4-(6-bromohexyloxymethyl)-9,10-bis[1,3]dithiol-2-ylidene-9,10-dihydroanthracene | 627099-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-(6-bromohexyloxymethyl)-9,10-bis[1,3]dithiol-2-ylidene-9,10-dihydroanthracene
• 英文别名: 2-[2-(6-Bromohexoxymethyl)-10-(1,3-dithiol-2-ylidene)anthracen-9-ylidene]-1,3-dithiole
• CAS: 627099-78-9
• 化学式: C₂₇H₂₅BrOS₄
• 分子量: 573.663
• InChiKey: RBELRTIGTBYRTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(6-bromohexyloxymethyl)-9,10-bis[1,3]dithiol-2-ylidene-9,10-dihydroanthracene 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 26.0h， 生成 di[6-(9,10-bis[1,3]dithiol-2-ylidene-9,10-dihydroanthracen-2-ylmethoxy)hexyl]disulfide
  参考文献：
  名称：

  Synthesis, Electrochemistry and Self-Assembled Monolayers of Novel Tetrathiafulvalene (TTF) and π-Extended TTF (exTTF) Disulfides

  摘要：

  The synthesis of a new series of tetrathiafalvalene (TTF) and pi-extended TTF (exTTF) disulfides and the electrochemical properties of self-assembled monolayers derived from these compounds are described. When the intermediate bromides 3 and 7 were reacted with thiourea, followed by basic hydrolysis, the expected thiol formation was not observed and only disulfides were obtained. A mechanism is proposed to explain the self-oxidation process of these compounds. For the first time SAMs of exTTF derivatives were prepared. Electrochemical data for SAMS of 6 and 8 reveal a single two-electron chemically reversible oxidation process to form a dicationic state, typical of the exTTF system. The SAMS are stable over extended periods of time and show electrochemical stability upon repeated potential scans.

  DOI：

  10.1021/jo034894s
• 作为产物：
  描述：

  1,6-二溴己烷 、 (9,10-di(1,3-dithiol-2-ylidene)-9,10-dihydroanthracen-2-yl)methanol 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 4-(6-bromohexyloxymethyl)-9,10-bis[1,3]dithiol-2-ylidene-9,10-dihydroanthracene
  参考文献：
  名称：

  Synthesis, Electrochemistry and Self-Assembled Monolayers of Novel Tetrathiafulvalene (TTF) and π-Extended TTF (exTTF) Disulfides

  摘要：

  The synthesis of a new series of tetrathiafalvalene (TTF) and pi-extended TTF (exTTF) disulfides and the electrochemical properties of self-assembled monolayers derived from these compounds are described. When the intermediate bromides 3 and 7 were reacted with thiourea, followed by basic hydrolysis, the expected thiol formation was not observed and only disulfides were obtained. A mechanism is proposed to explain the self-oxidation process of these compounds. For the first time SAMs of exTTF derivatives were prepared. Electrochemical data for SAMS of 6 and 8 reveal a single two-electron chemically reversible oxidation process to form a dicationic state, typical of the exTTF system. The SAMS are stable over extended periods of time and show electrochemical stability upon repeated potential scans.

  DOI：

  10.1021/jo034894s

文献信息

• Synthesis, Electrochemistry and Self-Assembled Monolayers of Novel Tetrathiafulvalene (TTF) and π-Extended TTF (<i>e</i><i>x</i>TTF) Disulfides
  作者：M. Ángeles Herranz、Lei Yu、Nazario Martín、Luis Echegoyen

  DOI：10.1021/jo034894s

  日期：2003.10.1

  The synthesis of a new series of tetrathiafalvalene (TTF) and pi-extended TTF (exTTF) disulfides and the electrochemical properties of self-assembled monolayers derived from these compounds are described. When the intermediate bromides 3 and 7 were reacted with thiourea, followed by basic hydrolysis, the expected thiol formation was not observed and only disulfides were obtained. A mechanism is proposed to explain the self-oxidation process of these compounds. For the first time SAMs of exTTF derivatives were prepared. Electrochemical data for SAMS of 6 and 8 reveal a single two-electron chemically reversible oxidation process to form a dicationic state, typical of the exTTF system. The SAMS are stable over extended periods of time and show electrochemical stability upon repeated potential scans.