4,5-ethylenedithio-4'-carboxytetrathiafulvalene | 166116-25-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: 4,5-ethylenedithio-4'-carboxytetrathiafulvalene
• 英文别名: 2-(5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-1,3-dithiole-4-carboxylic acid
• CAS: 166116-25-2
• 化学式: C₉H₆O₂S₆
• 分子量: 338.541
• InChiKey: YNUMZMMMJIWHLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4,5-ethylenedithio-4'-carboxytetrathiafulvalene 在 吡啶 、 草酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 4,5-ethylenedithio-4'-(N,N-dimethylcarbamoyl)tetrathiafulvalene
  参考文献：
  名称：

  The crystal chemistry of amide‐functionalized ethylenedithiotetrathiafulvalenes: EDT‐TTF‐CONRR′ (R, R′ = H, Me)

  摘要：

  本文描述了在TTF核心上直接官能化的乙烯基二硫代四硫富瓦烯（EDT-TTF）的制备，该官能团具有伯、仲或叔酰胺或酰肼官能团。本文报道了EDT-TTF-CO2H、EDT-TTF-CONH2、EDT-TTF-CONHMe和EDT-TTF-CONMe2的X射线晶体结构。这些官能化分子采用的固态结构似乎是氢键要求之间的折衷，氢键分别由OH、NH2、CH和CO基团提供和接受，而EDT-TTF部分的S·S·S范德华相互作用。TTF核心氢原子的活化，邻位于酰胺基，增强了其参与短C-H·O键的能力，从而产生在仲酰胺EDT-TTF-CONHMe中观察到的特征螯合R2R1(7)结构。

  DOI：

  10.1039/a902852h
• 作为产物：
  描述：

  Methyl 2-(5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-1,3-dithiole-4-carboxylate 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 15.0h， 以90%的产率得到4,5-ethylenedithio-4'-carboxytetrathiafulvalene
  参考文献：
  名称：

  The crystal chemistry of amide‐functionalized ethylenedithiotetrathiafulvalenes: EDT‐TTF‐CONRR′ (R, R′ = H, Me)

  摘要：

  本文描述了在TTF核心上直接官能化的乙烯基二硫代四硫富瓦烯（EDT-TTF）的制备，该官能团具有伯、仲或叔酰胺或酰肼官能团。本文报道了EDT-TTF-CO2H、EDT-TTF-CONH2、EDT-TTF-CONHMe和EDT-TTF-CONMe2的X射线晶体结构。这些官能化分子采用的固态结构似乎是氢键要求之间的折衷，氢键分别由OH、NH2、CH和CO基团提供和接受，而EDT-TTF部分的S·S·S范德华相互作用。TTF核心氢原子的活化，邻位于酰胺基，增强了其参与短C-H·O键的能力，从而产生在仲酰胺EDT-TTF-CONHMe中观察到的特征螯合R2R1(7)结构。

  DOI：

  10.1039/a902852h

文献信息

• Anion Responsive TTF-Appended Calix[4]arenes. Synthesis and Study of Two Different Conformers
  作者：Min Hee Lee、Qian-Yong Cao、Sung Kuk Kim、Jonathan L. Sessler、Jong Seung Kim

  DOI：10.1021/jo1021713

  日期：2011.2.4

  Two new cone- and 1,3-alternate-calix[4]arenes (cone-1 and 1,3-alt-1), bearing four modified TTF (tetrathiafulvalene) substituents on the upper rim, have been synthesized. The binding ability of these two sets of conformers for various anions, including F−, Cl−, Br−, I−, PF6−, ClO4−, HSO4−, CH3COO−, H2PO4−, and HP2O73−, was tested in organic media by monitoring the changes in their UV/vis and 1H NMR

