JPS63284163A - Tcnq complex - Google Patents
Tcnq complexInfo
- Publication number
- JPS63284163A JPS63284163A JP11577587A JP11577587A JPS63284163A JP S63284163 A JPS63284163 A JP S63284163A JP 11577587 A JP11577587 A JP 11577587A JP 11577587 A JP11577587 A JP 11577587A JP S63284163 A JPS63284163 A JP S63284163A
- Authority
- JP
- Japan
- Prior art keywords
- tcnq
- alkyl
- alkylimidazole
- group
- 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.)
- Pending
Links
- 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 claims abstract description 29
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 150000001768 cations Chemical class 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 18
- 230000007935 neutral effect Effects 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 230000003287 optical effect Effects 0.000 abstract description 3
- 239000007784 solid electrolyte Substances 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 230000006386 memory function Effects 0.000 abstract description 2
- 150000001351 alkyl iodides Chemical class 0.000 abstract 1
- 239000003792 electrolyte Substances 0.000 abstract 1
- 229920005597 polymer membrane Polymers 0.000 abstract 1
- 150000005838 radical anions Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 9
- -1 radical salts Chemical class 0.000 description 7
- 238000005259 measurement Methods 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003990 capacitor Substances 0.000 description 3
- 238000004455 differential thermal analysis Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- IYVYLVCVXXCYRI-UHFFFAOYSA-O hydron;1-propylimidazole Chemical compound CCCN1C=C[NH+]=C1 IYVYLVCVXXCYRI-UHFFFAOYSA-O 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NWXVIUBYBJUOAY-UHFFFAOYSA-N 1,3-dibutylimidazol-1-ium Chemical compound CCCCN1C=C[N+](CCCC)=C1 NWXVIUBYBJUOAY-UHFFFAOYSA-N 0.000 description 1
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 1
- MCMFEZDRQOJKMN-UHFFFAOYSA-O 3-butyl-1h-imidazol-3-ium Chemical compound CCCCN1C=C[NH+]=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-O 0.000 description 1
- KGWVFQAPOGAVRF-UHFFFAOYSA-O 3-hexyl-1h-imidazol-3-ium Chemical compound CCCCCCN1C=C[NH+]=C1 KGWVFQAPOGAVRF-UHFFFAOYSA-O 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、電解コンデンサー、電池、センサー等、電子
材料及び電子部品の素材として、今後広範な用途が開け
ると期待されている？、７．８．８−テトラシアノキノ
ジメタン（以下ＴＣＮＱと称する）の新規な錯体に関す
る。[Detailed Description of the Invention] (Field of Industrial Application) The present invention is expected to find wide application in the future as a material for electronic materials and electronic parts such as electrolytic capacitors, batteries, sensors, etc. , 7.8.8-Tetracyanoquinodimethane (hereinafter referred to as TCNQ).
（従来の技術）
ＴＣＮＱは強力な電子受容性化合物であり、電子供与性
の化合物、例えはピリジン、キノリン、アクリジンある
いは金属類などと容易にラジカル塩を作る。(Prior Art) TCNQ is a strong electron-accepting compound and easily forms radical salts with electron-donating compounds such as pyridine, quinoline, acridine, or metals.
このＴＣＮＱ錯体は、半導体ないし導体域の高い導電性
を持つとともに、加工、成型性の容易さなどの有用な特
徴を持っているために、導電性高分子膜、非線型光学材
料、電解コンデンサー、電池の固体電解質、メモリー機
能を活かしたスイッチング素子等様々な分野にその応用
が期待されている。This TCNQ complex has high conductivity in the semiconductor or conductor region, and has useful features such as ease of processing and moldability, so it can be used in conductive polymer films, nonlinear optical materials, electrolytic capacitors, etc. Applications are expected in a variety of fields, including solid electrolytes for batteries and switching elements that utilize memory functions.
一方これらのＴＣＮＱ錯体の特徴的な物性は、ＴＣＮＱ
に由来することはもちろんであるが、ドナー物質を代え
ることにより変化させてゆくことが可能である。On the other hand, the characteristic physical properties of these TCNQ complexes are that TCNQ
Of course, it is derived from , but it can be changed by changing the donor substance.
一般的なＴＣＮＱ錯体の合成方法は、ヨウ素イオンの還
元反応を利用してドナー物質のカチオンアイオダイドと
中性ＴＣＮＱを反応させることにより錯体を得る方法、
もしくはドナー物質のカチオンクロライドとＴＣＮＱリ
チウム塩を一度反応させたあと中性ＴＣＮＱを反応させ
ることにより錯体を得る方法（Ｄ、Ｓ、Ａｃｋｅｒ、
Ｗ、Ｒ，１Ｉｅｒｔｌｅｒ＋ Ｊ、Ａ＋＋＋。A general method for synthesizing a TCNQ complex is to obtain a complex by reacting a cationic iodide as a donor substance with neutral TCNQ using a reduction reaction of iodine ions;
Alternatively, a method of obtaining a complex by once reacting the cationic chloride of the donor substance with TCNQ lithium salt and then reacting with neutral TCNQ (D, S, Acker,
W, R, 1Iertler+ J, A+++.
