4,7-bis(5-bromothieno [3,2-b]thiophen-2-yl)-5,6-bis(octyloxy)benzo[c][1,2,5]oxadiazole | 1443210-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 4,7-bis(5-bromothieno [3,2-b]thiophen-2-yl)-5,6-bis(octyloxy)benzo[c][1,2,5]oxadiazole
• 英文别名: 4,7-Bis(5-bromothieno[3,2-b]thiophen-2-yl)-5,6-dioctoxy-2,1,3-benzoxadiazole；4,7-bis(5-bromothieno[3,2-b]thiophen-2-yl)-5,6-dioctoxy-2,1,3-benzoxadiazole
• CAS: 1443210-54-5
• 化学式: C₃₄H₃₈Br₂N₂O₃S₄
• 分子量: 810.759
• InChiKey: AXUGFTCNQXDRQD-UHFFFAOYSA-N

物化性质

• 沸点：
  775.3±70.0 °C(Predicted)
• 密度：
  1.445±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.9
• 重原子数：
  45
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  噻吩并[3,2-b]噻吩 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 、 溶剂黄146 为溶剂， 反应 94.0h， 生成 4,7-bis(5-bromothieno [3,2-b]thiophen-2-yl)-5,6-bis(octyloxy)benzo[c][1,2,5]oxadiazole
  参考文献：
  名称：

  含苯的可加工2,1,3-苯并恶二唑聚合物的溶液的光学和电化学性质的研究

  摘要：

  四种新型可溶液处理的含苯并恶二唑的交替共聚物，即聚（5,6-双（辛氧基）-4-（5-苯基噻吩-2-基）-7-（噻吩-2-基）苯并[c] [1,2， 5]恶二唑）PBOTPh，聚（5,6-双（辛氧基）-4-（5-苯基硒代-2-基）-7-（硒代-2-基）苯并[c] [1,2,5]恶二唑）PBOSPh，聚（4-（呋喃-2-基）-5,6-双（辛氧基）-7-（5-苯基呋喃-2-基）苯并[c] [1,2,5]恶二唑）PBOFPh和聚（5,6-双（辛氧基）-4-（5-苯基噻吩并[3,2-b]噻吩-2-基）-7-（噻吩并[3,2-b]噻吩-2-基）苯并[通过Suzuki缩聚反应合成了以5,6-双（辛氧基）苯并[c] [1,2,5]恶二唑为受体部分和以苯为供体部分的c] [1,2,5]恶二唑）PBOTTPh。各种电子给体部分被用作聚合物主链中的π桥，以调节聚合物的光电性能。

  DOI：

  10.1149/1945-7111/abab23

文献信息

• 2,1,3-Benzooxadiazole, thiophene and benzodithiophene based random copolymers for organic photovoltaics: thiophene versus thieno[3,2-b]thiophene as π-conjugated linkers
  作者：Seza Goker、Gonul Hizalan、Ece Aktas、Seda Kutkan、Ali Cirpan、Levent Toppare

  DOI：10.1039/c6nj02469f

  日期：——

  conjugated random copolymers comprising benzodithiophene and thiophene as the donor units and benzooxadiazole as the acceptor unit, spaced with thiophene and thieno[3,2-b]thiophene π-bridges, were designed and synthesized. The effects of different linkers on the optical and electrochemical properties were investigated. The polymer containing a thieno[3,2-b]thiophene π-bridge revealed a red shifted absorption

  设计并合成了三种以苯并二噻吩和噻吩为供体单元，苯并恶二唑为受体单元并与噻吩和噻吩并[3,2 - b ]噻吩π-桥隔开的共轭无规共聚物。研究了不同接头对光学和电化学性质的影响。与噻吩类似物相比，含有噻吩并[3,2 - b ]噻吩π桥的聚合物显示出红移的吸收。研究了聚合物：富勒烯共混膜的形貌和光电性能。一种无规共聚物（P 2）与PC 71 BM（[6,6]-苯基-C 71-丁酸甲酯）由于高的短路电流密度和填充因子而显示出5.17％的光伏性能。
• Control of molecular curvature and crystallinity of quinacridone-benzoxadiazole copolymers using different π bridge for polymer solar cells
  作者：Min-Hee Choi、Hyo Yeol Kim、Eui Jin Lee、Doo Kyung Moon

  DOI：10.1016/j.polymer.2016.03.062

  日期：2016.5

  the polymer backbone and crystallinity, especially regarding packing orientation. PQcOx-T exhibits a zigzag conformation with a dihedral angle over 25° and shows an edge-on structure in pristine film. However, PQcOx-TT exhibits a linear conformation with a dihedral angle under 7° and shows crystallized domains and oriented morphology with shoulder peaks in the UV–vis spectra of both solution and film

