tetracyanoquinodimethane | 4032-03-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tetracyanoquinodimethane
• 英文别名: tetracyano-p-quinone；tetracyanoquinone；tetracyano-1,4-benzoquinone；tetracyanobenzoquinone；tetracyano-p-benzochinone；3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarbonitrile
• CAS: 4032-03-5
• 化学式: C₁₀N₄O₂
• 分子量: 208.136
• InChiKey: JNGDCMHTNXRQQD-UHFFFAOYSA-N

物化性质

• 沸点：
  333.6±42.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  tetracyanoquinodimethane 在 9,10-二氢蒽 作用下， 以 乙腈 为溶剂， 生成 2,3,5,6-tetracyanohydroquinone
  参考文献：
  名称：

  Cyanil. Synthesis and characterization of the strongest isolated electron acceptor and its reduced forms

  摘要：

  The strong acceptor tetracyano-1,4-benzoquinone, cyanil, Q[nu(C=N) at 2210 w and 2241 w cm-1; nu(C=O) at 1697 s cm-1 (CH2Cl2); nu(C=C) 1616 s cm-1 (Raman)], as well as tetracyanohydrobenzoquinone, QH2(2241 m and 2263 m cm-1), the radical anion, [Q].-[nu(C=N) approximately 2216 m cm-1 (MeCN)], anion [QH]-, dianions [Q]2- (2185 s cm-1), [H]+[Q]2-, and the dimer dianion [Q]2(2-)(2217 m and 2226 sh cm-1) have been prepared. QH2 was prepared from NaCN and p-bromanil, and Q was prepared from the bromine oxidation of the disilver salt of QH2, QAg2. QAg2 is a versatile synthon for the preparation of Q, [QH]-, [H]+[Q]2-, and [Q]2-. The single-crystal X-ray structures of QH2, Na+[H]+[Q]2-, [Me4N]+[H]+[Q]2-, [Et4N]+[QH]-, [n-Bu4N]+[QH]-, {[Et4N]+}2[Q]2(2-), {[(Ph3P)2N]+}2[Q]2-, Q, [Fe(C5Me5)2].+[H]+[Q]2-, and {[Fe(C5Me5)2].+}2[Q]2(2-) have been determined. The average CO (OC-CCN, and NC-CN) distances are 1.204 (1.488, and 1.338), 1.233 (1.463, and 1.378),1.268 (1.426, and 1.414), and 1.322 (1.413, and 1.372) angstrom for Q, [Q]-, [Q]2-, and QH2, respectively. Several salts exhibit very strong intermolecular hydrogen bonding with O...O separations less than 2.5 angstrom observed for the [Et4N]+[QH]- (2.38 angstrom), [Me4N]+[H]+[Q]2- (2.43 angstrom), and Na+[H]+[Q]2- (2.48 angstrom) salts. (The former is the shortest reported for an an organic system with intermolecular hydrogen bonding.) The degree of protonation varies with counterion with examples of [QH]- and [H]+[Q]2- being observed and strongly influences the electronic and nu(C=N) absorptions. The radical anion was structurally characterized as its diamagnetic dimer dianion, [Q]2(2-), with an intradimer separation of 2.88 angstrom. The EPR of [Q].- in dilute CH2Cl2/MeCN displays hyperfine interaction with four equivalent nitrogens (a(CN) = 0.32 G) and two types of C-13 (2.58 and 5.25 G). Cyanil is the strongest acceptor that has been isolated in the neutral form and has three quasi-reversible one-electron reductions at 0.90,0.09, and -1.81 V vs SCE in MeCN. It is unstable in aqueous media. The reduction potential of cyanil is 0.30 V or more greater than those of DDQ, n-C4(CN)6, and perfluoro-7,7,8,8-tetracyano-p-quinodimethane (TCNQF4). Q dehydrogenates 2,3-dichloro-5,6-dicyanohydroquinone (H2DDQ); thus it is a stronger hydrogen abstraction reagent than conventionally used DDQ. Molecular orbital (ab initio) calculations are in general agreement with the above results, and optimized geometries were used to understand the complex crystal structures.

