N-(4-hydroxyphenyl)-3,4-fulleropyrrolidine

• 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: N-(4-hydroxyphenyl)-3,4-fulleropyrrolidine
• 化学式: C₆₈H₉NO
• 分子量: 855.826
• InChiKey: OTFYSRNQBCROQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.7
• 重原子数：
  70
• 可旋转键数：
  1
• 环数：
  34.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-hydroxyphenyl)-3,4-fulleropyrrolidine 反应 0.08h， 以99%的产率得到足球烯
  参考文献：
  名称：

  Metal-free, retro-cycloaddition of fulleropyrrolidines in ionic liquids under microwave irradiation

  摘要：

  在微波辐照下，离子液体可在几分钟内将富勒吡咯烷定量环化为 [60] 富勒烯，而无需任何其他添加剂。

  DOI：

  10.1039/b906813a
• 作为产物：
  描述：

  聚合甲醛 、 N-(4-羟苯基)甘氨酸 、 足球烯 以 甲苯 为溶剂， 以33%的产率得到N-(4-hydroxyphenyl)-3,4-fulleropyrrolidine
  参考文献：
  名称：

  C60-蒽苯基乙炔杂化物的有序自组装和电子行为。

  摘要：

  DOI：

  10.1002/anie.200353001

文献信息

• 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.
• Ordered Self-Assembly and Electronic Behavior of C60–Anthrylphenylacetylene Hybrid
  作者：Seok Ho Kang、Hong Ma、Mun-Sik Kang、Kyoung-Soo Kim、Alex K.-Y. Jen、M. Hadi Zareie、Mehmet Sarikaya

  DOI：10.1002/anie.200353001

  日期：2004.3.12
• Metal-free, retro-cycloaddition of fulleropyrrolidines in ionic liquids under microwave irradiation
  作者：Ivan Guryanov、Alejandro Montellano López、Mauro Carraro、Tatiana Da Ros、Gianfranco Scorrano、Michele Maggini、Maurizio Prato、Marcella Bonchio

  DOI：10.1039/b906813a

  日期：——

  Quantitative cycloreversion of fulleropyrrolidines to [60]fullerene is achieved in ionic liquids within minutes under microwave irradiation without any further additives.

  在微波辐照下，离子液体可在几分钟内将富勒吡咯烷定量环化为 [60] 富勒烯，而无需任何其他添加剂。