2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-decylcarbazole | 1258942-43-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-decylcarbazole
• 英文别名: 9-decyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)carbazole；N-decyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)carbazole；9-Decyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole；9-decyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole
• CAS: 1258942-43-6
• 化学式: C₃₄H₅₁B₂NO₄
• 分子量: 559.405
• InChiKey: AALGSWZIVSNKGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.53
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  41.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,7-dibromo-9-decyl-9H-carbazole 、 联硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 以71%的产率得到2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-decylcarbazole
  参考文献：
  名称：

  半导体控制的单壁碳纳米管的直径选择性分散

  摘要：

  研究了一系列严格交替的共聚物选择性包裹单壁碳纳米管（SWNT）的能力。通过Suzuki交叉偶联方案，以高收率获得了包含被萘，蒽和蒽醌间隔基分隔开的芴或咔唑亚基的七种共聚物。引入1，5-连接的萘，蒽和蒽醌单元以有利于聚合物主链的螺旋构象，以改善其SWNT包裹特性。使用萘-1,5-二甲苯磺酸盐前体可获得特别高的聚合物产率，这突出了双官能芳基三氟甲磺酸酯作为共聚物前体的潜力。所有聚合物均将HiPco SWNTs分散在甲苯中。通过密度梯度离心法纯化获得的分散体，并通过光致发光（PL）光谱分析其组成。在其分散能力方面，聚合物或多或少显示出显着的SWNT直径选择性。特别是，聚（9,9-二癸基芴-2,7-二基-ALT -蒽-1,5-二基）（P2）呈现朝向具有直径为≥0.95纳米的单壁碳纳米管，包括贴近Z字形纳米管选择性强。通过吸光度和拉曼散射光谱进一步分析P2的SWNT分散体。直径选择性归因于蒽-1,5

  DOI：

  10.1021/cm200275v

文献信息

• Selective Dispersion of Single-Walled Carbon Nanotubes with Specific Chiral Indices by Poly(<i>N</i>-decyl-2,7-carbazole)
  作者：Fabien A. Lemasson、Timo Strunk、Peter Gerstel、Frank Hennrich、Sergei Lebedkin、Christopher Barner-Kowollik、Wolfgang Wenzel、Manfred M. Kappes、Marcel Mayor

  DOI：10.1021/ja105722u

  日期：2011.2.2

  Physico-chemical methods to sort single-walled carbon nanotubes (SWNTs) by chiral index are presently lacking but are required for in-depth experimental analysis and also for potential future applications of specific species. Here we report the unexpected selectivity of poly(N-decyl-2,7-carbazole) to almost exclusively disperse semi-conducting SWNTs with differences of their chiral indices (n - m) >= 2 in toluene. The observed selectivity complements perfectly the dispersing features of the fluorene analogue poly(9,9-dialkyl-2,7-fluorene), which disperses semiconducting SWNTs with (n - m) <= 2 in toluene. The dispersed samples are further purified by density gradient centrifugation and analyzed by photoluminescence excitation spectroscopy. All-atom molecular modeling with decamer model compounds of the polymers and (10,2) and (7,6) SWNTs suggests differences in the pi-pi stacking interaction as origin of the selectivity. We observe energetically favored complexes between the (10,2) SWNT and the carbazole decamer and between the (7,6) SWNT and the fluorene decamer, respectively. These findings demonstrate that subtle structural changes of polymers lead to selective solvation of different families of carbon nanotubes. Furthermore, chemical screening of closely related polymers may pave the way toward simple, low-cost, and index-specific isolation of SWNTs.
• Copolymer-Controlled Diameter-Selective Dispersion of Semiconducting Single-Walled Carbon Nanotubes
  作者：Nicolas Berton、Fabien Lemasson、Jana Tittmann、Ninette Stürzl、Frank Hennrich、Manfred M. Kappes、Marcel Mayor

  DOI：10.1021/cm200275v

  日期：2011.4.26

  nanotubes (SWNTs) is investigated. Seven copolymers comprising either fluorene or carbazole subunits separated by naphthalene, anthracene, and anthraquinone spacers are obtained in good yields via a Suzuki cross-coupling protocol. The 1,5-linked naphthalene, anthracene, and anthraquinone units are introduced to favor a spiral conformation of the polymer backbone in order to improve its SWNT wrapping

  研究了一系列严格交替的共聚物选择性包裹单壁碳纳米管（SWNT）的能力。通过Suzuki交叉偶联方案，以高收率获得了包含被萘，蒽和蒽醌间隔基分隔开的芴或咔唑亚基的七种共聚物。引入1，5-连接的萘，蒽和蒽醌单元以有利于聚合物主链的螺旋构象，以改善其SWNT包裹特性。使用萘-1,5-二甲苯磺酸盐前体可获得特别高的聚合物产率，这突出了双官能芳基三氟甲磺酸酯作为共聚物前体的潜力。所有聚合物均将HiPco SWNTs分散在甲苯中。通过密度梯度离心法纯化获得的分散体，并通过光致发光（PL）光谱分析其组成。在其分散能力方面，聚合物或多或少显示出显着的SWNT直径选择性。特别是，聚（9,9-二癸基芴-2,7-二基-ALT -蒽-1,5-二基）（P2）呈现朝向具有直径为≥0.95纳米的单壁碳纳米管，包括贴近Z字形纳米管选择性强。通过吸光度和拉曼散射光谱进一步分析P2的SWNT分散体。直径选择性归因于蒽-1,5