JPH0459762A - N-substituted-2,2'-dipyricyl disulfide-7,7,8,8-teracyanoquinodimethane complex salts and production thereof - Google Patents
N-substituted-2,2'-dipyricyl disulfide-7,7,8,8-teracyanoquinodimethane complex salts and production thereofInfo
- Publication number
- JPH0459762A JPH0459762A JP16899590A JP16899590A JPH0459762A JP H0459762 A JPH0459762 A JP H0459762A JP 16899590 A JP16899590 A JP 16899590A JP 16899590 A JP16899590 A JP 16899590A JP H0459762 A JPH0459762 A JP H0459762A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- tetracyanoquinodimethane
- substituted
- dipyridyl disulfide
- disulfide
- 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 18
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000003242 quaternary ammonium salts Chemical class 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 8
- 230000007935 neutral effect Effects 0.000 claims abstract 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 30
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 238000009835 boiling Methods 0.000 abstract description 4
- 239000004065 semiconductor Substances 0.000 abstract description 4
- 239000012776 electronic material Substances 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 2
- 229910001873 dinitrogen Inorganic materials 0.000 abstract description 2
- 239000011261 inert gas Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 2
- 238000002360 preparation method Methods 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 13
- 238000000034 method Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical compound C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 4
- 239000003990 capacitor Substances 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007784 solid electrolyte Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000004455 differential thermal analysis Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- -1 sulfide quaternary ammonium salts Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 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
- 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
- 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
- 150000002367 halogens Chemical group 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
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000465 moulding 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
- 238000010992 reflux 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
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
［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、特に新組物質としてのＮ−置換−２，２°−
ジピリジルジスルフィド・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 [Field of Industrial Application] The present invention relates to organic semiconductors that are attracting attention as conductive materials in the field of electronic devices or electronic materials, and particularly relates to organic semiconductors that are attracting attention as conductive materials in the field of electronic devices or electronic materials. −2,2°−
The present invention relates to dipyridyl disulfide/7.7,8.8-tetracyanoquinodimethane complex salts and a method for producing the same.
［発明の概要コ
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−２，２°−ジピ
リジルジスルフィド・７，７．８８−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-2,2°-dipyridyl disulfide 7,7.88-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.
下記の式［３］で表わされるＴＣＮＱとただし、式［１
］中、Ｒは０１〜Ｃ＋ａのアルキル基を示す。ｍは１モ
ルの錯塩に含まれる中性７７．８．８−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。TCNQ expressed by the following formula [3] and formula [1]
], R represents an alkyl group of 01 to C+a. m is a positive number (0.5 to 1.5
) means.
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−２，２°−ジピリジルジスル
フィド・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。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-2,2°-dipyridyl disulfide/quaternary ammonium salts represented by the following formula.
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ＣＩ”−ＣＩ８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。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。さら
に、式［２ｊ中のＲは式［１コと同様にＣ３〜Ｃ１８の
アルキル基であり、Ｘはハロゲンである。In the compound of formula [1] above, examples of the alkyl group for R in the formula include methyl, ethyl, propyl, butyl,
Examples include alkyl groups with a carbon number of CI"-CI8 (including all isomers such as n- and 1so-) such as pentyl and hexyl. m in formula [1] is 0.5
~1.5 is preferred, more preferably about 1. Furthermore, R in formula [2j is a C3-C18 alkyl group as in formula [1], and X is a halogen.
［合成方法コ
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−２，２°−ジピリジルジスルフィド・Ｔ
ＣＮＱＣＮ類は、式〔２〕のＮ−１１換−２，２°−ジ
ピリジルジスルフィド・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
収率で製造するスルフィド・第四アンモニウム塩類は既
に公知の化合物であって、２，２°−ジピリジルジスル
フィド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。[Synthesis method] As described above, N-substituted-2,2°-dipyridyl disulfide T, which is a novel compound of formula [1] according to the present invention,
CNQCNs are N-11-substituted-2,2°-dipyridyl disulfide quaternary ammonium salts of formula [2].
