N,N-双(4-溴苯基)-4-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)苯胺 | 850153-24-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N,N-双(4-溴苯基)-4-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)苯胺
• 英文名称: 4-bromo-N-(4-bromophenyl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline
• 英文别名: pinacol [4-(bis(4-bromophenyl)amino)phenyl]boronate；2-[4-[Bis(4-bromophenyl)amino]phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；N,N-bis(4-bromophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• CAS: 850153-24-1
• 化学式: C₂₄H₂₄BBr₂NO₂
• 分子量: 529.079
• InChiKey: XVOQIMZHMJQJEC-UHFFFAOYSA-N

物化性质

• 熔点：
  146.0 to 150.0 °C
• 沸点：
  581.3±45.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.98
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-双(4-溴苯基)-4-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)苯胺 、 3-(5-bromothiophen-2-yl)-2,5-bis(2-ethylhexyl)-6-(5'-octyl-2,2'-bithiophen-5-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以60.5%的产率得到1-[5-[4-(4-bromo-N-(4-bromophenyl)anilino)phenyl]thiophen-2-yl]-2,5-bis(2-ethylhexyl)-4-[5-(5-octylthiophen-2-yl)thiophen-2-yl]pyrrolo[3,4-c]pyrrole-3,6-dione
  参考文献：
  名称：

  带隙隙的三苯胺-alt-苯并[1,2-b：4,5-b']二噻吩共聚物，待用于高效聚合物太阳能电池的苯并噻二唑或二酮吡咯并吡咯单元

  摘要：

  两个新的侧链供体-受体（d-A）系triphenylamine- ALT -苯并[1,2 b：4,5- b ']二噻吩（TPA- ALT -BDT）共聚物（P1和P2）具有侧通过Stille偶联聚合反应，合成了TPA单元中的苯并噻二唑（BT）/二酮吡咯并吡咯（DPP）。研究了它们的热，光物理，电化学，共混膜形态和光伏性能。通过使用共聚物作为供体材料和PC 71 BM作为受体的溶液法，获得了高效的本体异质结聚合物太阳能电池（PSC）。开路电压（V oc）最高时的最大功率转换效率（PCE）为3.17％）0.86V的在观察到P1为基础的省电类别，而最大短路电流（Ĵ SC的10.77毫安厘米）-2在展出P2为基础的的PSC AM1.5的照射下，100毫瓦厘米-2。交替的二元供体单元和未决的受体基团在调节此类基于D-A的侧链共聚物的光伏性质中起着重要作用。©2013 Wiley Periodicals，Inc

  DOI：

  10.1002/pola.26817
• 作为产物：
  描述：

  三(4-溴苯基)胺 在 正丁基锂 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 N,N-双(4-溴苯基)-4-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)苯胺
  参考文献：
  名称：

  Toward High Molecular Weight Triphenylamine-Based Hyperbranched Polymers

  摘要：

  Two kinds of triphenylamine-containing AB(2) monomers carrying or not carrying flexible alkyl chains were synthesized and fully characterized. One-pot Suzuki polycondensation (SPC) was applied to polymerize these monomers to prepare hyperbranched polymers. Hyperbranched polymers from AB(2) monomer not carrying alkyl chains exhibited poor solubility in common organic solvents such as THF, chloroform, toluene, etc. The poor solubility of the hyperbranched polymers hampered their applications and the further modification of the end groups. The introduction of difunctional core molecules, such as 9,9-dioctylfluorene and 9,9-dioctylfluorene trimer, in the polymerization process controlled the molecular weight and forced the hyperbranched copolymers soluble in common organic solvents mentioned above, but high molecular weight polymers could not be obtained. SPC of the AB2 monomers carrying flexible alkyl chains afforded high molecular weight fluorene-triphenylamine (F-TPA) alternating hyperbranched copolymers, which are fully soluble in common organic solvents, and their peripheral bromo functional groups can be further modified. The structures of the hyperbranched polymers were fully characterized by NMR, GPC, and combustion analysis. Initial studies on the thermal and the optical properties of the hyperbranched polymers were also reported.

