7,7,8,8-四氰基对苯二醌二甲烷

Tetracyanoquinodimethane (TCNQ)
Ball-and-stick model of the tetracyanoquinodimethane molecule
别名 (2,5-Cyclohexadiene-1,4-diylidene)
-dimalononitrile, 7,7,8,8-Tetracyanoquinodimethane
识别
CAS号 1518-16-7  checkY
PubChem 73697
ChemSpider 66342
SMILES
 
  • c1cc(=C(C#N)C#N)ccc1=C(C#N)C#N
InChI
 
  • 1S/C12H4N4/c13-5-11(6-14)9-1-2-10(4-3-9)12(7-15)8-16/h1-4H
ChEBI 52445
性质
化学式 C12H4N4
摩尔质量 204.19 g/mol g·mol⁻¹
外观 绿色粉末至橙色晶体
熔点 293.5—296 °C（566.6—569.1 K）
沸点 升华
危险性
欧盟分类 未列出
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

7,7,8,8-四氰基对苯二醌二甲烷（缩写：TCNQ）是一种有机化合物，化学式为(NC)2CC6H4C(CN)2。这种多腈（英语：cyanocarbon）是对苯醌的衍生物，为电子受体，用于制备电荷转移配合物，在分子电子学中有所研究。

制备

TCNQ可由1,4-环己二酮（英语：1,4-cyclohexanedione）和丙二腈的缩合反应制备，反应中通过溴脱氢得到二烯：[1]

C6H8O2 + 2 CH2(CN)2 → C6H8(C(CN)2)2 + 2 H2O
C6H8(C(CN)2)2 + 2 Br2 → C6H4(C(CN)2)2 + 4 HBr

它是平面分子，有D2h对称性。[2]

参考文献

维基共享资源上的相关多媒体资源：7,7,8,8-四氰基对苯二醌二甲烷
  1. ^ Acker, Donald S.; Hertler, Walter R. Substituted Quinodimethans. I. Preparation and Chemistry of 7,7,8,8-Tetracyanoquinodimethan. Journal of the American Chemical Society. 1962, 84 (17): 3370. doi:10.1021/ja00876a028. 
  2. ^ Long, Robert E.; Sparks, Robert A.; Trueblood, Kenneth N. The crystal and molecular structure of 7,7,8,8-tetracyanoquinodimethane. Acta Crystallographica. 1965, 18 (5): 932. doi:10.1107/S0365110X65002256. 

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