The sulfide quaternary ammonium salts which can be easily produced in a favorable yield by reacting with TCNQ of Can be synthesized.
式［３コの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。TCNQ of the formula [3] and various salts thereof, as well as 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.
次に、式［２］の化合物と式［３コの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−２，２°
−ジピリジルジスルフイドヨーダイドの熱アセトニトリ
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。反応生成物はアセトニトリル
、メタノール、エーテルで洗浄しアセトニトリルで再結
晶すると、無機塩類を含有しない式［１］中の一例とし
てのＮ−メチル−２，２゜ジピリジルジスルフィド・Ｔ
ＣＮＱＣＮ上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 [3] will be described in detail.
For example, N-methyl-2,2° as an example in formula [2]
- A hot acetonitrile solution of dipyridyl disulfide iodide and a hot acetonitrile solution of TCNQ of formula [3] are mixed while hot, and 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. When the reaction product is washed with acetonitrile, methanol, and ether and recrystallized with acetonitrile, N-methyl-2,2゜dipyridyl disulfide T as an example of formula [1] containing no inorganic salts is obtained.
It can be obtained in high yield on CNQCN.
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。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に対シテ約
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. The reaction is preferably carried out at the boiling point of an inert organic solvent such as alkyl cellosolve, or a suitable mixture thereof. The amount of TCNQ of formula [3] used in the reaction may be about 1 to 3 moles per mole of the mixture of formula [2]. Further, the amount of the inert organic solvent to be used can be selected as appropriate, such as about 10 to 20 times the amount of the compound of formula [2] and about 50 to 120 times the amount of TCNQ of formula [3]. can be exemplified.
Ｃ実施例】
更に、本発明に係る式［１コのＮ−置換−２゜２°−ジ
ピリジルジスルフィド・ＴＣＮＱＣＮ類の具体的な合成
方法の実施例について述べる。C Example] Further, an example of a specific method for synthesizing the formula [1 N-substituted-2°2°-dipyridyl disulfide/TCNQCN] according to the present invention will be described.
〈実施例１〉
Ｎ−メチル−２，２°−ジピリジルジスルフィド・ＴＣ
ＮＱＣＮ上合成について述べる。<Example 1> N-methyl-2,2°-dipyridyl disulfide/TC
Synthesis on NQCN will be described.
２．２°−ジピリジルジスルフィド４．４０ｇ（２０ｍ
ｍｏｌ）と、溶媒としてエチレングリコールジメチルエ
ーテル１５ｍ１を撹拌溶解した後、ヨウ化メチル（４０
ｍｍｏｌ、２ｅｑ）を加え撹拌しながら６０℃で４８時
間反応させ、反応物を吸引濾過した後エチレングリコー
ルジメチルエーテルで洗浄してＮ−メチル−２，２′−
ジビリジルジスルフイドヨーダイド（融点１５４〜１５
６℃）を５８％の収率で得た。2.2°-dipyridyl disulfide 4.40g (20m
After stirring and dissolving 15 ml of ethylene glycol dimethyl ether as a solvent, methyl iodide (40 mol) was dissolved.
mmol, 2 eq) was added and reacted at 60°C for 48 hours with stirring, and the reaction product was suction filtered and washed with ethylene glycol dimethyl ether to give N-methyl-2,2'-
Dibyridyl disulfide iodide (melting point 154-15
6° C.) was obtained in a yield of 58%.
