1,4-dibromo-2,5-bis[2-(tert-butyldimethylsilanyloxy)ethyl]benzene | 1201908-84-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-dibromo-2,5-bis[2-(tert-butyldimethylsilanyloxy)ethyl]benzene
• 英文别名: (2,2'-(2,5-dibromo-1,4-phenylene)bis(ethane-2,1-diyl))bis(oxy)bis(tert-butyldimethylsilane)；2,5-bis(2-(tert-butyldimethylsilyloxy)ethyl)-1,4-benzene dibromide；Tert-butyl-[2-[2,5-dibromo-4-[2-[tert-butyl(dimethyl)silyl]oxyethyl]phenyl]ethoxy]-dimethylsilane
• CAS: 1201908-84-0
• 化学式: C₂₂H₄₀Br₂O₂Si₂
• 分子量: 552.537
• InChiKey: ABQPURREPOGNQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.34
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-dibromo-2,5-bis[2-(tert-butyldimethylsilanyloxy)ethyl]benzene 在 四(三苯基膦)钯 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 48.0h， 生成 2-{2,5-bis[2-(tert-butyldimethylsilanyloxy)ethyl]-4-pyridin-2-ylphenyl}-5-bromopyridine
  参考文献：
  名称：

  Pyridinium salt-based molecules as cathode interlayers for enhanced performance in polymer solar cells

  摘要：

  成功合成了一系列基于缺电子吡啶鎓盐的水/醇溶性小分子，即 BTPS、BnPS 和 F8PS。对它们的光物理和电化学性质进行了深入研究。由于 F8PS 具有良好的成膜能力，因此被用作有机光伏电池的阴极中间膜。与基于裸铝阴极的装置相比，开路电压（Voc）、短路电流密度（Jsc）和填充因子（FF）同时得到了提高，功率转换效率（PCE）从 4.32% 提高到 6.56%。Voc 从 0.76 V 显著提高到 0.94 V，这是迄今为止文献报道的基于聚[N-9′-十七烷基-2,7-咔唑-alt-5,5-(4′,7′-二-2-噻吩基-2′,1′,3′-苯并噻二唑)]（PCDTBT）活性层的聚合物太阳能电池（PSCs）的最佳结果之一：[6,6]-苯基-C71-丁酸甲酯（PC71BM）。Voc 值的大幅提高可能是由于 F8PS 产生了界面偶极子。研究还表明，与使用裸铝阴极的器件相比，用乙醇对活性层进行后处理后，器件的整体效率从最初的 4.32% 提高到了 5.55%。因此，吡啶鎓盐沉积后性能的提高可能是由于乙醇处理和吡啶鎓盐薄层存在的综合影响。亲水性吡啶鎓盐衍生物具有良好的水/酒精溶解性、理想的 HOMO/LUMO 能级和出色的电子传递/收集能力，这使它们很有希望成为高效 PSC 的电子传输材料系列。

  DOI：

  10.1039/c3ta01226c
• 作为产物：
  描述：

  2,2'-(2,5-dibromo-1,4-phenylene)diethanol 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以95%的产率得到1,4-dibromo-2,5-bis[2-(tert-butyldimethylsilanyloxy)ethyl]benzene
  参考文献：
  名称：

  Poly(Pyridinium Phenylene)s: Water-Soluble N-Type Polymers

  摘要：

  Poly(pyridinium phenylene) conjugated polymers are synthesized by a cross-coupling and cyclization sequence. These polyelectrolytes are freely soluble in water and display high degrees of electroactivity. When reduced (n-doped) these materials display in situ conductivities as high as 160 S/cm. The high conductivity is attributed to the planar structure that is enforced by the cyclic structures of the polymer. The electron affinities are compared to PCBM, a C(60) based n-type material. We find that these polymers undergo excited state electron transfer reactions with other donor conjugated polymers and hence may find utility in photovoltaic devices.

  DOI：

  10.1021/ja906513u

文献信息

• Poly(3-hexylthiophene)-<i>block</i>-poly(pyridinium phenylene)s: Block Polymers of p- and n-Type Semiconductors
  作者：Daisuke Izuhara、Timothy M. Swager

