2-methyl-7,7',8,8'-tetracyanoquinodimethane | 1518-13-4

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 醌二甲烷类
• 英文名称: 2-methyl-7,7',8,8'-tetracyanoquinodimethane
• 英文别名: 2-Methyl-7,7,8,8-tetracyan-chinodimethan-(1,4)；2-Methyl-7,7,8,8-tetracyan-chinodimethan；Methyl-7,7,8,8-tetracyan-p-chinodimethan；Methyl-tetracyano-p-chinodimethan；Propanedinitrile, 2,2'-(2-methyl-2,5-cyclohexadiene-1,4-diylidene)bis-；2-[4-(dicyanomethylidene)-3-methylcyclohexa-2,5-dien-1-ylidene]propanedinitrile
• CAS: 1518-13-4
• 化学式: C₁₃H₆N₄
• 分子量: 218.217
• InChiKey: LAXLKUWCCCBCIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  95.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-7,7',8,8'-tetracyanoquinodimethane 在 sodium iodide 作用下， 以 乙腈 为溶剂， 生成 2-Methyl-1.4-bis-(dicyanmethyl)-benzol
  参考文献：
  名称：

  Substituted Quinodimethans. VII. Substituent and Structural Effects in Cyano-Substituted Quinodimethans

  摘要：

  DOI：

  10.1021/jo01045a054
• 作为产物：
  描述：

  bis(dicyanomethylene)-2-methylcyclohexane 在 吡啶 、 溴 作用下， 生成 2-methyl-7,7',8,8'-tetracyanoquinodimethane
  参考文献：
  名称：

  Russkikh, V. S.; Abashev, G. G., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, # 4, p. 742 - 745

  摘要：

  DOI：

文献信息

• Hydrogen-Bond Interaction in Organic Conductors:  Redox Activation, Molecular Recognition, Structural Regulation, and Proton Transfer in Donor−Acceptor Charge-Transfer Complexes of TTF-Imidazole
  作者：Tsuyoshi Murata、Yasushi Morita、Yumi Yakiyama、Kozo Fukui、Hideki Yamochi、Gunzi Saito、Kazuhiro Nakasuji

  DOI：10.1021/ja072607m

  日期：2007.9.1

  Hydrogen-bond interaction in donor-acceptor charge-transfer complexes of TTF-imidazole demonstrated the electronic effects in terms of control of component ratio and redox activation. These unprecedented effects of hydrogen bonds renewed the criteria giving "a high probability of being organic metals" and produced a number of highly conductive complexes with various acceptors having a wide range of electron-accepting

  TTF-咪唑的供体-受体电荷转移复合物中的氢键相互作用证明了在控制组分比和氧化还原活化方面的电子效应。氢键的这些前所未有的影响更新了“有机金属的可能性很高”的标准，并产生了许多具有各种受电子能力的高导电配合物。在对氯苯醌复合物中，两个分子通过氢键连接并形成 DAD 三联体，将供体-受体组成调节为 2:1。理论计算表明，氢键的极化率控制着供体和对苯醌型受体的氧化还原能力，并在配合物中提供了不同于供体和受体之间氧化还原电位差异所预期的离子性。在对氯苯醌络合物中，这种氢键的电子和结构调控实现了第一个基于氢键功能化 TTF 的金属供体-受体电荷转移络合物。氢键还控制着电荷转移复合物中的分子排列，提供多样化和高度有序的组装结构，对氯苯醌复合物中的 DAD 三元组，I(5) 盐中的一维锯齿形链，氯苯胺酸复合物中的交替供体-受体链和 DADA 环状四聚体在对氨基苯酸复合物中。此外，TTF-咪唑在苯胺酸配
• NOVEL POLYMERIZABLE MONOMER, AND MATERIAL FOR ORGANIC DEVICE, HOLE INJECTION/TRANSPORT MATERIAL, MATERIAL FOR ORGANIC ELECTROLUMINESCENT ELEMENT AND ORGANIC ELECTROLUMINESCENT ELEMENT EACH COMPRISING POLYMER (POLYMERIC COMPOUND) OF THE POLYMERIZABLE MONOMER
  申请人：Eida Mitsuru

  公开号：US20110315964A1

  公开（公告）日：2011-12-29

  A polymerizable monomer represented by the following formula (1) wherein at least one of Ar 1 to Ar 3 is substituted by a group represented by the following formula (2) and which is substituted by one or more groups comprising a polymerizable functional group. Ar 1 to Ar 3 are a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, Ar 6 is a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms and Ar 4 and Ar 5 are a substituted or unsubstituted arylene group having 6 to 40 ring carbon atoms.

  由以下公式（1）表示的可聚合单体，其中Ar1至Ar3中的至少一个被以下公式（2）表示的基团取代，并且被一个或多个包含聚合功能基团的基团取代。Ar1至Ar3是具有6至40个环碳原子的取代或未取代芳基，Ar6是具有6至40个环碳原子的取代或未取代芳基，Ar4和Ar5是具有6至40个环碳原子的取代或未取代芳亚基。
• Crystal Structures, Degree of Charge Transfer, and Non-Linear Optical Characteristics of Intramolecular Charge-Transfer Compounds: Indoline-Substituted Tricyanoquinodimethanes
  作者：Tsuyoshi Murata、Gunzi Saito、Kazukuni Nishimura、Chin-Hong Chong、Masaru Makihara、Genki Honda、Yuichiro Enomoto、Salavat Khasanov、Hideki Yamochi、Akihiro Otsuka、Kenji Kamada、Koji Ohta、Jun Kawamata

