5,5′-bis-(2,3,4,5-tetraphenylborole)-2,2′-bithiophene | 1412912-75-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 5,5′-bis-(2,3,4,5-tetraphenylborole)-2,2′-bithiophene
• 英文别名: 2-(2,3,4,5-Tetraphenylborol-1-yl)-5-[5-(2,3,4,5-tetraphenylborol-1-yl)thiophen-2-yl]thiophene；2-(2,3,4,5-tetraphenylborol-1-yl)-5-[5-(2,3,4,5-tetraphenylborol-1-yl)thiophen-2-yl]thiophene
• CAS: 1412912-75-4
• 化学式: C₆₄H₄₄B₂S₂
• 分子量: 898.807
• InChiKey: YYCYDESYKQBFDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.51
• 重原子数：
  68
• 可旋转键数：
  11
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-二甲氨基吡啶 、 5,5′-bis-(2,3,4,5-tetraphenylborole)-2,2′-bithiophene 以 二氯甲烷 为溶剂， 以88%的产率得到5,5′-bis-(2,3,4,5-tetraphenylborole)-2,2′-bithiophene-bis(dimethylaminopyridine)
  参考文献：
  名称：

  1-Heteroaromatic-Substituted Tetraphenylboroles: π–π Interactions Between Aromatic and Antiaromatic Rings Through a B–C Bond

  摘要：

  A series of 2,3,4,5-tetraphenylboroles substituted with different aromatic heterocycles (thiophene, furan, pyrrole, and dithiophene) in the 1-position were synthesized and characterized by means of NMR, elemental analysis, and X-ray crystallography. In contrast to known 2,3,4,5-tetraphenylboroles, X-ray diffraction revealed a nearly coplanar arrangement of the aromatic heterocycles and the antiaromatic borole scaffold as a result of pi-conjugation, which could be substantiated by DFT calculations. Furthermore, the 2,2'-dithiophene-bridged bisborole (14) exhibits a large bathochromic shift in the absorption spectrum, demonstrating the exceptional Lewis acidity of the nonannulated borolyl moiety.

  DOI：

  10.1021/ja309935t
• 作为产物：
  描述：

  5,5′-bis(dichloroboryl)-2,2′-bithiophene 、 1,1-dimethyl-2,3,4,5-tetraphenylstannole 以 二氯甲烷 为溶剂， 反应 3.0h， 以75%的产率得到5,5′-bis-(2,3,4,5-tetraphenylborole)-2,2′-bithiophene
  参考文献：
  名称：

  1-Heteroaromatic-Substituted Tetraphenylboroles: π–π Interactions Between Aromatic and Antiaromatic Rings Through a B–C Bond

  摘要：

  A series of 2,3,4,5-tetraphenylboroles substituted with different aromatic heterocycles (thiophene, furan, pyrrole, and dithiophene) in the 1-position were synthesized and characterized by means of NMR, elemental analysis, and X-ray crystallography. In contrast to known 2,3,4,5-tetraphenylboroles, X-ray diffraction revealed a nearly coplanar arrangement of the aromatic heterocycles and the antiaromatic borole scaffold as a result of pi-conjugation, which could be substantiated by DFT calculations. Furthermore, the 2,2'-dithiophene-bridged bisborole (14) exhibits a large bathochromic shift in the absorption spectrum, demonstrating the exceptional Lewis acidity of the nonannulated borolyl moiety.

  DOI：

  10.1021/ja309935t

文献信息

• 1-Heteroaromatic-Substituted Tetraphenylboroles: π–π Interactions Between Aromatic and Antiaromatic Rings Through a B–C Bond
  作者：Holger Braunschweig、Alexander Damme、J. Oscar C. Jimenez-Halla、Christian Hörl、Ivo Krummenacher、Thomas Kupfer、Lisa Mailänder、Krzysztof Radacki

  DOI：10.1021/ja309935t

  日期：2012.12.12

  A series of 2,3,4,5-tetraphenylboroles substituted with different aromatic heterocycles (thiophene, furan, pyrrole, and dithiophene) in the 1-position were synthesized and characterized by means of NMR, elemental analysis, and X-ray crystallography. In contrast to known 2,3,4,5-tetraphenylboroles, X-ray diffraction revealed a nearly coplanar arrangement of the aromatic heterocycles and the antiaromatic borole scaffold as a result of pi-conjugation, which could be substantiated by DFT calculations. Furthermore, the 2,2'-dithiophene-bridged bisborole (14) exhibits a large bathochromic shift in the absorption spectrum, demonstrating the exceptional Lewis acidity of the nonannulated borolyl moiety.