5-[4,5-Bis(hexylsulfanyl)-1,3-dithiol-2-ylidene]-2-[diethoxy(oxido)phosphaniumyl]-[1,3]dithiolo[4,5-d][1,3]dithiole | 934238-71-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 5-[4,5-Bis(hexylsulfanyl)-1,3-dithiol-2-ylidene]-2-[diethoxy(oxido)phosphaniumyl]-[1,3]dithiolo[4,5-d][1,3]dithiole
• 英文别名: 5-[4,5-bis(hexylsulfanyl)-1,3-dithiol-2-ylidene]-2-[diethoxy(oxido)phosphaniumyl]-[1,3]dithiolo[4,5-d][1,3]dithiole
• CAS: 934238-71-8
• 化学式: C₂₃H₃₇O₃PS₈
• 分子量: 649.047
• InChiKey: YJRBFRGXELNMOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  35
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  244
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5-[4,5-Bis(hexylsulfanyl)-1,3-dithiol-2-ylidene]-2-[diethoxy(oxido)phosphaniumyl]-[1,3]dithiolo[4,5-d][1,3]dithiole 、 蒽醌 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以45%的产率得到5-[4,5-Bis(hexylsulfanyl)-1,3-dithiol-2-ylidene]-2-[10-[5-[4,5-bis(hexylsulfanyl)-1,3-dithiol-2-ylidene]-[1,3]dithiolo[4,5-d][1,3]dithiol-2-ylidene]anthracen-9-ylidene]-[1,3]dithiolo[4,5-d][1,3]dithiole
  参考文献：
  名称：

  Tris-融合四硫富瓦烯与蒽醌间隔基一起延伸，作为可充电电池的新正极材料

  摘要：

  获得了由两个四硫富瓦烯（TTF）和一个带有蒽醌间隔基的扩展TTF组成的三融合π电子供体（3）。由结合了未取代和双（乙二氧基）衍生物的正极组成的纽扣型电池的放电容量分别为192和160 mAh g – 1，每个分子涉及六个电子。

  DOI：

  10.1002/ejoc.201801877

文献信息

• Synthesis and Properties of Fused Extended Tetrathiafulvalene Donors with Dithienylmethylene Spacer and Application to Organic Rechargeable Batteries
  作者：Tomokazu Yamauchi、Takashi Kubo、Atsushi Fujioka、Aya Yoshimura、Takashi Shirahata、Hisakazu Miyamoto、Masaru Yao、Yohji Misaki

  DOI：10.1246/bcsj.20210115

  日期：2021.7.15

  Several derivatives of 1,3-dithiole[3]dendralene derivatives with two thiophene spacers (2) were synthesized. The results of an X-ray structure analysis of an analog without fused TTF units and a DFT calculation of the unsubstituted-2 (2Aa) suggested that 2Aa had a structure with significantly distorted between the central 1,3-dithiole (DT) ring and one of the thiophene rings. Cyclic voltammograms

  合成了具有两个噻吩间隔基 ( 2 )的 1,3-二硫醇 [3] 枝烯衍生物的几种衍生物。没有融合 TTF 单元的类似物的 X 射线结构分析结果和未取代的2 ( 2Aa )的 DFT 计算表明2Aa的结构在中心 1,3-二硫醇 (DT) 环和噻吩环之一。四（正己基硫烷基）衍生物（2Be和2Ce）的循环伏安图）由一对双电子氧化还原波和五对单电子氧化还原波组成，对应于七个氧化还原活性 DT 环的存在。四（甲硫基）或双（乙二硫基）衍生物（2Bc或2Bd）作为锂离子电池的正极材料，2Bc /Li和2Bd /Li电池的首次放电容量为133-138 mAh g - 1 .
• Vilsmeier–Haack Type Formylation on 6-Aryl-1,4-dithiafulvenes and Syntheses of Novel Extended Tetrathiafulvalene Donors
  作者：Yohji Misaki、Atsushi Fujioka、Takashi Kubo、Miho Watanabe、Masafumi Ueda、Hisakazu Miyamoto

