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かできる。また、不活性イ1−機溶
媒の使用【硅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50〜120倍の如き使用量を例示することがで
きる。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 nitrogen gas or argon gas, using acetonitrile, dimethylformamide, or tetrahydrofuran. , alkyl cellosolve, or their i8
It is preferable to use the boiling point F of an inert secondary solvent such as a suitable mixture. The amount of TCNQ of formula [3] used in the reaction is:
For example, the amount used may be about 1 to 3 mol per mol of the mixture of formula [2]. In addition, the use of an inert solvent (silicon) can be selected as appropriate, and is about 10 to 20 times as much as the compound of formula [2] and about 50 to 120 times as much as TCNQ of formula [3]. For example, the usage amount may be as follows.
[実施例]
更に、本発明に係る式[1]のN−置換−2,4′−ビ
ピリジル・rcNQm塩類の具体的な合成方法の実施例
について述べる。[Example] Furthermore, an example of a specific method for synthesizing the N-substituted-2,4'-bipyridyl rcNQm salt of formula [1] according to the present invention will be described.
実rJζ例I
N−メチル−2,4−ビピリジル・第四アンモニウム・
TCNQ錯塩の合成について述べる。Fruit rJζ Example I N-methyl-2,4-bipyridyl quaternary ammonium
The synthesis of TCNQ complex salt will be described.
N−メチル−2,4−ビピリジル・第四アンモニウム・
沃化水素酸塩0.0100モルをアセトニトリル50m
1に熱時溶解し、これにTCNQO,015モルをアセ
トニトリル300m1に熱時溶解して注加し、混合した
後に室温で約5時間放冷する。場合によってはこの放冷
後に大過剰のエーテルを加えて完全に結晶を析出させ、
析出した黒色針状結晶を濾別する。この結晶を熱アセト
ニトリルにより再結晶を繰返し行ない、場合によっては
引続きエタノールで同濾液が着色しなくなるまで洗浄し
た後、エーテルで洗浄し、さらに乾燥させると、沃素イ
オンを全く含有しない純粋なN−メチル−2,4−ビピ
リジル・第四アンモニウム・TCNQ錯塩、融点233
.0〜236゜0℃の黒色針状結晶を収率71%の高収
率で得ることができる。N-methyl-2,4-bipyridyl quaternary ammonium
0.0100 mol of hydroiodide in 50 ml of acetonitrile
To this, 0.15 mol of TCNQO, dissolved in 300 ml of acetonitrile while hot, was added, mixed, and then allowed to cool at room temperature for about 5 hours. In some cases, after this cooling, a large excess of ether is added to completely precipitate the crystals.
The precipitated black needle-like crystals are filtered off. The crystals are repeatedly recrystallized using hot acetonitrile, and in some cases, the filtrate is washed with ethanol until the filtrate is no longer colored, then washed with ether, and further dried to obtain pure N-methyl containing no iodide ions. -2,4-bipyridyl quaternary ammonium TCNQ complex, melting point 233
.. Black needle-shaped crystals having a temperature of 0 to 236°0C can be obtained in a high yield of 71%.
実施例2〜4
上記実施例1ではN−メチル−2,4−ビピリジル・第
四アンモニウム・TCNQ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、n−プロピルおよび
ヘンシルに置換された式[2]の化合物(@掲第1表中
2〜4)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−2,4
′−ビピリジル・第四アンモニウム・TCNQ錯塩(実
施例2)、N−プロピル−2,4′−ビピリジル・第四
アンモニウム・TCNQ錯塩(実施例3)、N−ヘンシ
ル−2,4−ビピリジル・第四アンモニウム・TCNQ
錯塩(実施例4)を得た。Examples 2 to 4 In Example 1 above, the synthesis of N-methyl-2,4-bipyridyl/quaternary ammonium/TCNQ complex salt was described. Using the substituted compounds of formula [2] (@2 to 4 in Table 1), synthesis was performed according to the same method and procedure as in Example 1. As a result, as shown in Table 2, N-ethyl- 2,4
'-Bipyridyl quaternary ammonium TCNQ complex salt (Example 2), N-propyl-2,4'-bipyridyl quaternary ammonium TCNQ complex salt (Example 3), N-hensyl-2,4-bipyridyl quaternary ammonium TCNQ complex salt (Example 3) Tetraammonium/TCNQ
A complex salt (Example 4) was obtained.
第2表にN−アルキル−2,4−ビピリジル・第四アン
モニウム・沃化水素酸塩のモル数とアセトニトリルの量
、TCNQのモル数とアセトニトリルの雀、収率および
融点について、実施例2〜4に実施例1を追加して記す
。Table 2 shows the number of moles of N-alkyl-2,4-bipyridyl quaternary ammonium hydroiodide and the amount of acetonitrile, the number of moles of TCNQ and the amount of acetonitrile, the yield, and the melting point of Examples 2- Example 1 will be added to Section 4.
[応用例]
上述のようにして得た式[1]のN−置換−2,4′−
ビピリジル・TCNQCN類の用途について述べると、
このTCNQCN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。[Application example] N-substituted -2,4'- of formula [1] obtained as described above
Regarding the uses of bipyridyl/TCNQCN,
These TCNQCNs 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 with a separator in between, or as the solid electrolyte of a solid electrolytic capacitor consisting of a capacitor element of tantalum powder sintered body. It's something you get.
