7,7'-bis-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-9,9,9',9'-tetraoctyl-2,2'-bifluorene | 794518-80-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 7,7'-bis-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-9,9,9',9'-tetraoctyl-2,2'-bifluorene
• 英文别名: 2-[7-[9,9-Dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)fluoren-2-yl]-9,9-dioctylfluoren-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 794518-80-2
• 化学式: C₇₀H₁₀₄B₂O₄
• 分子量: 1031.22
• InChiKey: IAOJIFUYYMRDSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.49
• 重原子数：
  76
• 可旋转键数：
  31
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-溴-9-n-辛基-9H-咔唑 、 7,7'-bis-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-9,9,9',9'-tetraoctyl-2,2'-bifluorene 在 四(三苯基膦)钯 四丁基溴化铵 、 sodium carbonate 作用下， 以 水 、 甲苯 为溶剂， 以21%的产率得到7,7'-bis-[N-octyl-carbazol-3-yl]-9,9,9',9'-tetraoctyl-2,2'-bifluorene
  参考文献：
  名称：

  Novel bifluorene based conjugated systems: synthesis and properties

  摘要：

  A series of novel bifluorene based systems was synthesised by a convergent approach by means of a Suzu'ki cross-coupling between 7,7'-bis-(4,4,5,5-tetramethyl-[1,3,2]dioxaboi-olan-2-yl)-9,9,9,9'-tetraoctyl-2,2'-bifluorene and suitable aryl-bromides. All the oligomers have been characterized by H-1, C-13 NMR, Fr-IR, UV-vis, PL spectroscopy and mass analyses. In particular, it has been demonstrated that the presence of strong electron donor (amines) or withdrawing (carboxylic esters) groups causes a bathochromic shift of the optical properties with respect to those of unsubstituted molecules. The effects of these functional groups on the HOMO-LUMO energy levels were investigated by cyclic voltammetry. Remarkably, the LUMO energy level of 7,7'-bis-[5-carbodecaoxy-2,2'-bithiophen-5-yl]-9,9,9',9'-tetraoctyl-2,2'-bifluorene (-3.07 eV) is strongly influenced by the presence of the ester functional group. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.010
• 作为产物：
  描述：

  2-(7-溴-9,9-二-n-辛基-9H-芴-2-基)-4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷,2-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)-7-溴-9,9-二-n-辛基-9H-芴,7-溴-9,9-二-n-辛基-9H-芴-2-硼酸频哪醇酯 在 bis(1,5-cyclooctadiene)nickel (0) 1,5-cis,cis-cyclooctadiene 、 1,1'-bipyridyl 作用下， 以 甲苯 为溶剂， 以87%的产率得到7,7'-bis-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-9,9,9',9'-tetraoctyl-2,2'-bifluorene
  参考文献：
  名称：

  Novel bifluorene based conjugated systems: synthesis and properties

  摘要：

  A series of novel bifluorene based systems was synthesised by a convergent approach by means of a Suzu'ki cross-coupling between 7,7'-bis-(4,4,5,5-tetramethyl-[1,3,2]dioxaboi-olan-2-yl)-9,9,9,9'-tetraoctyl-2,2'-bifluorene and suitable aryl-bromides. All the oligomers have been characterized by H-1, C-13 NMR, Fr-IR, UV-vis, PL spectroscopy and mass analyses. In particular, it has been demonstrated that the presence of strong electron donor (amines) or withdrawing (carboxylic esters) groups causes a bathochromic shift of the optical properties with respect to those of unsubstituted molecules. The effects of these functional groups on the HOMO-LUMO energy levels were investigated by cyclic voltammetry. Remarkably, the LUMO energy level of 7,7'-bis-[5-carbodecaoxy-2,2'-bithiophen-5-yl]-9,9,9',9'-tetraoctyl-2,2'-bifluorene (-3.07 eV) is strongly influenced by the presence of the ester functional group. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.010

文献信息

• Novel bifluorene based conjugated systems: synthesis and properties
  作者：Roberto Grisorio、Antonio Dell'Aquila、Giuseppe Romanazzi、Gian Paolo Suranna、Piero Mastrorilli、Pynalisa Cosma、Domenico Acierno、Eugenio Amendola、Giuseppe Ciccarella、Cosimo Francesco Nobile

  DOI：10.1016/j.tet.2005.10.010

  日期：2006.1

  A series of novel bifluorene based systems was synthesised by a convergent approach by means of a Suzu'ki cross-coupling between 7,7'-bis-(4,4,5,5-tetramethyl-[1,3,2]dioxaboi-olan-2-yl)-9,9,9,9'-tetraoctyl-2,2'-bifluorene and suitable aryl-bromides. All the oligomers have been characterized by H-1, C-13 NMR, Fr-IR, UV-vis, PL spectroscopy and mass analyses. In particular, it has been demonstrated that the presence of strong electron donor (amines) or withdrawing (carboxylic esters) groups causes a bathochromic shift of the optical properties with respect to those of unsubstituted molecules. The effects of these functional groups on the HOMO-LUMO energy levels were investigated by cyclic voltammetry. Remarkably, the LUMO energy level of 7,7'-bis-[5-carbodecaoxy-2,2'-bithiophen-5-yl]-9,9,9',9'-tetraoctyl-2,2'-bifluorene (-3.07 eV) is strongly influenced by the presence of the ester functional group. (c) 2005 Elsevier Ltd. All rights reserved.