Ｃｈｅｍ、Ｓｏｃ、、８４３３７０（１９６２））など
が知られている。Chem, Soc, 843370 (1962)) are known.
（発明が解決しようとする問題点）
前述の如くドナー物質を代えることにより、ＴＣＮＱの
特徴的な物性を変化させることが可能であり、各種のニ
ーズに対して最適な物性を持つＴＣＮＱｌｆ体の開発が
強く望まれている。(Problems to be solved by the invention) As mentioned above, by changing the donor substance, it is possible to change the characteristic physical properties of TCNQ, and to develop TCNQlf bodies with optimal physical properties for various needs. is strongly desired.
本発明は、これらの要請に答えるべく、安価でかつ容易
に合成でき、有機半導体、電子部品、光学材料等への幅
広い応用が期待できる新規なＴＣＮＱ錯体を提供するも
のである。In order to meet these demands, the present invention provides a novel TCNQ complex that is inexpensive and easily synthesized and that can be expected to find wide application in organic semiconductors, electronic components, optical materials, and the like.
（問題点を解決するための手段）
発明者等は、ドナー物質として１−アルキル−３−アル
キルイミダゾールカチオンを使用し、これを中性ＴＣＮ
Ｑと反応させることにより、優れた性質を持つ新規なＴ
ＣＮＱ錯体が得られることを見出し、本発明に至った。(Means for Solving the Problems) The inventors used a 1-alkyl-3-alkylimidazole cation as a donor substance and transferred it to neutral TCN.
By reacting with Q, a new T with excellent properties can be created.
It was discovered that a CNQ complex can be obtained, leading to the present invention.
即ち本発明は、
Ｒ１がｎ−プロピル基またはｎ−ブチル基の時、Ｒ２は
ｎ−プロピル基、ｎ−ブチル基を示す。）
で表される１−アルキル−３−アルキルイミダヅールカ
チオンど、・７．７．８．８−テトラシアノキノジメタ
ンラジカルアニオン（ＴＣＮＱ＝）および中性７．７゜
８．８−テトラシアノキノジメタン（ＴＣＮＱ” ）と
からなる？、７．８．８−テトラシアノキノジメタン錯
体である。That is, in the present invention, when R1 is n-propyl group or n-butyl group, R2 represents n-propyl group or n-butyl group. ), 7.7.8.8-tetracyanoquinodimethane radical anion (TCNQ=) and neutral 7.7°8.8- It is a 7.8.8-tetracyanoquinodimethane complex consisting of tetracyanoquinodimethane (TCNQ'').
本発明のＴＣＮＱ錯体は、下式の如く表すことができる
。The TCNQ complex of the present invention can be represented by the following formula.
コノ式中ｘ、ｙは、錯体中＋７）ＴＣＱＮ＝ （Ｘ）と
ＴＣＮＱ” （Ｙ）の組成比を表し、この錯体組成比
は元素分析や紫外線吸収スペクトルの測定などから決定
することができる。 （例えばＬＭＪｏｓ。In the formula, x and y represent the composition ratio of +7)TCQN= (X) and TCNQ'' (Y) in the complex, and this complex composition ratio can be determined from elemental analysis or ultraviolet absorption spectrum measurement. (For example, LMJos.
ｗｅｒ、 Ｊ、ＩＩａｊｄａ、 Ｊ、Ａｍ、Ｃｈｅｍ、
Ｓｏｃ、、 ９３２５３２（１９７１）などに記載され
た方法による。）
本発明のＴＣＮＱ錯体は、例えばアセトニトリルを溶媒
として、ｌ−アルキル−３−アルキルイミダゾールカチ
オンアイオダイド
このような方法により以下の錯体が合成された。wer, J, IIajda, J, Am, Chem,
Soc, 932532 (1971) and the like. ) The TCNQ complex of the present invention is, for example, l-alkyl-3-alkylimidazole cation iodide using acetonitrile as a solvent.The following complex was synthesized by such a method.