  DOI：10.1055/s-0035-1560400

  日期：——

  afforded dialdehydes substituted at the 6-position and the furan ring, while the thienyl derivatives and the phenyl derivatives mainly gave monoformylated derivatives substituted at the 6-position. The obtained mono- and dialdehydes were converted into monoaryl-substituted 2,2′-ethanediylidene-bis(1,3-dithiole) derivatives and heteroaromatic ring-inserted [3]dendralene derivatives with triple 1,3-dithiol-2-ylidenes

  摘要 检查了各种6-芳基-1,4-二硫富富烯上的Vilsmeier-Haack型甲酰化。在室温下用过量的POCl 3在DMF中处理的呋喃基衍生物主要提供在6-位取代的二醛和呋喃环，而噻吩基衍生物和苯基衍生物主要提供在6-位取代的单甲酰化衍生物。将获得的单醛和二醛转化为单芳基取代的2,2'-乙二亚甲基-双（1,3-二硫醇）衍生物和杂芳环插入的[3]树枝状烯醛衍生物与三重1,3-二硫醇-2-亚烷基和他们的TTF融合类似物。还通过循环伏安法研究了新的π电子供体的电化学性质。 检查了各种6-芳基-1,4-二硫富富烯上的Vilsmeier-Haack型甲酰化。在室温下用过量的POCl 3在DMF中处理的呋喃基衍生物主要提供在6-位取代的二醛和呋喃环，而噻吩基衍生物和苯基衍生物主要提供在6-位取代的单甲酰化衍生物。将获得的单醛和二醛转化为单芳基取代的2,2'-乙二亚甲基-双（1,3-二硫醇）衍生物和杂
• A Tris-fused Tetrathiafulvalene Extended with Cyclohexene-1,4-diylidene: A New Positive Electrode Material for Organic Rechargeable Batteries
  作者：Minami Kato、Daisuke Ogi、Masaru Yao、Yohji Misaki

  DOI：10.1246/cl.130841

  日期：2013.12.5

  Derivatives of tris-fused TTF donors 3 extended with cyclohexene-1,4-diylidene were synthesized. Cyclic voltammetry revealed that the tetrakis(hexylthio)-3 (3c) exhibited three stages of a two-electron redox process to afford the hexacation. The rechargeable battery incorporating tetrakis(methylsulfanyl)-3 (3b) as the positive electrode material exhibited a high cycle performance in spite of utilizing the highest oxidation state of +6.

  我们合成了由环己烯-1,4-二亚基延伸的三融合 TTF 给体 3 的衍生物。循环伏安法显示，四(甲硫基)-3 (3c)表现出三个阶段的双电子氧化还原过程，从而产生六阳离子。以四(甲硫基)-3 (3b)为正极材料的充电电池尽管使用了 +6 的最高氧化态，但仍表现出很高的循环性能。
• Synthesis and Properties of a New Donor-Acceptor Diad Composed of DT-TTF and Dicyanomethylidene Group
  作者：Yohji Misaki、Ken-ichi Nakamura、Takashi Shirahata、Hisakazu Miyamoto

  DOI：10.3987/com-11-12277

  日期：——

  Several derivatives of a new donor-acceptor diad 1 composed of DT-TTF and dicyanomethylidene group were synthesized. The IR spectra of 1 demonstrated considerable contribution of a polarized structure. Electronic spectra and molecular orbital calculation suggested that the absorption maximum of 1 was due to NHOMO-LUMO transition. Cyclic voltammetry revealed that the compound 1 exhibited three-stage of oxidation and one-stage of reduction processes. The bis(methylthio)-substitudted derivative 1a exhibited conductivity of 10(-6) S cm(-1) in spite of a single-component material.