2-thioxonaphth[2,3-d][1,3]dithiol-5,8-dione | 273213-77-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-thioxonaphth[2,3-d][1,3]dithiol-5,8-dione
• 英文别名: 2-Thioxonaphth[2,3-d] [1,3]dithiol-5,8-dione；2-sulfanylidenebenzo[f][1,3]benzodithiole-5,8-dione
• CAS: 273213-77-7
• 化学式: C₁₁H₄O₂S₃
• 分子量: 264.35
• InChiKey: KFVAJYSLZIFIFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  240-242 °C(Solvent: Dichloromethane)
• 沸点：
  541.4±60.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-thioxonaphth[2,3-d][1,3]dithiol-5,8-dione 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 3,13-bis[4,5-bis(pentylsulfanyl)-1,3-dithiol-2-ylidene]-7,9-dithiapentacyclo[13.2.1.02,14.04,12.06,10]octadeca-4,6(10),11,16-tetraene-8-thione
  参考文献：
  名称：

  A novel array in extended tetrathiafulvalenes (TTF): the ‘H’ shape

  摘要：

  The highly extended, cro;ss-conjugated and sulfur rich rr-electron donor 2a was synthesized and characterized introducing the 'H' shape as a new approach in the tetrathiafulvalene (TTF) array. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00107-6
• 作为产物：
  描述：

  1,3-二噻唑-2-硫酮,4,5-二(溴甲基)- 在 四乙基碘化铵 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙腈 为溶剂， 生成 2-thioxonaphth[2,3-d][1,3]dithiol-5,8-dione
  参考文献：
  名称：

  A novel array in extended tetrathiafulvalenes (TTF): the ‘H’ shape

  摘要：

  The highly extended, cro;ss-conjugated and sulfur rich rr-electron donor 2a was synthesized and characterized introducing the 'H' shape as a new approach in the tetrathiafulvalene (TTF) array. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00107-6

文献信息

• Synthesis and Solid‐State Structures of a Tetrathiafulvalene‐Conjugated Bistetracene
  作者：Masataka Yamashita、Daiki Kuzuhara、Naoki Aratani、Hiroko Yamada

  DOI：10.1002/chem.201304997

  日期：2014.5.19

  A tetrathiafulvalene (TTF)‐conjugated bistetracene was synthesized and characterized in the molecular electronic structures based on the spectroscopic measurements and the single‐crystal X‐ray diffraction analysis. UV/Vis absorption and electrochemical measurements of 5 revealed the considerable electronic communication between two tetracenedithiole units by through‐bond and/or through‐space interactions

  合成了四硫富瓦烯（TTF）共轭双硬脂醚，并基于光谱测量和单晶X射线衍射分析在分子电子结构中进行了表征。UV / Vis吸收和5的电化学测量表明，两个四碳二烯单元之间通过键合和/或空间相互作用具有相当大的电子连通性。5的晶体堆积结构不同，表现出多态性，导致各种分子间电子耦合模式。其中，5  A的π堆积结构给出了HOMO的大转移积分（97 meV），该值超出了六并六苯和红荧烯，因此，对于实现高空穴迁移率非常有利。
• [EN] TETRATHIAFULVALENE DERIVATIVE, AND ORGANIC FILM AND ORGANIC TRANSISTOR USING THE SAME<br/>[FR] DÉRIVÉ DE TÉTRATHIAFULVALÈNE ET FILM ORGANIQUE ET TRANSISTOR ORGANIQUE L'UTILISANT
  申请人：RICOH KK

  公开号：WO2010110351A1

  公开（公告）日：2010-09-30

  A tetrathiafulvalene derivative expressed by General Formula (I): General Formula (I) in General Formula (I), X represents an atom selected from a carbon atom, a sulfur atom, and a nitrogen atom, and Xs may be the same or different; provided that when X is the carbon atom or the nitrogen atom, R1 to R8 each represent one of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted thioalkoxy group, and may be the same or different; and Y1 and Y2 each represent one of structures expressed by General Formulas (II) and (III), and may be the same or different: General Formula (II) General Formula (III).

