bis[4,5-di(methylsulfanyl)-1,3-dithiol-2-ylidene]-9,10-dihydroanthracene | 159638-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: bis[4,5-di(methylsulfanyl)-1,3-dithiol-2-ylidene]-9,10-dihydroanthracene
• 英文别名: TTM-exTTF；tetramethylthio-exTTF；2-[10-[4,5-Bis(methylsulfanyl)-1,3-dithiol-2-ylidene]anthracen-9-ylidene]-4,5-bis(methylsulfanyl)-1,3-dithiole
• CAS: 159638-86-5
• 化学式: C₂₄H₂₀S₈
• 分子量: 564.951
• InChiKey: CIUCNTALRIOHCX-UHFFFAOYSA-N

物化性质

• 沸点：
  642.4±55.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  bis[4,5-di(methylsulfanyl)-1,3-dithiol-2-ylidene]-9,10-dihydroanthracene 在 air 作用下， 以 氯仿 为溶剂， 生成 10-[4,5-bis(methylthio)-1,3-dithiol-2-ylidene]anthracene-9(10H)-one
  参考文献：
  名称：

  π扩展的9,10-双（1,3-二硫醇-2-亚烷基）-9,10-二氢蒽系统的光化学：自由基阳离子，阳离子和衍生产物的生成和表征。

  摘要：

  指示中的平面蒽和1,3-二硫鎓环形成77.2度的二面角；这种构型与先前报道的中性1的鞍形结构显着不同。

  DOI：

  10.1002/1521-3765(20010302)7:5<973::aid-chem973>3.0.co;2-#
• 作为产物：
  描述：

  蒽醌 、 dimethyl 4,5-bis(methylthio)-1,3-dithiole phosphonate ester 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以100%的产率得到bis[4,5-di(methylsulfanyl)-1,3-dithiol-2-ylidene]-9,10-dihydroanthracene
  参考文献：
  名称：

  Synthesis and Properties of Tetrathiafulvalene Derivatives Containing Quinoid Structures: Novel Electron Donors of Organic Conductors

  摘要：

  Wittig-Horner reactions of 2-dimethoxyphosphinyl-1,3-dithiole derivatives with a benzoquinone-cyclopentadiene adduct and anthraquinone afforded new types of electron donors with alkylthio groups for organic conductors which showed reversible oxidation waves on cyclic voltammetries and formed conductive charge-transfer complexes with TCNQ or DDQ.

  DOI：

  10.3987/com-94-6802

文献信息

• Donor–π-Acceptor Species Derived from Functionalised 1,3-Dithiol-2-ylidene Anthracene Donor Units Exhibiting Photoinduced Electron Transfer Properties: Spectroscopic, Electrochemical, X-Ray Crystallographic and Theoretical Studies
  作者：Andrei S. Batsanov、Martin R. Bryce、Malcolm A. Coffin、Andrew Green、Ronald E. Hester、Judith A. K. Howard、Igor K. Lednev、Nazario Martín、Adrian J. Moore、John N. Moore、Enrique Ortí、Luis Sánchez、María Savirón、Pedro M. Viruela、Rafael Viruela、Tian-Qing Ye

  DOI：10.1002/(sici)1521-3765(19981204)4:12<2580::aid-chem2580>3.3.co;2-#

  日期：1998.12.4

  Novel single-component donor- acceptor species 7 and 8 have been synthesised from substituted 10-(1,3-dithiol-2-ylidene)anthracen-9(10H)one 6 by reaction with Lehnert's reagent and with N,N'-bis(trimethylsilyl)carbodiimide, respectively. The steady-state UV/visible spectra of these systems contain a solvatochromic band arising from intramolecular charge transfer between the donor and acceptor groups Ultrafast time-resolved spectroscopy shows that the excited state formed on photolysis has a lifetime of 170-400 ps, which depends strongly on solvent polarity. Cyclic voltammetric data indicate the presence of two active redox centres in the molecules: electrochemical oxidation and reduction form cation radicals and anion radicals, respectively. The X-ray crystal structures of compounds 6a, 7b and 11a reveal that all three molecules are severely distorted from planarity, with the central ring of the anthracenediylidene moiety adopting a boat conformation. The molecular structures of 6, 7 and 11 have been investigated theoretically at the ab initio 6-31G* level. Calculated geometries are in good agreement with the X-ray data and clearly show the decrease in steric hindrance along the series 11>7>8>6. The calculations support the intramolecular charge-transfer nature of the lowest energy absorption band observed for 6, 7 and 8, and explain the origin of the redox properties for these compounds. The optimised geometries of the cation radical, anion radical and dianion of compound 7 illustrate the structural changes induced by the charging process. For the dianion, the steric interactions are alleviated by rotation of the acceptor dicyanomethylene unit, but the presence of the donor dithiole group hinders the achievement of a fully aromatic planar structure for the central anthracene skeleton.
• Saito Katsuhiro, Sugiura Chikayuki, Tanimoto Emi, Saito Katsushi, Yamashi+, Heterocycles, 38 (1994) N 10, S 2153-2158
  作者：Saito Katsuhiro, Sugiura Chikayuki, Tanimoto Emi, Saito Katsushi, Yamashi+

  DOI：——

  日期：——