10-(5,6-Dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)anthracen-9-one | 220115-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 10-(5,6-Dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)anthracen-9-one
• CAS: 220115-99-1
• 化学式: C₁₉H₁₂OS₄
• 分子量: 384.568
• InChiKey: MIFDRLUBWCQMDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  丙二腈 、 10-(5,6-Dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)anthracen-9-one 在 吡啶 、 四氯化钛 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 20.0h， 以54%的产率得到2-[10-(5,6-Dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)anthracen-9-ylidene]propanedinitrile
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1002/(sici)1521-3765(19981204)4:12<2580::aid-chem2580>3.3.co;2-#
• 作为产物：
  描述：

  蒽酮 、 2-(methylthio)-5,6-dihydro-1,3-dithiolo<4,5-b><1,4>dithiin-2-ium tetrafluoroborate 在 吡啶 、 溶剂黄146 作用下， 以69%的产率得到10-(5,6-Dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)anthracen-9-one
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

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