4,7-双（5-溴噻吩-2-基）-5,6-双（辛氧基）苯并[c][1,2,5]恶二唑 | 1314801-37-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 中文名称: 4,7-双（5-溴噻吩-2-基）-5,6-双（辛氧基）苯并[c][1,2,5]恶二唑
• 英文名称: 4,7-bis(5-bromothiophen-2-yl)-5,6-bis(octyloxy)benzo[c][1,2,5]oxadiazole
• 英文别名: 4,7-Bis(5-bromothiophen-2-yl)-5,6-bis(octyloxy)benzo[c][1,2,5] oxadiazole；4,7-bis(5-bromothiophen-2-yl)-5,6-dioctoxy-2,1,3-benzoxadiazole
• CAS: 1314801-37-0
• 化学式: C₃₀H₃₈Br₂N₂O₃S₂
• 分子量: 698.583
• InChiKey: YTEXMHBTLUADJK-UHFFFAOYSA-N

物化性质

• 沸点：
  635.4±65.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  39
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,2-二(辛氧基)苯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 四丁基溴化铵 、 溴 、 硝酸 、 溶剂黄146 、 三(邻甲基苯基)磷 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 185.0h， 生成 4,7-双（5-溴噻吩-2-基）-5,6-双（辛氧基）苯并[c][1,2,5]恶二唑
  参考文献：
  名称：

  Triisopropylsilylethynyl substituted benzodithiophene copolymers: synthesis, properties and photovoltaic characterization

  摘要：

  我们在这里展示了一种简便的方法合成三异丙基硅基乙炔基（TIPS）功能化苯并[1,2-b:4,5-b′]二硫苯（BDT），用于高效的聚合物太阳能电池。

  DOI：

  10.1039/c4tc02107j

文献信息

• Synthesis, characterization, and photovoltaic properties of a low-bandgap copolymer based on 2,1,3-benzooxadiazole
  作者：Jian-Ming Jiang、Po-An Yang、Hsiu-Cheng Chen、Kung-Hwa Wei

  DOI：10.1039/c1cc12040a

  日期：——

  PBDTBO, a conjugated polymer comprising benzo[1,2-b:4,5-b']dithiophene (BDT) and 5,6-bis(octyloxy)benzo[c][1,2,5]oxadiazole (BO) units, exhibits a deep HOMO energy level of -5.27 eV and excellent solubility. A device incorporating PBDTBO and [6,6]-phenyl-C(61)-butyric acid methyl ester (1:1, w/w) exhibited a power conversion efficiency of 5.7%.

  PBDTBO，一种包含苯并[1,2-b：4,5-b']二噻吩（BDT）和5,6-双（辛氧基）苯并[c] [1,2,5]恶二唑（BO）单元的共轭聚合物表现出-5.27 eV的深HOMO能级和出色的溶解度。结合了PBDTBO和[6,6]-苯基-C（61）-丁酸甲酯（1：1，w / w）的装置显示了5.7％的功率转换效率。
• Highly efficient polymer solar cells based on poly(carbazole-alt-thiophene-benzofurazan)
  作者：Bin Zhang、Xiaowen Hu、Minquan Wang、Huiping Xiao、Xiong Gong、Wei Yang、Yong Cao

  DOI：10.1039/c2nj40309a

  日期：——

  An octyloxy substituted benzofurazan based poly(carbazole-alt-thiophene-benzofurazan) (PCzDTBF) was synthesized by Suzuki polycondensation. The absorption spectra of the polymer were peaked at 385 and 540 nm, and the HOMO and LUMO energy levels were −5.34 and −3.46 eV, respectively. The hole mobility was found to be 4.8 × 10−4 cm2 V−1 S−1 by the space charge limited current (SCLC) method, and the surface energy (Es) was calculated to be 35.8 mJ m−2 from the contact-angle measurement. Polymer solar cells (PSCs) based on the blend of PCzDTBF and PCBM with a weight ratio of 1 : 2 were fabricated. The devices were found to have a power conversion efficiency (PCE) of 4.2% in the device configuration of ITO/PSS:PEDOT/PCzDTBF:PC70BM/Al. By utilizing poly[(9,9-dioctyl-2,7-fluorene)-alt-(9,9-bis(3′-(N,N-dimethylamino)propyl)-2,7-fluorene)] (PFN) as the cathode interfacial layer, the PCE was enhanced to 5.48%, with an open-circuit voltage (Voc) of 0.90 V, a short-circuit current density (Jsc) of 7.73 mA cm−2, and a fill factor (FF) of 67%. The high efficiencies could be ascribed to the good morphology, resulting from the matched surface energies of the PCzDTBF and PCBM components, and the distinct enhancement on Voc and FF by the PFN layer, where it is possible that a built-in field potential exists between the active layer and cathode.

  通过铃木聚合偶联反应合成了一种基于辛氧基取代苯并呋咱的聚(咔唑-alt-噻吩-苯并呋咱)(PCzDTBF)。该聚合物的吸收光谱在385和540 nm处有峰，最高占据分子轨道(HOMO)和最低未占据分子轨道(LUMO)能级分别为−5.34和−3.46 eV。通过空间电荷限制电流(SCLC)法测得空穴迁移率为4.8 × 10−4 cm² V⁻¹ S⁻¹，通过接触角测量计算得出表面能(Es)为35.8 mJ m⁻²。基于PCzDTBF和PCBM以1:2的质量比例混合制备了聚合物太阳能电池(PSCs)。在ITO/PSS:PEDOT/PCzDTBF:PC70BM/Al的器件结构中，器件的功率转换效率(PCE)为4.2%。利用聚[(9,9-二辛基-2,7-芴)-alt-(9,9-双(3′-(N,N-二甲基氨基)丙基)-2,7-芴)](PFN)作为阴极界面层，PCE提升至5.48%，开路电压(Voc)为0.90 V，短路电流密度(Jsc)为7.73 mA cm⁻²，填充因子(FF)为67%。高效率可归因于PCzDTBF和PCBM组分之间匹配的表面能导致的良好形态，以及PFN层对Voc和FF的显著增强作用，可能是在活性层和阴极之间存在内置场电位。
• 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。
• 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