１−エチル−３−メチルイミダゾリウム（７，７，８，
８−テトラシアノキノジメタン）
１．３−ジエチルイミダゾリウム（７，７，８，８−テ
トラシアノキノジメタン）
１−エチル−３−ｎプロピルイミダゾリウム（７，７，
８，８−テトラシアノキノジメタン）
・１−エチル−３−ｎヘキシルイミダゾリウム（７，７
，８，８−テトラシアノキノジメタン）
・１．３−ジｎプロピルイミダゾリウム（７，７，８，
８−テトラシアノキノジメタン）
１−ｎプロピル−３−ｎブチルイミダゾリウム（７，７
，８，８−テトラシアノキノジメタン）
１−ｎブチル−３−ｎプロピルイミダゾリウム（７，７
，８，８−テトラシアノキノジメタン）
１．３−ジｎブチルイミダゾリウム（７，７，８，８−
テトラシアノキノジメタン）
（発明の効果）
このようにして合成された本発明のＴＣＮＱ錯体は、示
差熱分析（ＤＴＡ）の結果より吸熱点および発熱点の両
方を持つために加工、成型性に優れており様々な用途に
適用できるだけでなく、有機半導体コンデンサー用の固
体電解質に単独で使用可能であり、工業利用上存用な錯
体である。1-ethyl-3-methylimidazolium (7,7,8,
8-tetracyanoquinodimethane) 1.3-diethylimidazolium (7,7,8,8-tetracyanoquinodimethane) 1-ethyl-3-n propylimidazolium (7,7,
8,8-tetracyanoquinodimethane) ・1-ethyl-3-n hexylimidazolium (7,7
, 8,8-tetracyanoquinodimethane) ・1,3-di-n-propylimidazolium (7,7,8,
8-tetracyanoquinodimethane) 1-n propyl-3-n butylimidazolium (7,7
,8,8-tetracyanoquinodimethane) 1-n Butyl-3-n Propylimidazolium (7,7
,8,8-tetracyanoquinodimethane) 1,3-di-n-butylimidazolium (7,7,8,8-
Tetracyanoquinodimethane) (Effects of the Invention) Differential thermal analysis (DTA) results show that the TCNQ complex of the present invention synthesized in this manner has both an endothermic point and an exothermic point, which makes it difficult to process and mold. Not only is it excellent and can be applied to a variety of uses, but it can also be used alone as a solid electrolyte for organic semiconductor capacitors, making it an existing complex for industrial use.
以下実施例にて本発明を具体的に説明する。The present invention will be specifically explained below with reference to Examples.
（実施例）
各１−アルキル（１−エチル、ｌ−プロピル、１−ブチ
ル）イミダゾールと１．１倍モルの各アルキル（メチル
、エチル、ｎプロピル、ｎヘキシル）アイオダイドをア
セトニトリル中で混合し、還流下８〜１５時間反応させ
た。(Example) Each 1-alkyl (1-ethyl, l-propyl, 1-butyl) imidazole and 1.1 times the mole of each alkyl (methyl, ethyl, n-propyl, n-hexyl) iodide are mixed in acetonitrile, The reaction was carried out under reflux for 8 to 15 hours.
冷却後、エバポレーターにて低沸物を留去し、残った黄
褐色油状物に適当量のｎ−ヘキサンもしくはジエチルエ
ーテルを添加し、激しく撹拌を加えた。 （この操作に
より直ちに結晶が晶出してくるものと、晶出しないで黄
褐色油状物のまま残るものもがある。）
晶出した結晶は、ｎ−ヘキサンもしくはジエチルエーテ
ルにて良く洗浄した後、必要に応じてエタノール等の適
当な有機溶媒で再結晶して精製を行った。After cooling, low-boiling substances were distilled off using an evaporator, and an appropriate amount of n-hexane or diethyl ether was added to the remaining yellowish brown oil, followed by vigorous stirring. (Some crystals will crystallize immediately after this operation, while others will not crystallize and will remain as a yellowish brown oil.) After washing the crystals that have crystallized thoroughly with n-hexane or diethyl ether, Purification was performed by recrystallization from an appropriate organic solvent such as ethanol, if necessary.
一方、晶出しなかった黄褐色油状物は、上澄み液のｎ−
ヘキサンもしくはジエチルエーテルを捨てた後、再びｎ
−ヘキサンもしくはジエチルエーテルで良く洗浄し、減
圧下で溶媒を留去し乾燥した。On the other hand, the yellowish brown oil that did not crystallize was the n-
After discarding hexane or diethyl ether, n
- Wash thoroughly with hexane or diethyl ether, and dry by distilling off the solvent under reduced pressure.
（２） Ｔ ＣＮ 婁 の合
Ｔ ＣＮ Ｑ１２．３ｇ（６０ミリモル）にアセトニト
リル１４０ｔｓ ｌを加え加熱溶解した後、（１）で得
られた１−アルキル−３−アルキルイミダゾールアイオ
ダイド（仕込みモル比でＴＣＮＱの０．９〜１．８倍ｆ
ｉ）を１０（ｈｎｌのアセトニトリルに溶解して添加し
、１，５〜２．０時間反応を行った。(2) Combination of TCN Q 12.3 g (60 mmol) of TCN Q was added with 140 tsl of acetonitrile and dissolved by heating, and then the 1-alkyl-3-alkylimidazole iodide obtained in (1) (in the charged molar ratio 0.9 to 1.8 times f of TCNQ
i) was dissolved in 10 (hnl) of acetonitrile and added, and the reaction was carried out for 1.5 to 2.0 hours.