  DOI：10.1246/bcsj.81.1131

  日期：2008.9.15

  The substituent effect on the degree of intramolecular charge transfer (δ) and optical properties of donor–π–acceptor compounds comprised of 1,3,3-trimethyl-2-methyleneindoline (I1) and substituted 7,8,8-tricyanoquinodimethane (=2-(4-cyanomethylene-2,5-cyclohexadienylidene)malononitrile, 3CNQ-R, R = substituent groups) moieties were investigated (I1–3CNQ-R). In the crystal structures, I1–3CNQ-R molecules stacked on indoline and/or 3CNQ-R moieties in a head-to-tail manner to cancel their dipole moments and established segregated or mixed stack columnar motifs. The δ values of I1–3CNQ-R molecules in solid and solution states were estimated using the bond length ratio in the crystal structures, molecular orbital calculation, and the solvatochromic shift of intramolecular charge-transfer absorption, respectively, and showed significant and reasonable dependences on substituents of the 3CNQ moiety. Structural analysis revealed that molecular conformation and planarity affect the δ values of I1–3CNQ-R molecules. Molecular orbital calculations revealed that molecular (hyper)polarizabilities can be modulated by tuning δ. I1–3CNQ-R exhibited a solvatochromic shift, and the ground state changed from neutral (δ≤0.5) in less-polar solvents to ionic (δ≥0.5) in polar solvents. Two-photon absorption properties of I1–3CNQ-R showed a significant substituent effect and indicated that δ is a fundamental parameter for modulating non-linear optical properties.

  取代基对由1,3,3-三甲基-2-亚甲基吲哚啉(I1)和取代的7,8,8-三氰基喹诺二甲烷(=2-(4-氰基亚甲基-2,5-环己二烯亚基)丙二腈，3CNQ-R，R=取代基基团)组成的供体-π-受体化合物的分子内电荷转移程度(δ)和光学性质的影响(I1-3CNQ-R)。在晶体结构中，I1-3CNQ-R分子以头对尾的方式堆积在吲哚啉和/或3CNQ-R基团上以消除其偶极矩，并建立了分离或混合的堆叠柱型图案。使用晶体结构中的键长比、分子轨道计算和分子内电荷转移吸收的溶剂化色移分别估计了I1-3CNQ-R分子在固体和溶液状态下的δ值，并显示出对3CNQ基团的取代基的显著和合理的依赖关系。结构分析表明，分子构象和平面性影响I1-3CNQ-R分子的δ值。分子轨道计算表明，通过调节δ可以调节分子的(超)极化率。I1-3CNQ-R表现出溶剂化色移，基态从较低极性溶剂中的中性态(δ≤0.5)变为极性溶剂中的离子态(δ≥0.5)。I1-3CNQ-R的双光子吸收性质显示出显著的取代基效应，表明δ是调节非线性光学性质的基本参数。
• Complex Formation between a Nucleobase and Tetracyanoquinodimethane Derivatives: Crystal Structures and Transport Properties of Charge-Transfer Solids of Cytosine
  作者：Tsuyoshi Murata、Gunzi Saito、Kazukuni Nishimura、Yuichiro Enomoto、Genki Honda、Yasuhito Shimizu、Shogo Matsui、Masafumi Sakata、Olga O. Drozdova、Kyuya Yakushi

  DOI：10.1246/bcsj.81.331

  日期：2008.3.15

  Reaction between cytosine, a nucleobase, in methanol and several 7,7,8,8-tetracyanoquinodimethane derivatives (R-TCNQ) in acetonitrile yielded three kinds of ionic solids; (I) insulators composed o...

  胞嘧啶（一种核碱基）在甲醇中与几种 7,7,8,8-四氰基醌二甲烷衍生物（R-TCNQ）在乙腈中的反应产生三种离子固体；（一）绝缘子组成...
• Molecular Rotors of Coronene in Charge-Transfer Solids
  作者：Yukihiro Yoshida、Yasuhiro Shimizu、Takeshi Yajima、Goro Maruta、Sadamu Takeda、Yoshiaki Nakano、Takaaki Hiramatsu、Hiroshi Kageyama、Hideki Yamochi、Gunzi Saito

  DOI：10.1002/chem.201300578

  日期：2013.9.9

  a DDA‐type alternating π column flanked by another coronene (Cor‐B). Whereas solid‐state 2H NMR spectra of the 1:1 TCNQ complex formed with deuterated coronene confirmed the single in‐plane 6‐fold flipping motion of the coronenes, two unsynchronized motions were confirmed for the 3:1 TCNQ complex, which is consistent with a crystallographic study. Neutral [Ni(mnt)2] (mnt: maleonitriledithiolate) as

  用各种电子受体（A）获得了十种类型的co的中性电荷转移（CT）配合物（电子供体； D）。除了报告的化学计量为1：1的7,7,8,8-四氰基喹二甲烷（TCNQ）配合物和DA型交替π柱外，TCNQ还提供了3：1配合物，其中面对面二聚体在XCNQs之间夹有几束平行的Corones（Cor‐A s），以构建一个DDA型交替π柱，两侧是另一种Coronene（Cor‐B）。固态2由氘化的ron烯形成的1：1 TCNQ配合物的1 H NMR谱图证实了Coronenes的平面内6倍翻转运动，对于3：1 TCNQ配合物证实了两个不同步的运动，这与晶体学研究一致。作为电子受体的中性[Ni（mnt）2 ]（mnt：马来三硫代马来酸）提供了5：2的络合物，其DDA型交替π柱旁接另一个环氧乙烷，类似于3：1 TCNQ络合物。该事实肺心病-A在S [镍（MNT）2 ]络合物在非平行的方式安排必须使的快速平面内旋转心病-A相对于的肺心病-B