(2,3)-(6,7)-bis(1,4-naphthoquinone)tetrathiafulvalene | 65160-05-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2,3)-(6,7)-bis(1,4-naphthoquinone)tetrathiafulvalene
• 英文别名: bis(1,4-naphthoquinone)tetrathiafulvalene；2-(4,9-Dioxobenzo[f][1,3]benzodithiol-2-ylidene)benzo[f][1,3]benzodithiole-4,9-dione
• CAS: 65160-05-6
• 化学式: C₂₂H₈O₄S₄
• 分子量: 464.567
• InChiKey: QNXFVOXZDSTAEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  benzocyclohexa-2,5-diene-1,4-dione-1,3-thiole-2-one 在 sodium hypochlorite 、 sodium dithionite 、 亚磷酸三乙酯 作用下， 以 乙醇 、 苯 为溶剂， 反应 0.5h， 生成 (2,3)-(6,7)-bis(1,4-naphthoquinone)tetrathiafulvalene
  参考文献：
  名称：

  Tetrathiafulvalene quinones, hydroquinones and esters

  摘要：

  Benzocyclohexa-2,5-diene-1,4-dione-1,3-thiole-2-thione (2) was synthesized starting with 2,3-dichloronapthoquinone (1). Compounds 3 and 4 were also obtained; however, the yield of 2 can be increased through control of the temperature and reaction time. Reaction of 2 with triethylphosphite gave 5 and the tetrathiafulvalene ester 6. The tetrathiafulvalenequinone (9) was obtained by hydrolysis of 6 followed by oxidation of & Compound 9 was obtained more directly by hydrogenation of 2 followed by coupling with triethylphosphite and oxidation. Chloranil was used to prepare the dithiafulvene quinone 12 which was reduced, coupled with triethylphosphite to form, presumably, polymer 13. The reactions were repeated using the hexanoic acid esters of the corresponding hydroquinone thiafulvalenes. The crystal structures of 2, 3, 4, 5, 6a and 10 were determined by X-ray diffraction. Cyclic voltammetry studies show the tetrathiafulvalene quinones reduce like quinones, but do not exhibit the oxidation properties of tetrathiafulvalenes.

  DOI：

  10.1016/s0040-4020(01)89885-9

文献信息

• Novel Fused D−A Dyad and A−D−A Triad Incorporating Tetrathiafulvalene and <i>p</i>-Benzoquinone
  作者：Frédéric Dumur、Nicolas Gautier、Nuria Gallego-Planas、Yücel Şahin、Eric Levillain、Nicolas Mercier、Piétrick Hudhomme、Matteo Masino、Alberto Girlando、Vega Lloveras、José Vidal-Gancedo、Jaume Veciana、Concepció Rovira

  DOI：10.1021/jo035689f

  日期：2004.3.1

  compounds of the cation radical and anion radical obtained upon (electro)chemical oxidation and reduction, respectively, was monitored by optical and ESR spectroscopies. The anion radical Q−TTF−Q-• triad was demonstrated to be a class II mixed-valence system with the existence of a temperature-dependent intramolecular electron transfer. The crystallographic tendency of these fused systems to overlap in

  新型融合的供体-受体二元体（TTF-Q或D-A）和受体-供体-受体三联体（Q-TTF-Q或A-D-A）结合了供体四硫富瓦烯（TTF）和受体对苯并醌（Q ）已合成。这些分子的溶液紫外可见光谱显示出低能量吸收带，这归因于两个拮抗单元之间的分子内电荷转移。通过循环伏安法显示了供体和受体部分可逆的氧化和还原波的存在，与TTF /醌单元的比例一致。通过光学和ESR光谱法监测由这些化合物分别在（电）化学氧化和还原时获得的阳离子自由基和阴离子自由基的连续生成。该阴离子自由基Q-TTF-Q - •三单元组被证明是具有温度依赖性分子内电子转移的II类混合价体系。还讨论了这些熔融系统在交替的A-D-A单元的混合堆栈中重叠的晶体学趋势。
• DEMETRIADIS N. G.; HUANG S. J.; SAMULSKI E. T., TETRAHEDRON LETT. <TELE-AY>, 1977, NO 26, 2223-2226
  作者：DEMETRIADIS N. G.、 HUANG S. J.、 SAMULSKI E. T.

  DOI：——

  日期：——
• Tetrathiafulvalene quinones, hydroquinones and esters
  作者：William H Watson、Etim E Eduok、Ram P Kashyap、Mariusz Krawiec

  DOI：10.1016/s0040-4020(01)89885-9

  日期：1993.4

  Benzocyclohexa-2,5-diene-1,4-dione-1,3-thiole-2-thione (2) was synthesized starting with 2,3-dichloronapthoquinone (1). Compounds 3 and 4 were also obtained; however, the yield of 2 can be increased through control of the temperature and reaction time. Reaction of 2 with triethylphosphite gave 5 and the tetrathiafulvalene ester 6. The tetrathiafulvalenequinone (9) was obtained by hydrolysis of 6 followed by oxidation of & Compound 9 was obtained more directly by hydrogenation of 2 followed by coupling with triethylphosphite and oxidation. Chloranil was used to prepare the dithiafulvene quinone 12 which was reduced, coupled with triethylphosphite to form, presumably, polymer 13. The reactions were repeated using the hexanoic acid esters of the corresponding hydroquinone thiafulvalenes. The crystal structures of 2, 3, 4, 5, 6a and 10 were determined by X-ray diffraction. Cyclic voltammetry studies show the tetrathiafulvalene quinones reduce like quinones, but do not exhibit the oxidation properties of tetrathiafulvalenes.