trimethyl-[2-[4-[2-[4-[2-(9-methyl(C60-Ih)[5,6]fulleren-1-yl)ethynyl]-2-nitrophenyl]ethynyl]phenyl]sulfanylethyl]silane | 1187448-86-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: trimethyl-[2-[4-[2-[4-[2-(9-methyl(C60-Ih)[5,6]fulleren-1-yl)ethynyl]-2-nitrophenyl]ethynyl]phenyl]sulfanylethyl]silane
• CAS: 1187448-86-7
• 化学式: C₈₂H₂₃NO₂SSi
• 分子量: 1114.24
• InChiKey: DVTSFWWBHUSLGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.1
• 重原子数：
  87
• 可旋转键数：
  8
• 环数：
  34.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-[4-[2-(4-Ethynyl-2-nitrophenyl)ethynyl]phenyl]sulfanylethyl-trimethylsilane 、 足球烯 、 碘甲烷 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以23%的产率得到trimethyl-[2-[4-[2-[4-[2-(9-methyl(C60-Ih)[5,6]fulleren-1-yl)ethynyl]-2-nitrophenyl]ethynyl]phenyl]sulfanylethyl]silane
  参考文献：
  名称：

  Fullerene/Thiol-Terminated Molecules

  摘要：

  A series of fullerene-terminated oligo(phenylene ethynylene) (OPEs) have been synthesized for potential use in electronic or optoelectronic device monolayers. Electronic properties such as the energy levels and the distribution of HOMOs and LUMOs of fullerene-terminated OPEs have been calculated using the ab initio method at the B3LYP/6-31G(d) level. The calculations have revealed the concentration of frontier orbitals on the fullerene cage and a narrow distribution of HOMO-LUMO energy gaps. Ultraviolet photoelectron spectroscopy and inverse photoemission spectroscopy studies have been performed to further examine the electronic properties of the fullerene-terminated OPEs on gold surfaces. The obtained broad photoelectron spectra Suggest that there are strong intermolecular interactions in the fullerene self-assembled monolayers, and the small bandgap (similar to 1.5 eV), determined by the photoelectron spectroscopy, indicates the unique nature of the fullerene-terminated OPEs in which the C-60 moiety can be connected to the Au surface through the conjugated OPE backbone.

  DOI：

  10.1021/jo901701j

文献信息

• Fullerene/Thiol-Terminated Molecules
  作者：Yasuhiro Shirai、Jason M. Guerrero、Takashi Sasaki、Tao He、Huanjun Ding、Guillaume Vives、Byung-Chan Yu、Long Cheng、Austen K. Flatt、Priscilla G. Taylor、Yongli Gao、James M. Tour

  DOI：10.1021/jo901701j

  日期：2009.10.16

  A series of fullerene-terminated oligo(phenylene ethynylene) (OPEs) have been synthesized for potential use in electronic or optoelectronic device monolayers. Electronic properties such as the energy levels and the distribution of HOMOs and LUMOs of fullerene-terminated OPEs have been calculated using the ab initio method at the B3LYP/6-31G(d) level. The calculations have revealed the concentration of frontier orbitals on the fullerene cage and a narrow distribution of HOMO-LUMO energy gaps. Ultraviolet photoelectron spectroscopy and inverse photoemission spectroscopy studies have been performed to further examine the electronic properties of the fullerene-terminated OPEs on gold surfaces. The obtained broad photoelectron spectra Suggest that there are strong intermolecular interactions in the fullerene self-assembled monolayers, and the small bandgap (similar to 1.5 eV), determined by the photoelectron spectroscopy, indicates the unique nature of the fullerene-terminated OPEs in which the C-60 moiety can be connected to the Au surface through the conjugated OPE backbone.