  DOI：

  10.1021/jo00053a017
• 作为产物：
  描述：

  2,3,5,6-tetracyanohydroquinone 在 溴 、 silver nitrate 作用下， 生成 tetracyanoquinodimethane
  参考文献：
  名称：

  Cyanil. Synthesis and characterization of the strongest isolated electron acceptor and its reduced forms

  摘要：

  The strong acceptor tetracyano-1,4-benzoquinone, cyanil, Q[nu(C=N) at 2210 w and 2241 w cm-1; nu(C=O) at 1697 s cm-1 (CH2Cl2); nu(C=C) 1616 s cm-1 (Raman)], as well as tetracyanohydrobenzoquinone, QH2(2241 m and 2263 m cm-1), the radical anion, [Q].-[nu(C=N) approximately 2216 m cm-1 (MeCN)], anion [QH]-, dianions [Q]2- (2185 s cm-1), [H]+[Q]2-, and the dimer dianion [Q]2(2-)(2217 m and 2226 sh cm-1) have been prepared. QH2 was prepared from NaCN and p-bromanil, and Q was prepared from the bromine oxidation of the disilver salt of QH2, QAg2. QAg2 is a versatile synthon for the preparation of Q, [QH]-, [H]+[Q]2-, and [Q]2-. The single-crystal X-ray structures of QH2, Na+[H]+[Q]2-, [Me4N]+[H]+[Q]2-, [Et4N]+[QH]-, [n-Bu4N]+[QH]-, {[Et4N]+}2[Q]2(2-), {[(Ph3P)2N]+}2[Q]2-, Q, [Fe(C5Me5)2].+[H]+[Q]2-, and {[Fe(C5Me5)2].+}2[Q]2(2-) have been determined. The average CO (OC-CCN, and NC-CN) distances are 1.204 (1.488, and 1.338), 1.233 (1.463, and 1.378),1.268 (1.426, and 1.414), and 1.322 (1.413, and 1.372) angstrom for Q, [Q]-, [Q]2-, and QH2, respectively. Several salts exhibit very strong intermolecular hydrogen bonding with O...O separations less than 2.5 angstrom observed for the [Et4N]+[QH]- (2.38 angstrom), [Me4N]+[H]+[Q]2- (2.43 angstrom), and Na+[H]+[Q]2- (2.48 angstrom) salts. (The former is the shortest reported for an an organic system with intermolecular hydrogen bonding.) The degree of protonation varies with counterion with examples of [QH]- and [H]+[Q]2- being observed and strongly influences the electronic and nu(C=N) absorptions. The radical anion was structurally characterized as its diamagnetic dimer dianion, [Q]2(2-), with an intradimer separation of 2.88 angstrom. The EPR of [Q].- in dilute CH2Cl2/MeCN displays hyperfine interaction with four equivalent nitrogens (a(CN) = 0.32 G) and two types of C-13 (2.58 and 5.25 G). Cyanil is the strongest acceptor that has been isolated in the neutral form and has three quasi-reversible one-electron reductions at 0.90,0.09, and -1.81 V vs SCE in MeCN. It is unstable in aqueous media. The reduction potential of cyanil is 0.30 V or more greater than those of DDQ, n-C4(CN)6, and perfluoro-7,7,8,8-tetracyano-p-quinodimethane (TCNQF4). Q dehydrogenates 2,3-dichloro-5,6-dicyanohydroquinone (H2DDQ); thus it is a stronger hydrogen abstraction reagent than conventionally used DDQ. Molecular orbital (ab initio) calculations are in general agreement with the above results, and optimized geometries were used to understand the complex crystal structures.

  DOI：

  10.1021/jo00053a017

文献信息

• Polyacene derivatives and production thereof
  申请人：——

  公开号：US20030116755A1

  公开（公告）日：2003-06-26

  The present invention relates to polyacene derivatives represented by general formula (I) below: 1 (wherein R 1 to R 10 , etc. each represents hydrogen atom, hydrocarbon group, or an alkoxy group; A 1 and A 2 are hydrogen atom, a halogen atom, a hydrocarbon group, an alkoxy group, cyano group, etc.; n is an integer of not less than 1; R 6 and R 7 may be linked to each other to form a ring); and a process for preparing the polyacene derivatives from polyhydro compounds as well as electrically conductive materials comprising the polyacene derivatives. According to the process for preparing the polyacene derivatives of the present invention, optional substituents can be introduced into any carbon atoms of the polyacene, and the number of aromatic rings can be increased.

