2-[2-[4,5-Bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-1,2-bis(4-ethynylphenyl)ethylidene]-4,5-bis(methylsulfanyl)-1,3-dithiole | 1370001-39-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-[2-[4,5-Bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-1,2-bis(4-ethynylphenyl)ethylidene]-4,5-bis(methylsulfanyl)-1,3-dithiole
• 英文别名: 2-[2-[4,5-bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-1,2-bis(4-ethynylphenyl)ethylidene]-4,5-bis(methylsulfanyl)-1,3-dithiole
• CAS: 1370001-39-0
• 化学式: C₂₈H₂₂S₈
• 分子量: 615.011
• InChiKey: LDRJFZGVLKDTOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• 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-[2-[4,5-Bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-1,2-bis(4-ethynylphenyl)ethylidene]-4,5-bis(methylsulfanyl)-1,3-dithiole 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 3.08h， 生成 [2-[[4-[4-[1,2-Bis[4,5-bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-2-[4-[1-[(2-boronophenyl)methyl]triazol-4-yl]phenyl]ethyl]phenyl]triazol-1-yl]methyl]phenyl]boronic acid
  参考文献：
  名称：

  TTFV molecular tweezers with phenylboronic acid and phenylboronate endgroups: modular synthesis and electrochemical responses to saccharides and fluoride ion

  摘要：

  Tweezer-like molecular systems containing a redox-active tetrathiafulvalene vinylogue (TTFV) unit and two phenylboronate or phenylboronic acid endgroups were synthesized via the Cu-catalyzed alkyne azide coupling (i.e., click) reaction. The TTFV-phenylboronic acid derivative was found to show different differential pulse voltammetric (DPV) responses to various monosaccharides in aqueous DMSO at pH 7.41, suggesting potential use in electrochemical sensing of saccharides. Moreover, the TTFV-phenylboronate derivative exhibited strong binding to the fluoride ion, giving rise to sensitive electrochemical detection of the fluoride ion. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.11.036
• 作为产物：
  描述：

  4-三甲基硅乙炔基苯甲醛 在 碘 、 potassium carbonate 、 三甲氧基磷 作用下， 以 四氢呋喃 、 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 2-[2-[4,5-Bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-1,2-bis(4-ethynylphenyl)ethylidene]-4,5-bis(methylsulfanyl)-1,3-dithiole
  参考文献：
  名称：

  Reversible dispersion and releasing of single-walled carbon nanotubes by a stimuli-responsive TTFV-phenylacetylene polymer

  摘要：

  合成了TTFV-苯乙炔折叠聚合物，该聚合物在氧化还原或pH刺激的控制下表现出在有机溶剂中可逆分散和释放单壁碳纳米管的性能。

  DOI：

  10.1039/c2cc17935k

文献信息

• Click synthesized dianthryl–TTFV: an efficient fluorescent turn-on probe for transition metal ions
  作者：Karimulla Mulla、Prateek Dongare、David W. Thompson、Yuming Zhao

  DOI：10.1039/c2ob06828a

  日期：——

  Tetrathiafulvalene vinylogue (TTFV) was functionalized with two anthryl fluorophores via Cu(I)-catalyzed alkyne–azide [3 + 2] cycloaddition, forming a dianthryl–TTFV hybrid to show fluorescent turn-on sensing behaviour for Cu2+, Fe2+, and Cd2+ ions in THF with remarkably low detection limit down to the sub-ppm level.

  四硫富瓦烯乙烯（TTFV）通过Cu（I）催化炔-叠氮[3 + 2]环加成与两个蒽基荧光团发生官能团化反应，形成二蒽基-TTFV杂化物，用于显示THF中Cu2+、Fe2+和Cd2+离子的荧光开启传感行为，检测限极低，可达亚ppm级。
• Synthesis and properties of TTFV-hinged molecular tweezers
  作者：Guang Chen、Stephen Bouzan、Yuming Zhao

  DOI：10.1016/j.tetlet.2010.10.032

  日期：2010.12

  Two molecular tweezers containing a tetrathiafulvalene vinylogue (TTFV) core were synthesized via sequential Sonogashira and Horner-Wadsworth-Emmons (HWE) reactions. The electrochemical and spectroscopic properties of these TTFV tweezers were investigated by UV-vis absorption spectroscopy, cyclic voltammetry, and spectro-electrochemical measurements. The property characterizations suggest potential application in electrochemically-actuated molecular switching devices. (C) 2010 Elsevier Ltd. All rights reserved.
• Acetylenic Phenyldithiafulvene: A Versatile Synthon for TTFV-Based Macromolecules
  作者：Guang Chen、Ilias Mahmud、Louise N. Dawe、Yuming Zhao

  DOI：10.1021/ol9026683

  日期：2010.2.19

  An acetylenic phenyldithiafulvene was developed as a versatile synthon for diverse TTFV-based macromolecular scaffolds. Through different coupling reaction sequences, shape-persistent macrocycles and linear TTFV-embedded polymers have been obtained and thereafter characterized by spectroscopic and voltammetric analyses. The TTFV polymer thin films generated via electropolymerization of a dithiafulvenyl-end-capped diyne monomer showed promising prospects in electrochromic and redox switchable molecular devices.
• Reversible dispersion and releasing of single-walled carbon nanotubes by a stimuli-responsive TTFV-phenylacetylene polymer
  作者：Shuai Liang、Guang Chen、Jessica Peddle、Yuming Zhao

  DOI：10.1039/c2cc17935k

  日期：——

  A TTFV-phenylacetylene folding polymer was synthesized to exhibit the property of reversibly dispersing and releasing single-walled carbon nanotubes in organic solvents under the control of redox or pH stimuli.

  合成了TTFV-苯乙炔折叠聚合物，该聚合物在氧化还原或pH刺激的控制下表现出在有机溶剂中可逆分散和释放单壁碳纳米管的性能。
• TTFV molecular tweezers with phenylboronic acid and phenylboronate endgroups: modular synthesis and electrochemical responses to saccharides and fluoride ion
  作者：Karimulla Mulla、Yuming Zhao

  DOI：10.1016/j.tetlet.2013.11.036

  日期：2014.1

  Tweezer-like molecular systems containing a redox-active tetrathiafulvalene vinylogue (TTFV) unit and two phenylboronate or phenylboronic acid endgroups were synthesized via the Cu-catalyzed alkyne azide coupling (i.e., click) reaction. The TTFV-phenylboronic acid derivative was found to show different differential pulse voltammetric (DPV) responses to various monosaccharides in aqueous DMSO at pH 7.41, suggesting potential use in electrochemical sensing of saccharides. Moreover, the TTFV-phenylboronate derivative exhibited strong binding to the fluoride ion, giving rise to sensitive electrochemical detection of the fluoride ion. (C) 2013 Elsevier Ltd. All rights reserved.