2-[10-[4,5-Bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-2,6-diethynylanthracen-9-ylidene]-4,5-bis(methylsulfanyl)-1,3-dithiole | 913337-43-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-[10-[4,5-Bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-2,6-diethynylanthracen-9-ylidene]-4,5-bis(methylsulfanyl)-1,3-dithiole
• 英文别名: 2-[10-[4,5-bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-2,6-diethynylanthracen-9-ylidene]-4,5-bis(methylsulfanyl)-1,3-dithiole
• CAS: 913337-43-6
• 化学式: C₂₈H₂₀S₈
• 分子量: 612.995
• InChiKey: RGUOSYYKUBGDCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  202
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[10-[4,5-Bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-2,6-diethynylanthracen-9-ylidene]-4,5-bis(methylsulfanyl)-1,3-dithiole 、 2-iodo-anthraquinone 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以50%的产率得到2-[2-[9,10-Bis[4,5-bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-6-[2-(9,10-dioxoanthracen-2-yl)ethynyl]anthracen-2-yl]ethynyl]anthracene-9,10-dione
  参考文献：
  名称：

  Synthesis and Electronic Properties of a Conjugated TTFAQ Trimer and Donor-Acceptor Ensembles of TTFAQ and Anthraquinone

  摘要：

  我们报告了利用 Sonogashira 反应和 Horner-Wadsworth-Emmons 反应首次合成的共轭 TTFAQ 三聚体以及两种基于 TTFAQ-蒽醌的供体-受体组合物。介绍了这些化合物的电子吸收和电化学氧化还原特性。

  DOI：

  10.1055/s-2008-1032040
• 作为产物：
  描述：

  2,6-二溴蒽醌 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 正丁基锂 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.75h， 生成 2-[10-[4,5-Bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-2,6-diethynylanthracen-9-ylidene]-4,5-bis(methylsulfanyl)-1,3-dithiole
  参考文献：
  名称：

  Synthesis and electronic properties of alkyne–TTFAQ based molecular wires

  摘要：

  We herein describe the first synthesis of a series of pi-extend tetrathiafulvalene and alkyne based conjugated molecular wires. Electronic properties of these compounds were characterized by cyclic voltammetry, UV-vis absorption, and fluorescence spectroscopy. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.090

文献信息

• TTFAQ-cored D/A ensembles: synthesis, electronic properties, and redox responses to transition metal ions
  作者：Min Shao、Yuming Zhao

  DOI：10.1016/j.tetlet.2010.03.099

  日期：2010.5

  anthraquinone-type π-extended tetrathiafulvalene (TTFAQ)-cored D/A triads were synthesized and characterized by UV–vis absorption and cyclic voltammetric analyses. Electronic substituent effects were unraveled by making a comparison with analogous TTFAQ derivatives previously reported. Electrochemical titrations of the two TTFAQ D/A triads with selected transition metal cations (Ag+ and Cu2+) were examined by cyclic

  合成了两个蒽醌型π扩展的四硫富瓦烯（TTFAQ）核心的D / A三单元组，并通过紫外可见吸收和循环伏安分析对其进行了表征。通过与先前报道的类似TTFAQ衍生物进行比较，揭示了电子取代基的作用。通过循环伏安法检测了两种带有选定过渡金属阳离子（Ag +和Cu 2+）的TTFAQ D / A三联体的电化学滴定，结果表明这种TTFAQ衍生物作为过渡金属离子的电化学传感器的潜在应用。
• C₆₀ Recognition from Extended Tetrathiafulvalene <i>Bis</i>-acetylide Platinum(II) Complexes
  作者：Guillaume Bastien、Paul I. Dron、Manon Vincent、David Canevet、Magali Allain、Sébastien Goeb、Marc Sallé

  DOI：10.1021/acs.orglett.6b02915

  日期：2016.11.18

  The favorable spatial organization imposed by the square planar 4,4′-di(tert-butyl)-2,2′-bipyridine (dbbpy) platinum(II) complex associated with the electronic and shape complementarity of π-extended tetrathiafulvalene derivatives (exTTF) toward fullerenes is usefully exploited to construct molecular tweezers, which display good affinities for C60.

  方形平面4,4'-二（叔丁基）-2,2'-联吡啶（dbbpy）铂（II）配合物与π延伸的四硫富瓦烯衍生物（exTTF）的电子和形状互补相关的良好空间组织）对富勒烯有效地用于构建分子镊子，该镊子显示出对C 60的良好亲和力。
• Phenylboronic acid-functionalized TTFAQ: modular synthesis and electrochemical recognition for saccharides
  作者：Min Shao、Yuming Zhao

  DOI：10.1016/j.tetlet.2010.02.171

  日期：2010.5

  A phenylboronic acid-functionalized pi-extended tetrathiafulvalene (TLFAQ) derivative was prepared through an efficient Cu-catalyzed alkyne-azide [3+2] cycloaddition reaction (click reaction). This boronic acid-TTFAQ hybrid system shows different electrochemical redox behavior upon titration with various saccharides in DMSO/H2O at pH 8.75, suggesting potential use in saccharide sensing and recognition. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and electronic properties of alkyne–TTFAQ based molecular wires
  作者：Guang Chen、Yuming Zhao

  DOI：10.1016/j.tetlet.2006.05.090

  日期：2006.7

  We herein describe the first synthesis of a series of pi-extend tetrathiafulvalene and alkyne based conjugated molecular wires. Electronic properties of these compounds were characterized by cyclic voltammetry, UV-vis absorption, and fluorescence spectroscopy. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and Electronic Properties of a Conjugated TTFAQ Trimer and Donor-Acceptor Ensembles of TTFAQ and Anthraquinone
  作者：Yuming Zhao、Min Shao、Guang Chen

  DOI：10.1055/s-2008-1032040

  日期：2008.2

  We report the first synthesis of a conjugated TTFAQ trimer as well as two TTFAQ-anthraquinone based donor-acceptor ensembles using Sonogashira and Horner-Wadsworth-Emmons reactions. Electronic absorption and electrochemical redox properties of these compounds are described.

  我们报告了利用 Sonogashira 反应和 Horner-Wadsworth-Emmons 反应首次合成的共轭 TTFAQ 三聚体以及两种基于 TTFAQ-蒽醌的供体-受体组合物。介绍了这些化合物的电子吸收和电化学氧化还原特性。