5,8-bis(dicyanomethylene)-1,4-dihydro-1,4-ethanonaphthalene | 97516-33-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5,8-bis(dicyanomethylene)-1,4-dihydro-1,4-ethanonaphthalene
• 英文别名: 2-[6-(Dicyanomethylidene)-3-tricyclo[6.2.2.02,7]dodeca-2(7),4,9-trienylidene]propanedinitrile；2-[6-(dicyanomethylidene)-3-tricyclo[6.2.2.02,7]dodeca-2(7),4,9-trienylidene]propanedinitrile
• CAS: 97516-33-1
• 化学式: C₁₈H₁₀N₄
• 分子量: 282.304
• InChiKey: JXHAQRDZQDVVCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  5,8-bis(dicyanomethylene)-1,4-dihydro-1,4-ethanonaphthalene 在 噻吩 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  包含TTF和TCNQ部分的刚性中性分子，其固有的电荷转移和电子转移性质取决于溶剂的极性。

  摘要：

  DOI：

  10.1002/anie.200500812
• 作为产物：
  描述：

  tricyclo[6.2.2.0(2,7)]dodeca-4,9-diene-3,6-dione 在 吡啶 、 manganese(IV) oxide 、 四氯化钛 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 5,8-bis(dicyanomethylene)-1,4-dihydro-1,4-ethanonaphthalene
  参考文献：
  名称：

  包含TTF和TCNQ部分的刚性中性分子，其固有的电荷转移和电子转移性质取决于溶剂的极性。

  摘要：

  DOI：

  10.1002/anie.200500812

文献信息

• Three-Dimensionally-Modified Tetracyanoquinodimethanes and Their Charge-Transfer Complexes with Tetrathiafulvalene Derivatives Having a Wide Range of Ionicity
  作者：Kazuhiro Nakasuji、Masakatsu Nakatsuka、Hideki Yamochi、Ichiro Murata、Shigeharu Harada、Nobutami Kasai、Kimiaki Yamamura、Jiro Tanaka、Gunzi Saito、Toshiaki Enoki、Hiroo Inokuchi

  DOI：10.1246/bcsj.59.207

  日期：1986.1

  Eight different 1:1 charge-transfer(CT) complexes were prepared using tetrahydrobarreleno-tetracyanoquinodimethane(THBTCNQ), dihydrobarreleno-tetracyanoquinodimethane(DHBTCNQ), monobenzobarreleno-tetracyanoquinodimethane(MBBTCNQ), and dibenzobarreleno-tetracyanoquinodimethane(DBBTCNQ) as tetracyanoquinodimethane(TCNQ)-type acceptors, and tetrathiafulvalene(TTF), bis(tetramethyene)-tetrathiafulvalene(OMTTF), and tetramethyl-tetrathiafulvalene(TMTTF) as TTF-type donors. The complexes can be classified into three distinct groups, I–III, on the basis of the magnitude of both the degree of CT and the electrical resistivity of compacted powders. Group-I complexes are characterized by a small band gap semiconductivity and moderate CT, group-II complexes by low conductivity and small CT, and group III complexes by low conductivity and complete CT. The stacking mode of the three groups of complexes are discussed, by comparing the electronic absorption spectra of the three groups of CT complexes with those of the complexes for which the crystal structures are known. A crystal structure analysis of OMTTF–DBBTCNQ revealed that it is the first example of a highly ionic CT complex of a TTF–TCNQ type with a regular mixed stacking mode. These three groups of complexes containing bulky acceptor groups will be of theoretical interest in studying the crystal properties of organic CT complexes.

  制备了八种不同的1:1电荷转移（CT）复合物，使用四氢巴伦烯-四氰基喹啉二甲烷（THBTCNQ）、二氢巴伦烯-四氰基喹啉二甲烷（DHBTCNQ）、单苯巴伦烯-四氰基喹啉二甲烷（MBBTCNQ）和二苯巴伦烯-四氰基喹啉二甲烷（DBBTCNQ）作为TCNQ型受体，四硫富瓦烯（TTF）、双（四甲烯）-四硫富瓦烯（OMTTF）和四甲基-四硫富瓦烯（TMTTF）作为TTF型施体。这些复合物可根据CT程度和压缩粉末的电阻率大小分为三组：I–III。I组复合物具有小带隙半导体特性和中等的CT，II组复合物表现为低导电性和小CT，而III组复合物则具有低导电性和完全CT。通过比较这三组CT复合物的电子吸收光谱与已知晶体结构复合物的光谱，讨论了这三组复合物的堆叠模式。对OMTTF–DBBTCNQ的晶体结构分析表明，它是第一例具有规则混合堆叠模式的高离子CT复合物，属于TTF–TCNQ类型。这三组含有庞大受体基团的复合物在研究有机CT复合物的晶体特性方面具有理论意义。
• ORGANIC ELECTROLUMINESCENT ELEMENT
  申请人：Konica Minolta, Inc.

  公开号：US20150076469A1

  公开（公告）日：2015-03-19

  The organic electroluminescent element has a pair of electrodes and at least two organic functional layers including a light-emitting layer on a substrate. The light-emitting layer contains a host compound and a phosphorescent dopant. The light-emitting layer or the layer adjacent to the light-emitting layer contains quantum dots.
• US9972802B2
  申请人：——

  公开号：US9972802B2

  公开（公告）日：2018-05-15
• A Rigid Neutral Molecule Involving TTF and TCNQ Moieties with Intrinsic Charge- and Electron-Transfer Properties that Depend on the Polarity of the Solvent
  作者：Evgeny Tsiperman、James Y. Becker、Vladimir Khodorkovsky、Alex Shames、Lev Shapiro

  DOI：10.1002/anie.200500812

  日期：2005.6.27