indacenopicene | 317823-30-6

• 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: indacenopicene
• 英文别名: as-indaceno[3,2,1,8,7,6-pqrstuv]picene；indaceno[3,2,1,8,7,6pqrstuv]picene；As-indaceno[3,2,1,8,7,6-pqrstuv]picene；octacyclo[16.8.0.02,7.03,25.06,10.08,17.09,14.021,26]hexacosa-1(18),2,4,6,8(17),9(14),10,12,15,19,21(26),22,24-tridecaene
• CAS: 317823-30-6
• 化学式: C₂₆H₁₂
• 分子量: 324.381
• InChiKey: UGXFPHUOIVNTMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  8.0
• 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：

  四氢呋喃 、 18-冠醚-6 、 indacenopicene 、 caesium 以 正己烷 为溶剂， 反应 8.0h， 以65%的产率得到
  参考文献：
  名称：

  From Corannulene to Indacenopicene: Effect of Carbon Framework Topology on Aromaticity and Reduction Limits

  摘要：

  The electronic structure, reduction limits, and coordination abilities of a bowl-shaped polycyclic aromatic hydrocarbon, indacenopicene (C26H12, 1), have been investigated for the first time using a combination of theoretical and experimental tools. A direct comparison with the prototypical corannulene bowl (C20H10, 2) revealed the effects of carbon framework topology and symmetry change on the electronic properties and aromaticity of indacenopicene. The accessibility of two reduction steps for 1 was predicted theoretically and then confirmed experimentally. Two reversible one-electron reduction processes with the formal reduction potentials at -1.92 and -2.29 V vs Fc(+/0) were detected by cyclic voltammetry measurements, demonstrating the stability of the corresponding, mono- and dianionic states of 1. The products of the doubly reduced indacenopicene have been isolated as rubidium and cesium,salts and fully characterized. Their X-ray diffraction study revealed the formation of tetranuclear organometallic building blocks with the [M-2(18-crown-6)](2+) (M = Rb (3) and Cs (4)) cations occupying the concave cavities of two C26H122- anions. The coordination of two outside exo-bound rubidium ions is terminated by crown ether molecules in 3 to form the discrete [Rb-4(+)(18-crown-6)(3)(C26H122-](2) tetramer. In contrast, the larger cesium ions allow the 1D polymeric chain propagation in 4 to afford [Cs-2(+)(18-crown-6)(2)(THF)(C26H122-)](infinity).

  DOI：

  10.1021/acs.organomet.6b00395
• 作为产物：
  描述：

  1,4-difluoro-6-methylbenzo[c]phenanthrene 在 aluminum oxide 、 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 、 碘 、 methyloxirane 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙醇 、 环己烷 、 邻二氯苯 为溶剂， 反应 30.5h， 生成 indacenopicene
  参考文献：
  名称：

  化学选择性芳香族CF键活化合成合理卤代的水杯

  摘要：

  卤化Buckybowls或碗形多环芳烃（BS‐PAHs）是“自下而上”合成各种碳基纳米材料的关键组成部分，这些碳基纳米材料在不同的技术领域均具有巨大的潜力。当前的最新技术为BS-PAH提供了数量有限的合成途径。此外，这些方法均未显示出高选择性和对官能团的耐受性。在本文中，我们证明了一种通向BS-PAHs的有效途径，包括通过C-F键激活的定向分子内芳基-芳基偶联。发现偶合条件完全耐受芳族C-Br和C-Cl键，因此可以以前所未有的选择性水平轻松合成合理卤化的巴基杯。

  DOI：

  10.1002/anie.201700814

文献信息

• Facile Bucky-Bowl Synthesis by Regiospecific Cove-Region Closure by HF Elimination
  作者：K. Yu. Amsharov、M. A. Kabdulov、Martin Jansen

  DOI：10.1002/anie.201200516

  日期：2012.5.7

  intramolecular aryl–aryl coupling is the key step in rational fullerene synthesis and in synthesis of extended buckybowl structures. Such a process can be embodied very efficiently through quantitative HF elimination on active Al2O3. The process is characterized by an unprecedentedly high chemoselectivity and regiospecificity.