  本发明涉及以下通式（I）所代表的聚芳烃衍生物：1（其中R1至R10等分别代表氢原子、烃基或烷氧基；A1和A2分别代表氢原子、卤素原子、烃基、烷氧基、氰基等；n为不小于1的整数；R6和R7可以连接在一起形成环）；以及从聚羟基化合物制备聚芳烃衍生物的方法，以及包括所述聚芳烃衍生物的电导材料。根据本发明的制备聚芳烃衍生物的方法，可以在聚芳烃的任何碳原子上引入可选取代基团，并且可以增加芳香环的数量。
• Charge-transfer complex formations of tetracyanoquinone (cyanil) and aromatic electron donors
  作者：Almaz S. Jalilov、Jianjiang Lu、Jay K. Kochi

  DOI：10.1002/poc.3485

  日期：2016.1

  Single‐electron oxidants are the primary reagents for investigations of the new oxidants and the development of electron‐accepting materials for application in optoelectronics. Quinones are the well‐known class of the neutral single‐electron oxidants. Here, we present the properties of the strongest neutral electron acceptor of this class tetracyanoquinone (cyanil) and investigate its electron‐accepting

  单电子氧化剂是研究新氧化剂以及开发用于光电子学的电子接受材料的主要试剂。醌是众所周知的中性单电子氧化剂。在这里，我们介绍了这类最强的四氰基醌（氰基）中性电子受体的性质，并通过分析与芳族供体分子形成的电荷转移配合物来研究其电子接受强度。四氰基醌与芳香族电子给体的电荷转移络合物在溶液中进行光谱表征，并分离为单晶。版权所有©2015 John Wiley＆Sons，Ltd.
• Oxidation Mechanism of NAD Dimer Model Compounds
  作者：Matthias Patz、Yoshihiro Kuwahara、Tomoyoshi Suenobu、Shunichi Fukuzumi

  DOI：10.1246/cl.1997.567

  日期：1997.6

  The oxidation of a dimeric N-benzyldihydronicotinamide with various oxidants such as quinones, triphenyl carbenium ions and a triplet exited tris(bipyridine) ruthenium(II) complex occurs via initial outer-sphere electron transfer followed by fast C–C bond cleavage and second electron transfer. The kinetic studies allow the determination of the oxidation potential of this compound.

  二聚 N-苄基二氢烟酰胺与各种氧化剂（如醌、三苯基碳鎓离子和三重态三（联吡啶）钌 (II) 络合物的氧化）通过初始外球电子转移随后快速 C-C 键断裂和第二电子发生转移。动力学研究可以确定该化合物的氧化电位。
• FUSED HETEROPOLYCYCLIC COMPOUND, AND METHOD FOR PRODUCING CONDUCTIVE POLYMER IN WHICH SAID COMPOUND IS USED
  申请人：SHOWA DENKO K.K.

  公开号：US20190337919A1

  公开（公告）日：2019-11-07

  The present invention relates to a fused heteropolycyclic compound represented by formulae (1) and (2), a method for producing the same, and a method for producing a conductive polymer represented by formulae (3) and (4) in which at least one compound represented by formula (2) is used (the symbols in the formulae are as described in the description). The method of the present invention is a method for producing a sulfo-group-containing polyisothianaphthene capable of reducing the use amount of an oxidant or capable of being polymerized without the use of any oxidant.

  本发明涉及由式（1）和（2）表示的融合杂多环化合物，其制备方法，以及由式（3）和（4）表示的至少使用一种由式（2）表示的化合物生产的导电聚合物的制备方法（公式中的符号如描述中所述）。本发明的方法是一种生产含有磺酸基的聚异噻纳芘的方法，该方法能够减少氧化剂的使用量或者在不使用任何氧化剂的情况下进行聚合。
• Functional thin film
  申请人：Takahashi Tamotsu

  公开号：US20050240061A1

  公开（公告）日：2005-10-27

  The present invention provides organic electroluminescent elements selected from polyacene derivatives represented by general formula (I) below: [wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , A 1 and A 2 , which are the same or different, each represents hydrogen atom, a hydrocarbon group, etc., and n denotes an integer of not less than 1]. The organic electroluminescent elements of the present invention can provide materials for organic electroluminescent elements and organic electroluminescent elements, which are excellent in stability, durability, luminance and luminance efficiency.

  本发明提供了选择自下述一般式（I）所代表的聚芳烃衍生物的有机电致发光元件：[其中，R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、A1和A2，它们相同或不同，分别代表氢原子、烃基等，n表示不小于1的整数]。本发明的有机电致发光元件可以提供用于有机电致发光元件和有机电致发光元件的材料，这些元件在稳定性、耐久性、亮度和发光效率方面都表现出优异的特性。