5'-(11-oxoundecylthio)-4,4',5-tris(methylthio)tetrathiafulvalene | 224452-33-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5'-(11-oxoundecylthio)-4,4',5-tris(methylthio)tetrathiafulvalene
• 英文别名: 11-[[2-[4,5-bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-5-methylsulfanyl-1,3-dithiol-4-yl]sulfanyl]undecanal
• CAS: 224452-33-9
• 化学式: C₂₀H₃₀OS₈
• 分子量: 542.986
• InChiKey: GIJRMVFKFPJUAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  220
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  肌氨酸 、 足球烯 、 5'-(11-oxoundecylthio)-4,4',5-tris(methylthio)tetrathiafulvalene 以 甲苯 为溶剂， 反应 3.0h， 以25%的产率得到N-methyl-2-<10-<4,4',5-tris(methylthio)tetrathiafulvalen-5'-ylthio>decyl>-3,4-fulleropyrrolidine
  参考文献：
  名称：

  Long-lived photoproduced radical ions in tetrathiafulvalenes covalently tethered to C60

  摘要：

  C-60 or [60]fullerene, a reversible one- to six-electron acceptor with moderate first electron. affinity, was covalently linked, via a 1,3-dipolar addition reaction using azomethine ylides and two flexible insulating sigma-chains of different lengths, to a tetrathioalkyltetrathiafulvalene, a reversible one- to two-electron donor with low first ionization potential, yielding molecules 1 and 2. The electrochemical oxidation and reduction waves are the same as those of the separate components; UV-VIS spectra indicate no appreciable charge transfer in the ground state between the donor and acceptor moieties of these D-sigma-A systems 1 and 2: there is only a weak shoulder at 800 nm (epsilon approximate to 200 L mol(-1) cm(-1)), which could be the intervalence transfer band.These same molecules, as well as their donor and acceptor components taken separately, were electrochemically oxidized/reduced in liquid solutions, and also irradiated with laser light in low-temperature glasses. The electron paramagnetic resonance (EPR) spectra revealed photoexcited electron transfer at 77 K, with resulting S = 1/2 radical cation and radical anion states. In a glass at 77 K these radical signals survive a long time (up to several days) after the end of light irradiation. This may be separately solvated pairs of long-lived radicals D.+-sigma-A and D-sigma-A(.-) or, less likely, a long-lived excited-state zwitterionic biradical D.+-sigma-A(.-) with increasing temperature and the onset of diffusional motion, the EPR signals disappear.

  DOI：

  10.1039/a803737j
• 作为产物：
  描述：

  2-(10-bromodecyl)-1,3-dioxolane 在 盐酸 、 cesium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.5h， 生成 5'-(11-oxoundecylthio)-4,4',5-tris(methylthio)tetrathiafulvalene
  参考文献：
  名称：

  Long-lived photoproduced radical ions in tetrathiafulvalenes covalently tethered to C60

  摘要：

  C-60 or [60]fullerene, a reversible one- to six-electron acceptor with moderate first electron. affinity, was covalently linked, via a 1,3-dipolar addition reaction using azomethine ylides and two flexible insulating sigma-chains of different lengths, to a tetrathioalkyltetrathiafulvalene, a reversible one- to two-electron donor with low first ionization potential, yielding molecules 1 and 2. The electrochemical oxidation and reduction waves are the same as those of the separate components; UV-VIS spectra indicate no appreciable charge transfer in the ground state between the donor and acceptor moieties of these D-sigma-A systems 1 and 2: there is only a weak shoulder at 800 nm (epsilon approximate to 200 L mol(-1) cm(-1)), which could be the intervalence transfer band.These same molecules, as well as their donor and acceptor components taken separately, were electrochemically oxidized/reduced in liquid solutions, and also irradiated with laser light in low-temperature glasses. The electron paramagnetic resonance (EPR) spectra revealed photoexcited electron transfer at 77 K, with resulting S = 1/2 radical cation and radical anion states. In a glass at 77 K these radical signals survive a long time (up to several days) after the end of light irradiation. This may be separately solvated pairs of long-lived radicals D.+-sigma-A and D-sigma-A(.-) or, less likely, a long-lived excited-state zwitterionic biradical D.+-sigma-A(.-) with increasing temperature and the onset of diffusional motion, the EPR signals disappear.

  DOI：

  10.1039/a803737j

文献信息

• Long-lived photoproduced radical ions in tetrathiafulvalenes covalently tethered to C60
  作者：Klaus B. Simonsen、Valery V. Konovalov、Tatyana A. Konovalova、Tsuyoshi Kawai、Michael P. Cava、Lowell D. Kispert、Robert M. Metzger、Jan Becher

  DOI：10.1039/a803737j

  日期：——

  C-60 or [60]fullerene, a reversible one- to six-electron acceptor with moderate first electron. affinity, was covalently linked, via a 1,3-dipolar addition reaction using azomethine ylides and two flexible insulating sigma-chains of different lengths, to a tetrathioalkyltetrathiafulvalene, a reversible one- to two-electron donor with low first ionization potential, yielding molecules 1 and 2. The electrochemical oxidation and reduction waves are the same as those of the separate components; UV-VIS spectra indicate no appreciable charge transfer in the ground state between the donor and acceptor moieties of these D-sigma-A systems 1 and 2: there is only a weak shoulder at 800 nm (epsilon approximate to 200 L mol(-1) cm(-1)), which could be the intervalence transfer band.These same molecules, as well as their donor and acceptor components taken separately, were electrochemically oxidized/reduced in liquid solutions, and also irradiated with laser light in low-temperature glasses. The electron paramagnetic resonance (EPR) spectra revealed photoexcited electron transfer at 77 K, with resulting S = 1/2 radical cation and radical anion states. In a glass at 77 K these radical signals survive a long time (up to several days) after the end of light irradiation. This may be separately solvated pairs of long-lived radicals D.+-sigma-A and D-sigma-A(.-) or, less likely, a long-lived excited-state zwitterionic biradical D.+-sigma-A(.-) with increasing temperature and the onset of diffusional motion, the EPR signals disappear.