こうして得たＮ−メチル−２，２−ジビリジルジスルフ
ィドヨーダイド４．０ｍｍｏｌをアセトニトリル２０ｍ
１に沸騰状態で溶解し、別に用意したアセトニトリル６
７ｍ１にＴＣＮＱｏ、９８ｇ （４，８ｍｍｏｌ、１．
２ｅｑ）を沸騰状態で溶解し１時間還流した溶液と熱時
混合した。さらに３０分間還流した後、５℃で２４時間
放置した。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回再結晶を行ない、Ｎ−メチル−２，２°−ジ
ピリジルジスルフィド・ＴＣＮＱＣＮ上融点２１８〜２
４５℃の黒色針状結晶を収率５５％で得ることができた
。4.0 mmol of N-methyl-2,2-dipyridyl disulfide iodide thus obtained was added to 20 ml of acetonitrile.
Dissolve 1 in boiling state and prepare separately acetonitrile 6
7ml of TCNQo, 98g (4.8mmol, 1.
2 eq) was dissolved in a boiling state and mixed with a solution that was refluxed for 1 hour while hot. After refluxing for an additional 30 minutes, the mixture was left at 5° C. for 24 hours. After filtering the precipitated crystals, they were washed with acetonitrile, methanol, and ether in that order, and recrystallized twice with acetonitrile to obtain N-methyl-2,2°-dipyridyl disulfide TCNQCN, melting point 218-2.
Black needle-like crystals at 45° C. could be obtained in a yield of 55%.
得られたＮ−メチル−２，２°−ジピリジルジスルフィ
ド−ＴＣＮＱＣＮ上Ｃ＠Ｎ、Ｈ、、Ｎ 、、Ｓ 、 ）
の元素分析の結果は次の通りである。The resulting N-methyl-2,2°-dipyridyl disulfide-TCNQCN (C@N,H,,N,,S,)
The results of elemental analysis are as follows.
ＨＣＮ
実測値（％） ３．００ ６５．４３ ２１．
９８計算値（％ｌ ２．９７ ６５．３０ ２
１．７６赤外吸収スペクトルを第１図に示す。また示差
熱分析の結果および融解前及び融解後における比抵抗の
四端子法による測定結果を表２に示す。なお、四端子法
はＴＣＮＱ塩約０．１ｇを錠剤成型器に入れ３００ｋｇ
／ｍ”の圧力で直径１０ｍｍのペレットを作り、これに
Ａ％Ｂ、Ｃ％Ｄの４箇のリード線ペレットの周囲に順に
取り付け、定電流発生装置により４０ｕＡの直流電流を
ＡＢ間に流し、そのときのＣＤ間の電位差を電圧計で測
定し、次にＢＣ間にも同様に電流を流してＤＡ間の電位
差を測定する方法である。HCN Actual value (%) 3.00 65.43 21.
98 calculated value (%l 2.97 65.30 2
The 1.76 infrared absorption spectrum is shown in FIG. Further, Table 2 shows the results of differential thermal analysis and the measurement results of specific resistance before and after melting using the four-terminal method. For the four-terminal method, approximately 0.1 g of TCNQ salt is placed in a tablet molding machine and 300 kg is used.
/m'' pressure to make a pellet with a diameter of 10 mm, attach it to the four lead wire pellets of A%B and C%D in order, and apply a direct current of 40 uA between AB using a constant current generator. In this method, the potential difference between CD at that time is measured with a voltmeter, and then a current is similarly passed between BC and the potential difference between DA is measured.
〈実施例２〉
実施例１と同様の手法・手順に準じて表１のような条件
で合成した結果、式［２］中のＲがエチルに置換された
Ｎ−エチル−２，２°−ジピリジルジスルフィドヨーダ
イドを得、さらに実施例１と同様の手法・手順に準じて
、第２表に示すようにＮ−エチル−２，２°−ジピリジ
ルジスルフィド・ＴＣＮＱ錯塩を得た。これらの示差熱
分析結果ならびに比抵抗値を表２に示す。Ｎ−エチル−
２，２°−ジピリジルジスルフィド・ＴＣＮＱ錯塩（実
施例２）の赤外吸収スペクトルを第２図に示す。<Example 2> As a result of synthesis under the conditions shown in Table 1 according to the same method and procedure as in Example 1, N-ethyl-2,2°- in which R in formula [2] was substituted with ethyl was obtained. Dipyridyl disulfide iodide was obtained, and N-ethyl-2,2°-dipyridyl disulfide/TCNQ complex salt was obtained according to the same method and procedure as in Example 1 as shown in Table 2. These differential thermal analysis results and specific resistance values are shown in Table 2. N-ethyl-
The infrared absorption spectrum of 2,2°-dipyridyl disulfide/TCNQ complex salt (Example 2) is shown in FIG.