  通过Suzuki偶联反应获得三种含有不同间隔基（PQcOx-T，PQcOx-TT和PQcOx-biT）的喹ac啶酮-苯并二唑聚合物，以控制聚合物主链的能级和曲率。我们发现聚合物主链和结晶度之间的结构关系，特别是关于堆积方向。PQcOx-T呈现锯齿状构型，二面角超过25°，并且在原始薄膜中显示边缘结构。但是，PQcOx-TT呈线性构型，二面角在7°以下，并且在溶液和薄膜状态的UV-vis光谱中均显示出晶域和定向形态，并具有肩峰。尽管PQcOx-biT表现出线性构象，但其基态和激发态的电子分布都位于受体单元上。所以，PQcOx-biT中的分子内电荷转移（ICT）效果不佳。线性聚合物更喜欢薄膜状态的规则和结晶域，并导致更有效的有机光伏（OPV）器件。PQcOx-TT的PCE值高达3.4％。此外，当我们制造倒装器件时，由于其在有源层和MoO之间的表面电势较小，PCE增至3.6％3。聚合物的堆积方向
• Thieno[3,2-<i>b</i>]thiophene-Bridged D−π–A Polymer Semiconductor Based on Benzo[1,2-<i>b</i>:4,5-<i>b</i>′]dithiophene and Benzoxadiazole
  作者：Xiaochen Wang、Pei Jiang、Yu Chen、Hao Luo、Zhiguo Zhang、Haiqiao Wang、Xiaoyu Li、Gui Yu、Yongfang Li

  DOI：10.1021/ma4005555

  日期：2013.6.25

  Thieno[3,2-b]thiophene-bridged polymer semiconductor, P(BDT-TT-BO), featuring benzoxadiazole (BO) acceptor unit was designed and synthesized. P(BDT-TT-BO) showed broad absorption, in the wavelength range of 350-700 nm, and low highest occupied molecular orbital (HOMO) energy level (-5.31 eV). The benzoxadiazole-based polymer semiconductor exhibited very promising optoelectronic performance. Power conversion efficiency of the polymer solar cell with P(BDT-TT-BO) as donor reached 7.05%, which is the champion efficiency in benzoxadiazole containing conjugated polymers and comparable to that of the most efficient benzothiadiazole-based donor polymers. The sensitive dependence of carrier mobility on the annealing temperature of the polymer semiconductors was systematic studied. After annealing at 200 degrees C, P(BDT-TT-BO)-based polymer field effect transistor showed a mobility of more than 12 times that of unannealed devices, reached 0.023 cm(2) V-1 s(-1), with a high on/off current ratio of 2.7 x 10(5).
• Investigation of Optical and Electrochemical Properties of Benzene Based Solution Processable 2,1,3-Benzooxadiazole Comprising Polymers
  作者：Seza Goker、Gonul Hizalan、Serife O. Hacioglu、Levent Toppare

  DOI：10.1149/1945-7111/abab23

  日期：——

  5]oxadiazole as the acceptor moiety and benzene as the donor moiety were synthesized via Suzuki polycondensation reaction. Various electron donor moieties were used as π bridges in the polymer backbone to tailor the optoelectronic properties of the polymers. To explore the electrochemical and electrochromic properties and the photovoltaic properties of the copolymers, c...

  四种新型可溶液处理的含苯并恶二唑的交替共聚物，即聚（5,6-双（辛氧基）-4-（5-苯基噻吩-2-基）-7-（噻吩-2-基）苯并[c] [1,2， 5]恶二唑）PBOTPh，聚（5,6-双（辛氧基）-4-（5-苯基硒代-2-基）-7-（硒代-2-基）苯并[c] [1,2,5]恶二唑）PBOSPh，聚（4-（呋喃-2-基）-5,6-双（辛氧基）-7-（5-苯基呋喃-2-基）苯并[c] [1,2,5]恶二唑）PBOFPh和聚（5,6-双（辛氧基）-4-（5-苯基噻吩并[3,2-b]噻吩-2-基）-7-（噻吩并[3,2-b]噻吩-2-基）苯并[通过Suzuki缩聚反应合成了以5,6-双（辛氧基）苯并[c] [1,2,5]恶二唑为受体部分和以苯为供体部分的c] [1,2,5]恶二唑）PBOTTPh。各种电子给体部分被用作聚合物主链中的π桥，以调节聚合物的光电性能。