Claims (2)
−ビピリジル・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のアルキル基またはベ
ンジル基を示す。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-2,4' represented by the following formula [1]
-Bipyridyl 7,7,8,8-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 or a benzyl group. m is the neutral 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 7,8,8-tetracyanoquinodimethane.
−ビピリジル・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、4′−ビピ
リジル・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−2,4′−ビピリジル
・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、RはC_1〜C_6のアルキル基またはベ
ンジル基を示し、Xはハロゲンを示す。 式[1]中、RはC_1〜C_6のアルキル基またはベ
ンジル基を示す。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
ヨる正の数(0.5〜1.5)を意味する。(2) N-substituted-2,4' represented by the following formula [2]
-Bipyridyl quaternary ammonium salts are reacted with 7,7,8,8-tetracyanoquinodimethane represented by the following formula [3], ▲Mathematical formula, chemical formula, table, etc.▼[2] There are chemical formulas, tables, etc. ▼ [3] N-substituted-2,4'-bipyridyl 7,7,8,8-tetracyanoquinodimethane complex salts represented by the following formula [1] ▲ Mathematical formula, chemical formula , tables, etc. ▼ [1] A method for producing N-substituted-2,4'-bipyridyl 7,7,8,8-tetracyanoquinodimethane complex salts. In formula [2], R represents a C_1 to C_6 alkyl group or a benzyl group, and X represents a halogen. In formula [1], R represents a C_1 to C_6 alkyl group or a benzyl group. m is the neutral 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 7,8,8-tetracyanoquinodimethane.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8357588A JPH01254663A (en) | 1988-04-05 | 1988-04-05 | N-substituted-2,4'-bipyridyl 7,7,8,8-tetracyanoquinodimethane complex salts and production thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8357588A JPH01254663A (en) | 1988-04-05 | 1988-04-05 | N-substituted-2,4'-bipyridyl 7,7,8,8-tetracyanoquinodimethane complex salts and production thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH01254663A true JPH01254663A (en) | 1989-10-11 |
Family
ID=13806304
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP8357588A Pending JPH01254663A (en) | 1988-04-05 | 1988-04-05 | N-substituted-2,4'-bipyridyl 7,7,8,8-tetracyanoquinodimethane complex salts and production thereof |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH01254663A (en) |
-
1988
- 1988-04-05 JP JP8357588A patent/JPH01254663A/en active Pending
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPH01254663A (en) | N-substituted-2,4'-bipyridyl 7,7,8,8-tetracyanoquinodimethane complex salts and production thereof | |
JPH01261370A (en) | N-substituted-4,4'-bipyridyl-7,7,8,8-tetracyanoquinodimethnae complex salts and production thereof | |
JPH01261369A (en) | N-substituted-2-2'-bipyridyl-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof | |
JPH01254662A (en) | N-substituted-2,3'-bipyridyl 7,7,8,8-tetracyanoquinodimethane complex salts and production thereof | |
JPS6377863A (en) | N-substituted-pyrazine-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof | |
JPS63295563A (en) | N-substituted-phthalazine-7,7,8,8-tetracyanoquino-dimethane complex salts and production thereof | |
JPS63239263A (en) | Complex of n-substituted-alkylidene aminoguanidine 7,7,8,8-tetracyanoquinodimethane and its production | |
JPH02215755A (en) | 1-amino-s-methylisothiourea-7,7,8,8-tetracyano-quinodimethane complex salts and production thereof | |
JPS63198667A (en) | N-substituted-quinoxaline 7,7,8,8-tetracyanoquinodimethane complex salts and production thereof | |
JPH02282373A (en) | N-substituted-1,2,3-benzotriazole 7,7,8,8-tetracyanoquinodimethane complex salts and production thereof | |
JPH02215762A (en) | Aminoguanidium-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof | |
JPH02221249A (en) | N-substituted-2-thiophnealdehyde 1,1-dimethylhydrazone -7,7,8,8-tetracyanoquinodimethane complex salts and production thereof | |
JPS6377867A (en) | N-substituted-benzothiazole-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof | |
JPH02282369A (en) | N-substituted-benzimidazole 7,7,8,8-tetracyanoquinodimethane complex and its production | |
JPH02215759A (en) | S-substituted-2-acetylthiophene isothiosemicarbazone-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof | |
JPH02275862A (en) | N-substituted-imidazole 7,7,8,8-tetracyanoquinodimethane complexes and its production | |
JPH02215757A (en) | S-substituted-acetophenone isosemicarbazone-7,7,8,8-tetracyanoquinodimethtane complex salts and production thereof | |
JPH02215763A (en) | 1-amino-3,3-dimethylguanidium-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof | |
JPH02215754A (en) | N-substituted-2-acetylthiophene amidinohydrazone-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof | |
JPH02215758A (en) | N-substituted-2-thiophenealdehyde isothiosemicarbazone-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof | |
JPH02218655A (en) | N-substituted-benzaldehyde 1,1-dimethylhydrazone-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof | |
JPH02282370A (en) | N-substituted-1-methylindole 7,7,8,8-tetracyanoquinodimenthane complex salt and its production | |
JPH02215756A (en) | S-substituted-benzaldehyde thiosemicarbazone-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof | |
JPH02215753A (en) | N-substituted-2-thiophenealdehyde amidinohydrazone-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof | |
JPS6296470A (en) | Novel tcnq complex |