  DOI：10.1021/ma102566u

  日期：2011.4.26

  Conjugated crystalline-crystalline donor- acceptor-donor block copolymer semiconductors, with regio-regular poly(3-hexylthiophene) as a donor (p-type) block and poly(pyridinium pheneylene) as an acceptor (n-type) block within the backbone, were produced by sequential Grignard metathesis synthesis of poly(3-hexylthiophene), a Yamamoto-type cross-coupling polymerization-cyclization sequence. These conjugated block copolymers are soluble in organic solvents and display broad optical absorption bands extending close to the near-infrared region. They show reversible ambipolar redox properties with high electron affinities of 3.8-4.0 eV as well as useful ionization potentials of 5.1 eV that are characteristic of the respective blocks. Block copolymers from p- and n-type organic semiconductors are of interest for the formation of nanostructured bulk heterojunctions in photovoltaic devices.
• Poly(Pyridinium Phenylene)s: Water-Soluble N-Type Polymers
  作者：Daisuke Izuhara、Timothy M. Swager

  DOI：10.1021/ja906513u

  日期：2009.12.16

  Poly(pyridinium phenylene) conjugated polymers are synthesized by a cross-coupling and cyclization sequence. These polyelectrolytes are freely soluble in water and display high degrees of electroactivity. When reduced (n-doped) these materials display in situ conductivities as high as 160 S/cm. The high conductivity is attributed to the planar structure that is enforced by the cyclic structures of the polymer. The electron affinities are compared to PCBM, a C(60) based n-type material. We find that these polymers undergo excited state electron transfer reactions with other donor conjugated polymers and hence may find utility in photovoltaic devices.
• Pyridinium salt-based molecules as cathode interlayers for enhanced performance in polymer solar cells
  作者：Hua Ye、Xiaowen Hu、Zhixiong Jiang、Dongcheng Chen、Xin Liu、Han Nie、Shi-Jian Su、Xiong Gong、Yong Cao

  DOI：10.1039/c3ta01226c

  日期：——

  A series of water/alcohol-soluble small molecules based on electron-deficient pyridinium salts namely BTPS, BnPS and F8PS were successfully synthesized. Their photophysical and electrochemical properties were thoroughly studied. Due to its good film-forming ability, F8PS was employed as a cathode interlayer in an organic photovoltaic cell. Simultaneous enhancements in open-circuit voltage (Voc), short circuit current density (Jsc) and fill factor (FF) were achieved, and the power conversion efficiency (PCE) was increased from 4.32% to 6.56% compared to the device based on the bare Al cathode. Voc was significantly improved from 0.76 V to 0.94 V, and it is one of the best results reported in literature to date for polymer solar cells (PSCs) based on the active layer of poly [N-9′-heptadecanyl-2,7-carbazole-alt-5,5-(4′,7′- di-2-thienyl-2′,1′,3′-benzothiadiazole)] (PCDTBT):[6,6]-phenyl-C71-butyric acid methylester (PC71BM). The greatly increased Voc may be due to the interface dipoles generated by F8PS. It was also demonstrated that post treatment of the active layer with ethanol gave an improvement of the overall device efficiency from the initial 4.32% to 5.55%, compared to the device with the bare Al cathode. Therefore, the improvement in performance after pyridinium salt deposition may be due to a combination of the effects of ethanol treatment and the presence of the thin pyridinium salt layer. The good water/alcohol solubility, ideal HOMO/LUMO energy levels and the excellent electron transfer/collection ability of the hydrophilic pyridinium salt derivatives makes them a promising family of electron transport materials for highly efficient PSCs.

  成功合成了一系列基于缺电子吡啶鎓盐的水/醇溶性小分子，即 BTPS、BnPS 和 F8PS。对它们的光物理和电化学性质进行了深入研究。由于 F8PS 具有良好的成膜能力，因此被用作有机光伏电池的阴极中间膜。与基于裸铝阴极的装置相比，开路电压（Voc）、短路电流密度（Jsc）和填充因子（FF）同时得到了提高，功率转换效率（PCE）从 4.32% 提高到 6.56%。Voc 从 0.76 V 显著提高到 0.94 V，这是迄今为止文献报道的基于聚[N-9′-十七烷基-2,7-咔唑-alt-5,5-(4′,7′-二-2-噻吩基-2′,1′,3′-苯并噻二唑)]（PCDTBT）活性层的聚合物太阳能电池（PSCs）的最佳结果之一：[6,6]-苯基-C71-丁酸甲酯（PC71BM）。Voc 值的大幅提高可能是由于 F8PS 产生了界面偶极子。研究还表明，与使用裸铝阴极的器件相比，用乙醇对活性层进行后处理后，器件的整体效率从最初的 4.32% 提高到了 5.55%。因此，吡啶鎓盐沉积后性能的提高可能是由于乙醇处理和吡啶鎓盐薄层存在的综合影响。亲水性吡啶鎓盐衍生物具有良好的水/酒精溶解性、理想的 HOMO/LUMO 能级和出色的电子传递/收集能力，这使它们很有希望成为高效 PSC 的电子传输材料系列。