2,7-二硼酸频哪醇酯-9-辛基咔唑 | 871696-12-7

• 物质功能分类: 医药中间体 - OLED材料中间体
• 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
• 中文名称: 2,7-二硼酸频哪醇酯-9-辛基咔唑
• 英文名称: N-hexyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole
• 英文别名: 9-Hexyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole；9-hexyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole
• CAS: 871696-12-7
• 化学式: C₃₀H₄₃B₂NO₄
• 分子量: 503.298
• InChiKey: VUJPSYQJTJSPOI-UHFFFAOYSA-N

物化性质

• 熔点：
  221.0 to 225.0 °C
• 沸点：
  587.6±43.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  41.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  dichloro( 1,5-cyclooctadiene)platinum(ll) 、 2,7-二硼酸频哪醇酯-9-辛基咔唑 在 cesium fluoride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  [4]环-N-烷基-2,7-咔唑：烷基链长度对结构、电子和电荷传输特性的影响

  摘要：

  具有径向 π 轨道的大环经历了惊人的发展。然而，它们在有机电子器件中的结合仍然非常稀少。在这项工作中，我们的目标是通过报告基于纳米环系统的有机功能材料的第一个详细结构-性能-器件性能关系研究来弥合有机电子和纳米环之间的差距。三[4]环-N已经合成了在其氮原子上带有不同烷基链的-烷基-2,7-咔唑，并通过结合实验和理论方法进行了表征。这项研究包括电化学、光物理、热和结构固态测量以及电荷传输特性研究。Pt 方法的优化方案已被开发以高产率 (52-64%) 合成 [4] 环咔唑，这对纳米环的进一步发展，特别是在材料科学中具有重要意义。已经研究了[4]环咔唑和模型化合物[8]环对亚苯基( [8]CPP )的电荷传输特性。虽然没有记录到基准[8]CPP 的场效应 (FE) 迁移率，但大约 FE 迁移率值。10 –5厘米2 ·V –1 ·s –1记录为 [4] 环咔唑。记录的三个 [4] 环咔唑的特性（阈值电压V

  DOI：

  10.1021/jacs.1c03240
• 作为产物：
  描述：

  2,7-二溴咔唑 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2,7-二硼酸频哪醇酯-9-辛基咔唑
  参考文献：
  名称：

  Carbazole-linked porphyrin dimers for organic light emitting diodes: synthesis and initial photophysical studies

  摘要：

  Carbazole linked porphyrin dimers were synthesized in good yields via stepwise Suzuki coupling reactions using bromoporphyrins and borylated carbazoles as the precursors, the latter of which were synthesized via known procedures from biphenyl derivatives. For comparative purposes porphyrin-carbazole monomers were synthesized. Single layer organic light emitting diodes (OLEDs) were created to demonstrate the optical properties of these materials. Light emission from these carbazole substituted porphyrins showed better results compared to previously examined bromo substituted porphyrins with better electroluminescence and lower turn-on voltages. Dimers exhibited turn-on voltages of 3 V compared to 6 V for monomeric porphyrin-carbazoles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.096

文献信息

• Conjugated Ladder-Type Heteroacenes Bearing Pyrrole and Thiophene Ring Units: Facile Synthesis and Characterization
  作者：Peng Gao、Xinliang Feng、Xiaoyin Yang、Volker Enkelmann、Martin Baumgarten、Klaus Müllen

  DOI：10.1021/jo801898g

  日期：2008.12.5

  Ladder-type heteroacenes containing pyrrole and thiophene rings, dibenzo[b,b']thieno[2,3-f:5,4-f']-carbazoles (DBTCZ, 1), and diindolo[3,2-b:2',3'-h]benzo[1,2-b:4,5-b']bis[1]benzothiophene (DIBBBT, 2), were facilely synthesized through proper precursors (7, 11, and 18) respectively. The key step is a triflic acid induced intramolecular electrophilic coupling reaction of corresponding aromatic methyl

  包含吡咯和噻吩环，二苯并[b，b']噻吩并[2,3-f：5,4-f']-咔唑（DBTCZ，1）和二吲哚[3,2-b：2 '，3'-h]苯并[1,2-b：4,5-b']双[1]苯并噻吩（DIBBBT，2）分别通过适当的前体（7、11和18）轻松合成。关键步骤是三氟甲磺酸引起的相应芳族甲基亚砜与活化的芳族结构单元的分子内亲电偶联反应，从而能够进行区域选择性的闭环。朝向DBTCZ的两种前体（7和11）均给出了对称产物，但具有以两种不同方式增溶的烷基链。DIBBBT也被合成为具有确定结构的扩展梯型杂并苯。这些获得的杂苯具有充分的特征（质谱，NMR，元素分析），
• Systematic Structure–Property Investigations on a Series of Alternating Carbazole–Thiophene Oligomers
  作者：Shin-ichiro Kato、Satoru Shimizu、Atsushi Kobayashi、Toshitada Yoshihara、Seiji Tobita、Yosuke Nakamura

