2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-3-[4-(N,N-diphenylamino)phenyl]-acrylonitrile | 1402049-88-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-3-[4-(N,N-diphenylamino)phenyl]-acrylonitrile
• CAS: 1402049-88-0
• 化学式: C₃₃H₃₁BN₂O₂
• 分子量: 498.432
• InChiKey: FXXTZUZHOACGOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.52
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  45.49
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-3-[4-(N,N-diphenylamino)phenyl]-acrylonitrile 、 2-bromo-9,10-bis(octoloxy)anthracene 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  三苯胺附加蒽衍生物的设计：电聚合及其电致变色行为†

  摘要：

  设计并合成了蒽的三个衍生物（2-TPACNANT，2,6-TPACNANT和2,6-TPAANT）作为具有一个或两个末端三苯胺侧末端的核心内部结构，目的是为了获得电化学目的的末端活性位点聚合。p-2,6-TPACNANT和p-2,6-TPAANT的电沉积聚合物薄膜通过重复循环伏安法（CV）扫描电解质中的恒定单体溶液，可以在0至1.6 V的电压范围内获得ITO /玻璃电极上的导电性。通过控制CV扫描次数，可以轻松调整膜厚。有趣的是，这些电生成的聚合物膜在电氧化时显示出可逆的电化学响应和明显的颜色变化，通过电势调制可以切换多次。ITO上电致变色膜的光谱电化学研究表明，p-2,6-TPAANT（砖红色-深蓝色）和p-2,6-TPACNANT（橙-深蓝色）两种颜色具有较高的色彩对比度（Δ）T）p-2,6-TPAANT在770 nm时为87％p-2,6-TPACNANT分别在800 nm和86％时为

  DOI：

  10.1039/c6ra14926j
• 作为产物：
  描述：

  二苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 1,1'-双(二苯基膦)二茂铁 、 potassium acetate 、 palladium diacetate 、 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 88.5h， 生成 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-3-[4-(N,N-diphenylamino)phenyl]-acrylonitrile
  参考文献：
  名称：

  D?A?D low band gap molecule containing triphenylamine and benzoxadiazole/benzothiadiazole units: Synthesis and photophysical properties

  摘要：

  Two D-A-D-type low band gap organic dyes based on triphenylamine and benzoxadiazole/benzothiadiazole, 4,7-Bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]-1-nitrilethenyl}phenyl}-2-thienyl}-2,1,3-benzoxadiazole (BDNTBX) and 4,7-Bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]-1-nitrilethenyl}phenyl}-2-thienyl}-2,1,3-benzothiadiazole (BDNTBT) were successfully synthesized. The properties of two compounds were investigated by density functional theory (DFT) calculations, UV-vis absorption spectroscopy, cyclic voltammetry and fluorescence quenching experiment. The calculated ground-state geometries demonstrate intramolecular charge transfer (ICE) occurs in both molecules during the procedure of charge excitation from HOMO to LUMO. From the data in electrochemistry and fluorescence quenching experiments, the molecules reveal lower HOMO energy levels compared with that of P3HT and proper LUMO energy levels to obtain efficient charge separation with PCBM. Two synthesized compounds exhibit broad absorption range covering the whole visible spectral region. These photophysical and electrochemical properties call attention to that our materials are prospective candidates as donor materials for solution-processable organic photovoltaic cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.04.001

文献信息

• D–π–A–π–D type benzothiadiazole–triphenylamine based small molecules containing cyano on the π-bridge for solution-processed organic solar cells with high open-circuit voltage
  作者：Shaohang Zeng、Lunxiang Yin、Changyan Ji、Xueying Jiang、Kechang Li、Yanqin Li、Yue Wang

  DOI：10.1039/c2cc35754b

  日期：——

  Two novel D-pi-A-pi-D structured small molecules composed of benzothiadiazole and triphenylamine were designed and synthesized. with cyano on the pi-bridge exhibited a deep HOMO energy level, resulting in an impressive V(OC) of up to 1.04 V with a PCE of 3.85%, while non-cyano substituted yielded a V(OC) of 0.94 V and a PCE of 1.99%.

  设计并合成了由苯并噻二唑和三苯胺组成的两个新颖的D-pi-A-pi-D结构小分子。在pi桥上带有氰基的化合物显示出很深的HOMO能级，导致高达1.04 V的V（OC）令人印象深刻，PCE为3.85％，而未被氰基取代的V（OC）为0.94 V，且PCE为1.99％。
• Linkage effects of linear D–π–A–π–D type diketopyrrolopyrrole-triphenylamine based solution-processable organic small molecule photovoltaic materials
  作者：Changyan Ji、Lunxiang Yin、Lihui Wang、Tao Jia、Shixiang Meng、Yingji Sun、Yanqin Li

  DOI：10.1039/c3tc32214a

  日期：——

  Four novel D–π–A–π–D-type small molecules (SMs) were synthesized and their π-linkage effects were investigated. Among them, SM2 with vinylene as the π-linkage exhibited better molecular coplanarity, reaching a relatively higher power conversion efficiency (PCE) of 3.76%. SM3 and SM4 with acetylene and acrylonitrile as π-linkages exhibited relatively higher open-circuit voltages (VOC) of 0.93 V and 0.90 V, respectively, owing to their deep-lying HOMO levels. These results gave an important guide for developing new materials in solution-processed small molecule solar cells.

  研究人员合成了四种新型 DâÏâAâÏâD 型小分子（SMs），并研究了它们的Ï-连接效应。其中，以乙烯为Ï-连接键的 SM2 表现出更好的分子共面性，功率转换效率（PCE）相对较高，达到 3.76%。以乙炔和丙烯腈为Ï-连接的 SM3 和 SM4 由于具有深层 HOMO 水平，开路电压（VOC）相对较高，分别为 0.93 V 和 0.90 V。这些结果为开发溶液法小分子太阳能电池新材料提供了重要指导。
• Efficient small molecule photovoltaic donor based on 2,3-diphenyl-substituted quinoxaline core for solution-processed organic solar cells
  作者：Bao Xie、Sheng Bi、Rui Wu、Lunxiang Yin、Changyan Ji、Zhengjiang Cai、Yanqin Li

  DOI：10.1039/c7ra01859b

  日期：——

  A novel D–π–A–π–D-type organic small molecule (OSM) named (TPACN)2Qx was designed and synthesized for solution-processible organic solar cells (OSCs), which contained 2,3-diphenyl-substituted quinoxaline (Qx) as the central acceptor (A) unit, triphenylamine (TPA) as terminal electron-donor (D) moieties, and acrylonitrile as the π-linkage segment. With an effective electron-withdrawing property and

  一种新的命名为d-π-A-π-d型有机小分子（OSM）（TPACN）2 QX被设计和用于溶液加工的有机太阳能电池（OSC）中合成，其中载-2,3-二苯基喹喔啉基取代（Qx）作为中心受体（A）单元，三苯胺（TPA）作为末端电子给体（D）部分，丙烯腈作为π键链段。（TPACN）2 Qx具有有效的吸电子性能和相对稳定的Qx喹诺酮几何形状，其窄带隙为1.88 eV，在300-700 nm处具有强而宽的吸收。结果，基于（TPACN）2 Qx：PC 61获得了6.25％的出色功率转换效率（PCE）。在溶液中使用简单的旋涂工艺进行BM混合，这是迄今为止基于Qx核的溶液处理OSM光伏（PV）器件实现的最高效率。令人印象深刻的结果表明，采用喹喔啉衍生物作为亲电单元的OSM可以与其聚合物同类产品竞争。