1,3,5,7,9-pentakis(o-chlorophenyl)corannulene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,3,5,7,9-pentakis(o-chlorophenyl)corannulene
• 英文别名: 1,3,5,7,9-pentakis(2-chlorophenyl)corannulene；2,5,8,11,20-Pentakis(2-chlorophenyl)hexacyclo[11.5.2.04,17.07,16.010,15.014,18]icosa-1(19),2,4(17),5,7,9,11,13(20),14(18),15-decaene；2,5,8,11,20-pentakis(2-chlorophenyl)hexacyclo[11.5.2.04,17.07,16.010,15.014,18]icosa-1(19),2,4(17),5,7,9,11,13(20),14(18),15-decaene
• 化学式: C₅₀H₂₅Cl₅
• 分子量: 803.013
• InChiKey: DSEPTOWZRFIPDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.5
• 重原子数：
  55
• 可旋转键数：
  5
• 环数：
  11.0
• 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

• 作为反应物：
  描述：

  1,3,5,7,9-pentakis(o-chlorophenyl)corannulene 在 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 N,N-二甲基乙酰胺 为溶剂， 200.0 ℃ 、1.5 MPa 条件下， 反应 0.25h， 以19%的产率得到pentaindenocorannulene
  参考文献：
  名称：

  Pentaindenocorannulene：特性，装配体和C60配合物

  摘要：

  Pentaindenocorannulene（C 50 ħ 20  ，1），深碗多核芳烃，接受4个电子，在柱状碗在碗组件和形成嵌套ç结晶60 @ 1 2复合物。介绍了光谱，结构和计算。

  DOI：

  10.1002/anie.201608337
• 作为产物：
  描述：

  2-溴氯苯 、 1,3,5,7,9-pentakis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)corannulene 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以70%的产率得到1,3,5,7,9-pentakis(o-chlorophenyl)corannulene
  参考文献：
  名称：

  Pentaindenocorannulene：特性，装配体和C60配合物

  摘要：

  Pentaindenocorannulene（C 50 ħ 20  ，1），深碗多核芳烃，接受4个电子，在柱状碗在碗组件和形成嵌套ç结晶60 @ 1 2复合物。介绍了光谱，结构和计算。

  DOI：

  10.1002/anie.201608337

文献信息

• [EN] NANOSTRUCTURES AND METHODS FOR CHEMICALLY SYNTHESIZING NANOSTRUCTURES<br/>[FR] NANOSTRUCTURES ET PROCÉDÉS DE SYNTHÈSE CHIMIQUE DE NANOSTRUCTURES
  申请人：TRUSTEES BOSTON COLLEGE

  公开号：WO2010151307A1

  公开（公告）日：2010-12-29

  The present invention generally relates to nanostructure compositions, as well as methods for the controlled synthesis of nanostructures, such as carbon nanotubes. In some embodiments, methods involving iterative growth of a nanostructure template to homogeneously produce nanostructure compositions are provided. The compositions may include nanostructures having a specific length, width, diameter, ring orientation, and/or other characteristics. Using methods described herein, nanostructures (e.g., nanotubes) having uniform properties, such as electrical conductivity, may be readily produced. The ability to provide homogeneous nanostructure compositions may be advantageous in the design and fabrication of numerous materials and electronic devices.

  本发明一般涉及纳米结构组合物，以及用于控制合成纳米结构的方法，例如碳纳米管。在某些实施例中，提供了涉及通过迭代生长纳米结构模板以均匀产生纳米结构组合物的方法。这些组合物可以包括具有特定长度、宽度、直径、环向取向和/或其他特征的纳米结构。使用本文描述的方法，可以轻松生产具有均匀性能的纳米结构（例如纳米管），如电导率。提供均匀的纳米结构组合物的能力在设计和制造许多材料和电子器件方面可能是有利的。
• Pentaindenocorannulene and Tetraindenocorannulene:  New Aromatic Hydrocarbon π Systems with Curvatures Surpassing That of C₆₀
  作者：Edward A. Jackson、Brian D. Steinberg、Mihail Bancu、Atsushi Wakamiya、Lawrence T. Scott

  DOI：10.1021/ja067487h

  日期：2007.1.1

  Short syntheses and X-ray crystal structures are reported for two new geodesic polyarenes, pentaindenocorannulene (1, C50H20) and tetraindenocorannulene (2, C44H18). These extended aromatic systems constitute the largest curved subunits of C-60 ever prepared. In agreement with theoretical predictions, the trigonal carbon atoms at the cores of these new hydrocarbons suffer even greater pyramidalization than that exhibited by the carbon atoms of C-60 (average POAV angles = 12.6, 12.1, and 11.6 degrees for 1, 2, and C-60, respectively). These syntheses of such highly curved systems by solution phase methods, starting from compounds that were derived from planar starting materials also by solution phase methods, demonstrate unequivocally that rational chemical syntheses of fullerenes, carbon nanotubes, and related carbon-rich molecules should all be possible using exclusively solution chemical methods! Recourse to high-temperature gas-phase pyrolysis should not be necessary. The synthesis of 1 begins with a 5-fold Suzuki-Miyaura coupling of 1,3,5,7,9-pentachlorocorannulene with 2-chlorophenylboronic acid, giving 1,3,5,7,9-pentakis(2-chlorophenyl)corannulene in 48% isolated yield (86% average yield per C-C coupling). Subsequent conversion to pentaindenocorannulene (1) was achieved in 35% isolated yield (81% average yield per C-C coupling) by a 5-fold, Pd(0)-catalyzed, intramolecular arylation reaction. The synthesis of tetraindenocorannulene (2) follows the same course but starts from 1,2,5,6-tetrabromocorannulene. Flash vacuum pyrolysis of the intermediate 1,2,5,6-tetrakis(2-chlorophenyl)corannulene also produces tetraindenocorannulene (2). The title compounds are both deep orange, thermally robust, air stable, crystalline solids (mp >400 degrees C) with rich UV-vis spectra that have long absorption tails in the visible region.