  DOI：

  10.1021/ma048648+

文献信息

• Reduced-bandgap triphenylamine-<i>alt</i> -benzo[1,2-<i>b</i> :4,5-<i>b</i> ′]dithiophene copolymers pending benzothiadiazole or diketopyrrolopyrrole units for efficient polymer solar cells
  作者：Kaixuan Nie、Hua Tan、Xianping Deng、Yafei Wang、Qing Chen、Ying Huang、Yu Liu、Chuncheng Yang、Zhenrong Huang、Meixiang Zhu、Weiguo Zhu

  DOI：10.1002/pola.26817

  日期：2013.10

  triphenylamine‐alt‐benzo[1,2‐b:4,5‐b′]dithiophene (TPA‐alt‐BDT) copolymers (P1 and P2) with pendant benzothiadiazole (BT)/diketopyrrolopyrrole (DPP) in TPA unit were synthesized by Stille coupling polymerization. Their thermal, photophysical, electrochemical, blend film morphology and photovoltaic properties were investigated. Efficient bulk heterojunction polymer solar cells (PSCs) were obtained by solution

  两个新的侧链供体-受体（d-A）系triphenylamine- ALT -苯并[1,2 b：4,5- b ']二噻吩（TPA- ALT -BDT）共聚物（P1和P2）具有侧通过Stille偶联聚合反应，合成了TPA单元中的苯并噻二唑（BT）/二酮吡咯并吡咯（DPP）。研究了它们的热，光物理，电化学，共混膜形态和光伏性能。通过使用共聚物作为供体材料和PC 71 BM作为受体的溶液法，获得了高效的本体异质结聚合物太阳能电池（PSC）。开路电压（V oc）最高时的最大功率转换效率（PCE）为3.17％）0.86V的在观察到P1为基础的省电类别，而最大短路电流（Ĵ SC的10.77毫安厘米）-2在展出P2为基础的的PSC AM1.5的照射下，100毫瓦厘米-2。交替的二元供体单元和未决的受体基团在调节此类基于D-A的侧链共聚物的光伏性质中起着重要作用。©2013 Wiley Periodicals，Inc
• Starburst Triphenylamine-Based Donor-Acceptor-Type Small Molecules for Solution-Processed Organic Solar Cells
  作者：Hua Tan、Wenhong Peng、Manjun Xiao、Chao Xu、Kaixuan Nie、Junting Yu、Yafei Wang、Yu Liu、Weiguo Zhu

  DOI：10.1002/ejoc.201501376

  日期：2016.2

  A class of the donor–acceptor (D–A)-type organic small molecules that includes TPA-DPP, DTPA-DPP, and TTPA-DPP [TPA = triphenylamine, DPP = diketopyrrolopyrrole, DTPA = bis(triphenylamine), TTPA = tris(triphenylamine)] was synthesized; these compounds contain TPA as a donor unit and DPP as an acceptor unit. Solution-processed organic solar cells (OSCs) with these compounds as donors and [6,6]-phenyl-C71-butyric

  一类供体-受体 (D-A) 型有机小分子，包括 TPA-DPP、DTPA-DPP 和 TTPA-DPP [TPA = 三苯胺，DPP = 二酮吡咯并吡咯，DTPA = 双（三苯胺），TTPA = 三(三苯胺)]合成；这些化合物包含 TPA 作为供体单元和 DPP 作为受体单元。以这些化合物为供体、[6,6]-苯基-C71-丁酸甲酯（PC71BM）为受体的溶液处理有机太阳能电池（OSC）被制造出来。DTPA-DPP 和 TTPA-DPP 分别用两个和三个 TPA 单元制备的星爆 OSCs 表现出比用一个 TPA 单元制备的 OSC 更好的光伏性能，因为 DTPA-DPP 和 TTPA-DPP 具有更好的光捕获性能和电荷- 运输特性。基于 DTPA-DPP 的 OSC 的功率转换效率 (PCE) 为 2。26% 和基于 TTPA-DPP 的 OSC 表现出更高的 PCE，为 2.47%。PCE
• Toward High Molecular Weight Triphenylamine-Based Hyperbranched Polymers
  作者：Minghao Sun、Jing Li、Binsong Li、Yaqin Fu、Zhishan Bo

  DOI：10.1021/ma048648+

  日期：2005.4.1

  Two kinds of triphenylamine-containing AB(2) monomers carrying or not carrying flexible alkyl chains were synthesized and fully characterized. One-pot Suzuki polycondensation (SPC) was applied to polymerize these monomers to prepare hyperbranched polymers. Hyperbranched polymers from AB(2) monomer not carrying alkyl chains exhibited poor solubility in common organic solvents such as THF, chloroform, toluene, etc. The poor solubility of the hyperbranched polymers hampered their applications and the further modification of the end groups. The introduction of difunctional core molecules, such as 9,9-dioctylfluorene and 9,9-dioctylfluorene trimer, in the polymerization process controlled the molecular weight and forced the hyperbranched copolymers soluble in common organic solvents mentioned above, but high molecular weight polymers could not be obtained. SPC of the AB2 monomers carrying flexible alkyl chains afforded high molecular weight fluorene-triphenylamine (F-TPA) alternating hyperbranched copolymers, which are fully soluble in common organic solvents, and their peripheral bromo functional groups can be further modified. The structures of the hyperbranched polymers were fully characterized by NMR, GPC, and combustion analysis. Initial studies on the thermal and the optical properties of the hyperbranched polymers were also reported.