  DOI：10.1021/jo402416f

  日期：2014.1.17

  A series of alternating carbazole-thiophene oligomers, namely 2,7-linked carbazole-thiophene oligomers 1, 3, 5, 7, and 9 and 3,6-linked ones 2, 4, 6, 8, and 10, in which the molecular length was systematically elongated, were synthesized by Suzuki-Miyaura coupling reactions. The effects of the conjugation connectivity between the carbazole and thiophene moieties and the molecular length on the electronic, photophysical, and electrochemical properties of 1-10 were comprehensively investigated. In the present oligomer architectures, the connection with thiophene at the 2,7-positions of carbazole ensures pi-conjugation to a high extent and high fluorescence quantum yields, while that at the 3,6-positions enhances the donor ability. The increase in the molecular length of the 2,7-linked oligomers effectively extends pi-conjugation. The relationship between structural variations and photophysical properties was examined by fluorescence lifetime measurements in detail. The X-ray crystal structure of 6 was also disclosed.
• CN115772112
  申请人：——

  公开号：——

  公开（公告）日：——
• [4]Cyclo-<i>N</i>-alkyl-2,7-carbazoles: Influence of the Alkyl Chain Length on the Structural, Electronic, and Charge Transport Properties
  作者：Fabien Lucas、Nemo McIntosh、Emmanuel Jacques、Christophe Lebreton、Benoît Heinrich、Bertrand Donnio、Olivier Jeannin、Joëlle Rault-Berthelot、Cassandre Quinton、Jérôme Cornil、Cyril Poriel

  DOI：10.1021/jacs.1c03240

  日期：2021.6.16

  values of ca. 10–5 cm2·V–1·s–1 were recorded for the [4]cyclocarbazoles. The characteristics (threshold voltage VTH, subthreshold swing SS, trapping energy ΔE) recorded for the three [4]cyclocarbazoles appear to be modulated by the alkyl chain length borne by the nitrogen atoms. Remarkably, the space-charge-limited current mobilities measured for the [4]cyclocarbazoles are about 3 orders of magnitude higher

  具有径向 π 轨道的大环经历了惊人的发展。然而，它们在有机电子器件中的结合仍然非常稀少。在这项工作中，我们的目标是通过报告基于纳米环系统的有机功能材料的第一个详细结构-性能-器件性能关系研究来弥合有机电子和纳米环之间的差距。三[4]环-N已经合成了在其氮原子上带有不同烷基链的-烷基-2,7-咔唑，并通过结合实验和理论方法进行了表征。这项研究包括电化学、光物理、热和结构固态测量以及电荷传输特性研究。Pt 方法的优化方案已被开发以高产率 (52-64%) 合成 [4] 环咔唑，这对纳米环的进一步发展，特别是在材料科学中具有重要意义。已经研究了[4]环咔唑和模型化合物[8]环对亚苯基( [8]CPP )的电荷传输特性。虽然没有记录到基准[8]CPP 的场效应 (FE) 迁移率，但大约 FE 迁移率值。10 –5厘米2 ·V –1 ·s –1记录为 [4] 环咔唑。记录的三个 [4] 环咔唑的特性（阈值电压V
• Carbazole-linked porphyrin dimers for organic light emitting diodes: synthesis and initial photophysical studies
  作者：Aoife Ryan、Brian Tuffy、Sabine Horn、Werner J. Blau、Mathias O. Senge

  DOI：10.1016/j.tet.2011.08.096

  日期：2011.10

  Carbazole linked porphyrin dimers were synthesized in good yields via stepwise Suzuki coupling reactions using bromoporphyrins and borylated carbazoles as the precursors, the latter of which were synthesized via known procedures from biphenyl derivatives. For comparative purposes porphyrin-carbazole monomers were synthesized. Single layer organic light emitting diodes (OLEDs) were created to demonstrate the optical properties of these materials. Light emission from these carbazole substituted porphyrins showed better results compared to previously examined bromo substituted porphyrins with better electroluminescence and lower turn-on voltages. Dimers exhibited turn-on voltages of 3 V compared to 6 V for monomeric porphyrin-carbazoles. (C) 2011 Elsevier Ltd. All rights reserved.