実施例２（７）ＴＣＮＱ錯塩（ＣｓａＨ＊ｒＮ ＩＱｓ
２ ）の元素分析の結果は次の通りである。Example 2 (7) TCNQ complex salt (CsaH*rN IQs
2) The results of elemental analysis are as follows.
ＨＣＮ
実測値（％１ ３．５５ ６５．２１ ２１．４
４計算値（％１ ３．２２ ６５．７４ ２１．
２９［応用例］
上述のようにして得た式［１］のＮ−置換−２，２°−
ジピリジルジスルフィド・ＴＣＮＱＣＮ類の用途につい
て述べると、このＴＣＮＱＣＮ類は例えば２校のアルミ
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。HCN Actual value (%1 3.55 65.21 21.4
4 Calculated value (%1 3.22 65.74 21.
29 [Application example] N-substitution-2,2°- of formula [1] obtained as described above
Regarding the uses of dipyridyl disulfide/TCNQCN, for example, this TCNQCN can be used as a solid electrolyte in a solid electrolytic capacitor consisting of a capacitor element made of two layers of aluminum foil wrapped with a separator in between, or as a solid electrolyte in a capacitor element made of tantalum powder sintered body. It can be used as a solid electrolyte for a solid electrolytic capacitor consisting of:
第１および２図はこの発明の実施例１および２の錯塩の
赤外吸収スペクトルである。1 and 2 are infrared absorption spectra of the complex salts of Examples 1 and 2 of the present invention.
Claims (2)
−ジピリジルジスルフィド・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＿１＿８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-2,2' represented by the following formula [1]
-Dipyridyl disulfide/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_1_8. m is the neutral 7,7,8,8- contained in 1 mol of complex salt
A positive number corresponding to the number of moles of tetracyanoquinodimethane (
0.5 to 1.5).
−ジピリジルジスルフィド・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−２，２’−ジピ
リジルジスルフィド・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−２，２’−ジピリジル
ジスルフィド・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（Ｏ．５〜１．５）を意味する。 式［１］および式［２］中、ＲはＣ＿１〜Ｃ＿１＿８の
アルキル基を示す。(2) N-substituted-2,2' represented by the following formula [2]
- Dipyridyl disulfide/quaternary ammonium salts are reacted with 7,7,8,8-tetracyanoquinodimethane represented by the following formula [3], ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [3] N-substituted-2,2'-dipyridyl disulfide 7,7,8,8-tetracyanoquinodimethane complex salts represented by the following formula [1] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [1] A method for producing N-substituted-2,2'-dipyridyl disulfide/7,7,8,8-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_1_8.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16899590A JPH0459762A (en) | 1990-06-27 | 1990-06-27 | N-substituted-2,2'-dipyricyl disulfide-7,7,8,8-teracyanoquinodimethane complex salts and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16899590A JPH0459762A (en) | 1990-06-27 | 1990-06-27 | N-substituted-2,2'-dipyricyl disulfide-7,7,8,8-teracyanoquinodimethane complex salts and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0459762A true JPH0459762A (en) | 1992-02-26 |
Family
ID=15878403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16899590A Pending JPH0459762A (en) | 1990-06-27 | 1990-06-27 | N-substituted-2,2'-dipyricyl disulfide-7,7,8,8-teracyanoquinodimethane complex salts and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0459762A (en) |
-
1990
- 1990-06-27 JP JP16899590A patent/JPH0459762A/en active Pending
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