反応終了後、冷却、濾過して得られた粗製ＴＣＮＱ錯体
を、２００〜３００ｍ ｌメタノールを用いた還流下１
．０時間の熱洗浄により精製した。After the reaction was completed, the crude TCNQ complex obtained by cooling and filtration was refluxed with 200-300 ml of methanol.
．． Purification was performed by thermal washing for 0 hours.
これにより得られたＴＣＮＱ錯体の収率、物性等を第１
表に示す。The yield, physical properties, etc. of the TCNQ complex thus obtained were evaluated in the first
Shown in the table.
なお、第１表中のＴＣＮＱラジカルアニオン（ＴＣＮＱ
”）と中性ＴＣＮＱ （ＴＣＮＱ’ ）は、前述のｆ！
、Ｍ、Ｋｏｓｗｅｒらの文献に記載された紫外線吸収ス
ペクトル測定方法により測定した。In addition, TCNQ radical anion (TCNQ
”) and the neutral TCNQ (TCNQ') are the f!
, M., Koswer et al.
また、吸熱点および発熱点については、示差熱分析（Ｄ
ＴＡ）により測定した。In addition, for the endothermic point and exothermic point, differential thermal analysis (D
TA).
得られたＴＣＮＱ錯体の’Ｈ−ＮＭＲスペクトルを第１
図〜第８図に示す、このスペクトルの測定条件は、次の
通りである。The 'H-NMR spectrum of the obtained TCNQ complex was
The measurement conditions for this spectrum shown in FIGS. 8 to 8 are as follows.
測定機種：日立 Ｒ−９０Ｈ
測定濃度＝１．２〜１．３χ
測定温度：室温
溶媒：重ジメチルスルホキシド（δ・２．５０ｐｐｍ）
内部標準液ｊＴＭＳ（テトラメチルシラン）積算回数：
１００回Measurement model: Hitachi R-90H Measurement concentration = 1.2 to 1.3χ Measurement temperature: Room temperature Solvent: Heavy dimethyl sulfoxide (δ・2.50ppm)
Internal standard solution jTMS (tetramethylsilane) integration number:
100 times
第１図〜第８図は、本発明のＴ ＣＮ Ｑｔｉｔ体の’
Ｈ−ＮＭＲスペクトルを示す図面である。Figures 1 to 8 show the TCN Qtit body of the present invention.
It is a drawing showing a H-NMR spectrum.
Claims (1)
エチル基、ｎ−プロピル基またはｎ−ブチル基を示し、
Ｒ＿１がエチル基の時、Ｒ＿２はメチル基、エチル基、
ｎ−プロピル基、ｎ−ヘキシル基、 Ｒ＿１がｎ−プロピル基またはｎ−ブチル基の時、Ｒ＿
２はｎ−プロピル基、ｎ−ブチル基を示す） で表される１−アルキル−３−アルキルイミダゾールカ
チオンと、７．７．８．８−テトラシアノキノジメタン
ラジカルアニオン（ＴＣＮＱ■）及び中性７．７．８．
８−テトラシアノキノジメタン（ＴＣＮＱ°）とからな
る７．７．８．８−テトラシアノキノジメタン錯体[Claims] Formula ▲ Numerical formula, chemical formula, table, etc. ▼ (However, R_1 represents an ethyl group, n-propyl group, or n-butyl group,
When R_1 is an ethyl group, R_2 is a methyl group, an ethyl group,
n-propyl group, n-hexyl group, when R_1 is n-propyl group or n-butyl group, R_
2 represents n-propyl group, n-butyl group) 1-alkyl-3-alkylimidazole cation represented by 7.7.8.8-tetracyanoquinodimethane radical anion (TCNQ■) and Sex 7.7.8.
7.7.8.8-tetracyanoquinodimethane complex consisting of 8-tetracyanoquinodimethane (TCNQ°)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11577587A JPS63284163A (en) | 1987-05-14 | 1987-05-14 | Tcnq complex |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11577587A JPS63284163A (en) | 1987-05-14 | 1987-05-14 | Tcnq complex |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63284163A true JPS63284163A (en) | 1988-11-21 |
Family
ID=14670747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11577587A Pending JPS63284163A (en) | 1987-05-14 | 1987-05-14 | Tcnq complex |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63284163A (en) |
-
1987
- 1987-05-14 JP JP11577587A patent/JPS63284163A/en active Pending
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