  通用公式（I）表示的四硫富瓦烯衍生物：在通用公式（I）中，X代表从碳原子、硫原子和氮原子中选择的一个原子，Xs可以相同也可以不同；但是当X为碳原子或氮原子时，R1到R8分别代表氢原子、卤素原子、取代或未取代的烷基基团、取代或未取代的烷氧基团、取代或未取代的硫代烷氧基团中的一个，可以相同也可以不同；Y1和Y2分别表示由通用公式（II）和（III）表示的结构中的一个，可以相同也可以不同：通用公式（II）通用公式（III）。
• TETRATHIAFULVALENE DERIVATIVE, AND ORGANIC FILM AND ORGANIC TRANSISTOR USING THE SAME
  申请人：Shinoda Masato

  公开号：US20120035364A1

  公开（公告）日：2012-02-09

  A tetrathiafulvalene derivative expressed by General Formula (I): General Formula (I) in General Formula (I), X represents an atom selected from a carbon atom, a sulfur atom, and a nitrogen atom, and Xs may be the same or different; provided that when X is the carbon atom or the nitrogen atom, R 1 to R 8 each represent one of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted thioalkoxy group, and may be the same or different; and Y 1 and Y 2 each represent one of structures expressed by General Formulas (II) and (III), and may be the same or different: General Formula (II) General Formula (III).

  一种四硫富瓦烯衍生物，由通式（I）表示：在通式（I）中，X代表从碳原子、硫原子和氮原子中选择的一个原子，X可以相同或不同；但当X为碳原子或氮原子时，R1到R8分别代表氢原子、卤素原子、取代或未取代的烷基、取代或未取代的烷氧基和取代或未取代的硫代烷氧基中的一种，可以相同或不同；而Y1和Y2分别代表通式（II）和（III）所表示的结构中的一种，可以相同或不同：通式（II）通式（III）。
• Tetrathiafulvalene derivative, and organic film and organic transistor using the same
  申请人：Shinoda Masato

  公开号：US08530673B2

  公开（公告）日：2013-09-10

  A tetrathiafulvalene derivative expressed by General Formula (I): General Formula (I) in General Formula (I), X represents an atom selected from a carbon atom, a sulfur atom, and a nitrogen atom, and Xs may be the same or different; provided that when X is the carbon atom or the nitrogen atom, R1 to R8 each represent one of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted thioalkoxy group, and may be the same or different; and Y1 and Y2 each represent one of structures expressed by General Formulas (II) and (III), and may be the same or different: General Formula (II) General Formula (III).

  通式（I）表示的四硫富瓦烯衍生物：其中，通式（I）中的X表示从碳原子、硫原子和氮原子中选择的一个原子，X可以相同也可以不同；但是当X为碳原子或氮原子时，R1到R8分别表示氢原子、卤素原子、取代或未取代的烷基、取代或未取代的烷氧基和取代或未取代的硫代烷氧基中的一种，并且可以相同也可以不同；而Y1和Y2分别表示由通式（II）和（III）表示的结构中的一种，可以相同也可以不同：通式（II）通式（III）。
• An electron-deficient tetrathiafulvalene-conjugated bistetracene
  作者：Masataka Yamashita、Hironobu Hayashi、Naoki Aratani、Hiroko Yamada

  DOI：10.1016/j.tetlet.2015.04.080

  日期：2015.6

  An electron-deficient tetrathiafulvalene (TTF)-conjugated bistetracene 2 was synthesized as the counterpart of phenyl-substituted TTF-conjugated bistetracene 1, and was characterized in the molecular electronic structures based on the spectroscopic measurements. UV-vis absorption spectrum of 2 is slightly broader than that of 1 and fluorescence spectrum of 2 is red-shifted, reflecting the red-shifted absorption spectrum. The energy level of the highest occupied molecular orbital (HOMO) of 2 was directly determined by the atmospheric-photoelectron yield spectroscopy in powder to be -5.8 eV, which is remarkably lower than that of 1 (-5.2 eV). (C) 2015 Elsevier Ltd. All rights reserved.