1,4-bis(fullero[c]pyrrolidin-1-yl)benzene | 1070903-05-7

• 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: 1,4-bis(fullero[c]pyrrolidin-1-yl)benzene
• 英文别名: BDC60
• CAS: 1070903-05-7
• 化学式: C₁₃₀H₁₂N₂
• 分子量: 1601.54
• InChiKey: XEQQBAWKYNVMHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  30.2
• 重原子数：
  132
• 可旋转键数：
  2
• 环数：
  67.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 N,N'-1,4-亚苯基二甘氨酸 、 足球烯 以 邻二氯苯 为溶剂， 反应 6.17h， 以28%的产率得到1,4-bis(fullero[c]pyrrolidin-1-yl)benzene
  参考文献：
  名称：

  Fullerene-Based Anchoring Groups for Molecular Electronics

  摘要：

  We present results on a new fullerne-based anchoring group for molecular electronics. Using lithographic mechanically controllable break junctions in vaccum we have determined the conductance and stability of single-molecule junctions of 1,4-bis(fullero[c]pyrrolidin-1-yl)benzene. The compound can be self-assembled from solution and has a low-bias conductance of 3 x 10(-4) G(0). Compared to 1,4-benzenedithiol the fullerene-anchored molecule exhibits a considerably lower conductance spread. In addition, the signature of the new compound in histograms is more significant than that of 1,4-benzenediamine, probably owing to a more stable adsorption motif. Statistical analyses of the breaking of the junctions confirm the stability of the fullerene-gold bond.

  DOI：

  10.1021/ja804699a

文献信息

• Fullerene-Based Anchoring Groups for Molecular Electronics
  作者：Christian A. Martin、Dapeng Ding、Jakob Kryger Sørensen、Thomas Bjørnholm、Jan M. van Ruitenbeek、Herre S. J. van der Zant

  DOI：10.1021/ja804699a

  日期：2008.10.8

  We present results on a new fullerne-based anchoring group for molecular electronics. Using lithographic mechanically controllable break junctions in vaccum we have determined the conductance and stability of single-molecule junctions of 1,4-bis(fullero[c]pyrrolidin-1-yl)benzene. The compound can be self-assembled from solution and has a low-bias conductance of 3 x 10(-4) G(0). Compared to 1,4-benzenedithiol the fullerene-anchored molecule exhibits a considerably lower conductance spread. In addition, the signature of the new compound in histograms is more significant than that of 1,4-benzenediamine, probably owing to a more stable adsorption motif. Statistical analyses of the breaking of the junctions confirm the stability of the fullerene-gold bond.
• Fulleropyrrolidine End-Capped Molecular Wires for Molecular Electronics—Synthesis, Spectroscopic, Electrochemical, and Theoretical Characterization
  作者：Jakob Kryger Sørensen、Jeppe Fock、Anders Holmen Pedersen、Asger B. Petersen、Karsten Jennum、Klaus Bechgaard、Kristine Kilså、Victor Geskin、Jérôme Cornil、Thomas Bjørnholm、Mogens Brøndsted Nielsen

  DOI：10.1021/jo102066x

  日期：2011.1.7

  In continuation of previous studies showing promising metal molecule contact properties a variety of C-60 end-capped "molecular wires" for molecular electronics were prepared by variants of the Prato 1,3-dipolar cycloaddition reaction. Either benzene or fluorene was chosen as the central wire, and synthetic protocols for derivatives terminated with one or two fullero[c]pyrrolidine "electrode anchoring" groups were developed. An aryl-substituted aziridine could in some cases be employed directly as the azomethine ylide precursor for the Prato reaction without the need of having an electron-withdrawing ester group present. The effect of extending the pi-system of the central wire from 1,4-phenylenediamine to 2,7-fluorenediamine was investigated by absorption, fluorescence, and electrochemical methods. The central wire and the Co-60 end-groups were found not to electronically communicate in the ground state. However, the fluorescence of C60 was quenched by charge transfer from the wire to C-60. Quantum chemical calculations predict and explain the collapse of coherent electronic transmission through one of the fulleropyrrolidine-terminated molecular wires.