  已经合成了两个新的锥形和1,3-交替杯 [4] 芳烃（锥形-1和1 , 3-alt -1），在上部边缘带有四个修饰的 TTF（四硫富瓦烯）取代基。这两组构象异构体对各种阴离子的结合能力，包括 F -、Cl -、Br -、I -、PF 6 -、ClO 4 -、HSO 4 -、CH 3 COO -、H 2 PO 4 -和惠普2 O7 3-在有机介质中通过监测其 UV/vis 和1 H NMR 光谱作为添加阴离子的函数的变化，以及通过循环伏安法 (CV)（所有阴离子作为其各自的 TBA 盐进行研究）进行测试。基于目前的研究结果，我们建议在基于杯[4]芳烃的整体识别框架中加入四个 TTF 单元会产生一个预先组织的受体系统，该系统显示出对焦磷酸盐 (HP 2 O 7 3− ) 阴离子的适度偏好.
• A tetrathiafulvalene–<scp>l</scp>-glutamine conjugated derivative as a supramolecular gelator for embedded C₆₀ and absorbed rhodamine B
  作者：Yucun Liu、Zhixue Liu、Yuan Wang、Lili Zhang、Xuemei Jiang、Guangbo Che

  DOI：10.1039/d0nj01816c

  日期：——

  weight gels made from tetrathiafulvalene derivatives have attracted great interest for various applications. In this work, a novel organic gelator derived from tetrathiafulvalene containing an L-glutamine moiety was designed and synthesized, and the electron-donating property and self-assembly behavior of the gelator were studied. It could form a charge-transfer complex with F4TCNQ in solution. And the

  由四硫富瓦烯衍生物制成的超分子低分子量凝胶引起了各种应用的极大兴趣。在这项工作中，设计并合成了一种新型的衍生自含有L-谷氨酰胺部分的四硫富瓦烯的有机胶凝剂，并研究了该胶凝剂的供电子性和自组装行为。它可以与溶液中的F 4 TCNQ形成电荷转移络合物。并且该胶凝剂在烷烃，芳族溶剂和CH 2 Cl 2中显示出良好的胶凝性能。通过场发射扫描电子显微镜和X射线衍射研究对形成的凝胶的形态和结构进行了表征，FT-IR结果11 H NMR和UV-Vis光谱表明，氢键和π-π相互作用在胶凝过程中起重要作用。此外，凝胶-溶胶转变可以通过化学氧化还原来调节，其中溶胶-凝胶转变的可逆性直接取决于糊化溶剂的性质。有趣的是，与C 60混合的胶凝剂可以在甲苯中形成电荷转移复合凝胶，当向胶凝剂中添加一当量的C 60时，观察到凝胶-溶胶转变温度逐渐升高。另外，由甲苯和n得到的凝胶己烷显示出能够从水中吸收有毒染料若丹明B的能
• Directing the Structures and Collective Electronic Properties of Organic Conductors: The Interplay of π-Overlap Interactions and Hydrogen Bonds
  作者：Karine Heuzé、Marc Fourmigué、Patrick Batail、Enric Canadell、Pascale Auban-Senzier

  DOI：10.1002/(sici)1521-3765(19991001)5:10<2971::aid-chem2971>3.0.co;2-s

  日期：——

  The ethylenedithiotetrathiafulvalene (EDT-TTF) directly functionalized with a primary amido group, which is both a hydrogen bond donor and acceptor group, is prepared from the corresponding ester. The electron-donating ability of EDT-TTF-CONH2 (1), which is comparable to that of bisethylenedithiotetrathiofulvalene (BEDT-TTF) despite the presence of the electron-withdrawing amidic group, allows the successful electrocrystallization of air-stable cation radical salts. Two completely different salts are obtained with the isosteric AsF6- and ReO4- ions; the former has 6:1 stoichiometry, and the latter has 2:1 stoichiometry. Compound (1)(6)(AsF6) crystallizes in the P (3) over bar space group, and the three crystallographically independent donor molecules are linked to each other through a combination of N-H ... O and C-H ... O hydrogen bonds. This strong trimeric motif organizes around the AsF6- ion located on the (3) over bar axis, exemplifying the templating effect of the octahedral anion on the whole structure. The presence of a uniform spin chain, as identified in the crystal structure, is confirmed by the Bonner-Fischer behavior of the magnetic susceptibility. In the 2:1 ReO4- salt, two crystallographically independent organic slabs are interconnected through N-H ... O(Re) hydrogen bonds, demonstrating the overlooked hydrogen-bond acceptor capability of this anion. The salt exhibits metallic behavior with a weak localization below 200 K. Both structures reveal the occurrence of a strong C-H ... O hydrogen bond involving the aromatic CH group of the EDT-TTF core, which is activated by the neighboring amidic moiety. Together with the NH ... O hydrogen bond, it gives rise to a cyclic motif noted R-2(1)(7) in Etter's graph set analysis.