diindeno[1,2,3-bc:1',2',3'-ef]corannulene

• 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: diindeno[1,2,3-bc:1',2',3'-ef]corannulene
• 英文别名: diindeno[1,2,3-bc:1,2,3-ef]corannulene；Decacyclo[15.15.0.02,14.03,31.04,12.05,29.06,11.020,32.022,30.023,28]dotriaconta-1(17),2,4(12),5(29),6,8,10,13,15,18,20,22(30),23,25,27,31-hexadecaene
• 化学式: C₃₂H₁₄
• 分子量: 398.463
• InChiKey: QJGYHYPGUSEXRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  心环烯 、 2-氯苯基硼酸 在 一溴化碘 、 四(三苯基膦)钯 、 potassium carbonate 、 双(三环己基膦)二氯化钯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙醇 、 水 、 甲苯 、 异丁酰胺 为溶剂， 反应 30.75h， 以24 mg的产率得到diindeno[1,2,3-bc:1',2',3'-hi]corannulene
  参考文献：
  名称：

  Aromatic π-Systems More Curved Than C₆₀. The Complete Family of All Indenocorannulenes Synthesized by Iterative Microwave-Assisted Intramolecular Arylations

  摘要：

  Syntheses and X-ray crystal structures are reported for all seven members of the indenocorannulene family, comprising indenocorannulene, both isomers of diindenocorannulene, both isomers of triindenocorannulene, tetraindenocorannulene, and pentaindenocorannulene. With each additional indenoannulation, the pyramidalization of the trigonal carbon atoms at the hub of the corannulene increases. Five of the seven indenocorannulenes contain carbon atoms at the hub that are actually more pyramidalized than the carbon atoms of C-60. This work demonstrates, for the first time, that extended pi-systems with curvatures exceeding those of the most curved stable fullerenes and carbon nanotubes can be prepared by ordinary laboratory methods in solution, without recourse to high-temperature gas phase methods, such as flash vacuum pyrolysis. This proof of principle presages the days when scientists will be able to synthesize isomerically pure fullerenes and single-chirality nanotubes by well-understood, controlled chemical methods. Pentaindenocorannulene, itself, represents an attractive precursor to the C-5v end-cap of an all-carbon, single-walled, "armchair' [5,5]nanotube.

  DOI：

  10.1021/ja9031852

文献信息

• Reduction of Bowl-Shaped Hydrocarbons:  Dianions and Tetraanions of Annelated Corannulenes
  作者：Ivan Aprahamian、Dorin V. Preda、Mihail Bancu、Anthony P. Belanger、Tuvia Sheradsky、Lawrence T. Scott、Mordecai Rabinovitz

  DOI：10.1021/jo051949c

  日期：2006.1.1

  with lithium, the exception being systems that can stabilize the tetraanion with lithium by special means, such as aggregation or dimerization. One such system is cyclopenta[bc]corannulene (acecorannulylene), which gives a coordinative dimer that consists of two cyclopentacorannulene tetraanions, bound together in a convex−convex fashion by lithium cations. The points of contact in this dimer are two

  使用锂和钾金属还原了几种退火的邻苯二环戊二烯衍生物。研究发现，去核作用通过改变电荷分布而影响香兰素的环戊烯特性。与六元环退火的衍生物的二价阴离子比corannulene二价阴离子具有更少的年环特性和更少的顺性。这种作用在周围的Corannulenes中更加明显。-与五元环退火。还原过程中使用的碱金属对结果有很大影响，特别是对还原度有很大影响。大多数衍生物仅通过钾而不是锂被还原为四阴离子，例外的是可以通过特殊方式（例如聚集或二聚）稳定四价阴离子的体系。一个这样的系统是环戊四烯[ bc ] corannulene（acecorannulylene），它给出一个配位二聚体，该二聚体由两个环戊四烯环戊四阴离子通过锂阳离子以凸-凸的方式结合在一起。在该二聚体中的接触点是来自每个环戊四烯环烯单元的两个再杂化的碳，它们被两个锂阳离子桥接在一起。
• Aromatic π-Systems More Curved Than C₆₀. The Complete Family of All Indenocorannulenes Synthesized by Iterative Microwave-Assisted Intramolecular Arylations
  作者：Brian D. Steinberg、Edward A. Jackson、Alexander S. Filatov、Atsushi Wakamiya、Marina A. Petrukhina、Lawrence T. Scott

  DOI：10.1021/ja9031852

  日期：2009.8.5

  Syntheses and X-ray crystal structures are reported for all seven members of the indenocorannulene family, comprising indenocorannulene, both isomers of diindenocorannulene, both isomers of triindenocorannulene, tetraindenocorannulene, and pentaindenocorannulene. With each additional indenoannulation, the pyramidalization of the trigonal carbon atoms at the hub of the corannulene increases. Five of the seven indenocorannulenes contain carbon atoms at the hub that are actually more pyramidalized than the carbon atoms of C-60. This work demonstrates, for the first time, that extended pi-systems with curvatures exceeding those of the most curved stable fullerenes and carbon nanotubes can be prepared by ordinary laboratory methods in solution, without recourse to high-temperature gas phase methods, such as flash vacuum pyrolysis. This proof of principle presages the days when scientists will be able to synthesize isomerically pure fullerenes and single-chirality nanotubes by well-understood, controlled chemical methods. Pentaindenocorannulene, itself, represents an attractive precursor to the C-5v end-cap of an all-carbon, single-walled, "armchair' [5,5]nanotube.