  积木：有效的分子内芳基-芳基偶联是合理的富勒烯合成和延伸的Buckybowl结构合成中的关键步骤。通过对活性Al 2 O 3进行定量的HF消除，可以非常有效地实现这一过程。该过程的特点是前所未有的高化学选择性和区域特异性。
• Acenaphthenoannulation Induced by the Dual Lewis Acidity of Alumina
  作者：Vladimir Akhmetov、Mikhail Feofanov、Cordula Ruppenstein、Josefine Lange、Dmitry Sharapa、Marjan Krstić、Frank Hampel、Evgeny A. Kataev、Konstantin Amsharov

  DOI：10.1002/chem.202200584

  日期：2022.6

  We have discovered a dual (i. e., soft and hard) Lewis acidity of alumina that enables rapid one-pot π-extension through the activation of terminal alkynes followed by C-F activation. The tandem reaction introduces an acenaphthene fragment - an essential moiety of geodesic polyarenes. This reaction provides quick access to elusive non-alternant polyarenes such as π-extended buckybowls and helicenes

  我们发现了氧化铝的双重（即软和硬）路易斯酸度，可以通过末端炔烃的活化和 CF 活化来实现快速的一锅 π 延伸。串联反应引入了苊片段——测地线聚芳烃的重要部分。该反应通过 1-(2-乙炔基-6-氟苯基)萘部分的三点环化，快速获得难以捉摸的非交替聚芳烃，例如 π 延伸的巴基碗和螺旋烯。通过合成难以捉摸的测地线石墨烯纳米带的前所未有的结构片段，证明了所开发方法的多功能性。
• From Corannulene to Indacenopicene: Effect of Carbon Framework Topology on Aromaticity and Reduction Limits
  作者：Sarah N. Spisak、Jingbai Li、Andrey Yu. Rogachev、Zheng Wei、Olena Papaianina、Konstantin Amsharov、Alexey V. Rybalchenko、Alexey A. Goryunkov、Marina A. Petrukhina

  DOI：10.1021/acs.organomet.6b00395

  日期：2016.9.26

  The electronic structure, reduction limits, and coordination abilities of a bowl-shaped polycyclic aromatic hydrocarbon, indacenopicene (C26H12, 1), have been investigated for the first time using a combination of theoretical and experimental tools. A direct comparison with the prototypical corannulene bowl (C20H10, 2) revealed the effects of carbon framework topology and symmetry change on the electronic properties and aromaticity of indacenopicene. The accessibility of two reduction steps for 1 was predicted theoretically and then confirmed experimentally. Two reversible one-electron reduction processes with the formal reduction potentials at -1.92 and -2.29 V vs Fc(+/0) were detected by cyclic voltammetry measurements, demonstrating the stability of the corresponding, mono- and dianionic states of 1. The products of the doubly reduced indacenopicene have been isolated as rubidium and cesium,salts and fully characterized. Their X-ray diffraction study revealed the formation of tetranuclear organometallic building blocks with the [M-2(18-crown-6)](2+) (M = Rb (3) and Cs (4)) cations occupying the concave cavities of two C26H122- anions. The coordination of two outside exo-bound rubidium ions is terminated by crown ether molecules in 3 to form the discrete [Rb-4(+)(18-crown-6)(3)(C26H122-](2) tetramer. In contrast, the larger cesium ions allow the 1D polymeric chain propagation in 4 to afford [Cs-2(+)(18-crown-6)(2)(THF)(C26H122-)](infinity).
• Synthesis of Rationally Halogenated Buckybowls by Chemoselective Aromatic C−F Bond Activation
  作者：Olena Papaianina、Vladimir A. Akhmetov、Alexey A. Goryunkov、Frank Hampel、Frank W. Heinemann、Konstantin Y. Amsharov

  DOI：10.1002/anie.201700814

  日期：2017.4.18

  carbon‐based nanomaterials with outstanding potential in different fields of technology. The current state of the art provides quite a limited number of synthetic pathways to BS‐PAHs; moreover, none of these approaches show high selectivity and tolerance of functional groups. Herein we demonstrate an effective route to BS‐PAHs that includes directed intramolecular aryl–aryl coupling through C−F bond

  卤化Buckybowls或碗形多环芳烃（BS‐PAHs）是“自下而上”合成各种碳基纳米材料的关键组成部分，这些碳基纳米材料在不同的技术领域均具有巨大的潜力。当前的最新技术为BS-PAH提供了数量有限的合成途径。此外，这些方法均未显示出高选择性和对官能团的耐受性。在本文中，我们证明了一种通向BS-PAHs的有效途径，包括通过C-F键激活的定向分子内芳基-芳基偶联。发现偶合条件完全耐受芳族C-Br和C-Cl键，因此可以以前所未有的选择性水平轻松合成合理卤化的巴基杯。