2,6-dibromo-8-hexylbithieno[3,2-b:2',3'-e]pyridine | 483334-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,6-dibromo-8-hexylbithieno[3,2-b:2',3'-e]pyridine
• 英文别名: 5,11-Dibromo-8-hexyl-6,10-dithia-2-azatricyclo[7.3.0.03,7]dodeca-1,3(7),4,8,11-pentaene
• CAS: 483334-35-6
• 化学式: C₁₅H₁₅Br₂NS₂
• 分子量: 433.231
• InChiKey: IBMZYJVZHXBJDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  8-hexylbithieno[3,2-b:2',3'-e]pyridine 在 正丁基锂 、 三甲基氯化锡 、 N-溴代丁二酰亚胺(NBS) 作用下， 以26%的产率得到2,6-dibromo-8-hexylbithieno[3,2-b:2',3'-e]pyridine
  参考文献：
  名称：

  Polycyclic Aromatics with Flanking Thiophenes: Tuning Energy Level and Band Gap of Conjugated Polymers for Bulk Heterojunction Photovoltaics

  摘要：

  In the pursuit of donor-acceptor low band gap polymers for photovoltaic applications, finding an optimal donor monomer which maximizes the photovoltaic efficiency is it complex synthetic optimization problem. We synthesized three different bithiophenes flanking a center aromatic ring (pyrrole, benzene, or pyridine) as the donor monomers (DTPr, DTBn, and DTPn) with decreasing electron-donating ability. An array of six electrochemically and Optically unique polymers were prepared by copolymerizing these three monomers with 2,1,3-benzothiadiazole and with thiophene. The optical, electronic, and photovoltaic properties of these polymers were investigated. Among this series, we Found that the HOMO energy level of the polymer is dominated by the most electron-rich ring in the polymer backbone. The optical band gap, conversely, involves the entire polymeric system. Among the three donor monomers investigated, we identified that DTBn-based polymers exhibited the most potential in photovoltaic applications due to their moderately low band gaps and low HOMO energy levels.

  DOI：

  10.1021/ma902164q

文献信息

• 4-Hexylbithieno[3,2-<i>b</i>:2‘3‘-<i>e</i>]pyridine:  An Efficient Electron-Accepting Unit in Fluorene and Indenofluorene Copolymers for Light-Emitting Devices
  作者：Prashant Sonar、Jingying Zhang、Andrew C. Grimsdale、Klaus Müllen、Mathieu Surin、Roberto Lazzaroni、Philippe Leclère、Steve Tierney、Martin Heeney、Iain McCulloch

  DOI：10.1021/ma035329u

  日期：2004.2.1

  4-Hexylbithienopyridine has been prepared as a novel electron-accepting monomer for conjugated polymers. To test its electronic properties, alternating copolymers with fluorene and indenofluorene polymers have been prepared. The copolymers displayed reduction potentials about 0.5 V lower than for the corresponding fluorene and indenofluorene homopolymers, indicating much improved electron-accepting properties. Analysis of the microscopic morphology of thin films of the copolymers by AFM shows that they lack the extensive supramolecular order seen with the homopolymers, which is attributed to the bithienopyridine units disrupting the pi-stacking. LEDs using these polymers as the emitting layer produce blue-green emission with low turn-on voltages with aluminum electrodes confirming their improved electron affinity. The indenofluorene copolymer displayed an irreversible red shift in emission at high voltages, which is attributed to oxidation of the indenofluorene units. This red shift occurred at higher potentials than for indenofluorene homopolymers in LEDs, suggesting that the heterocyclic moieties offer some protection against electrically promoted oxidation.
• Polycyclic Aromatics with Flanking Thiophenes: Tuning Energy Level and Band Gap of Conjugated Polymers for Bulk Heterojunction Photovoltaics
  作者：Samuel C. Price、Andrew C. Stuart、Wei You

  DOI：10.1021/ma902164q

  日期：2010.1.26

  In the pursuit of donor-acceptor low band gap polymers for photovoltaic applications, finding an optimal donor monomer which maximizes the photovoltaic efficiency is it complex synthetic optimization problem. We synthesized three different bithiophenes flanking a center aromatic ring (pyrrole, benzene, or pyridine) as the donor monomers (DTPr, DTBn, and DTPn) with decreasing electron-donating ability. An array of six electrochemically and Optically unique polymers were prepared by copolymerizing these three monomers with 2,1,3-benzothiadiazole and with thiophene. The optical, electronic, and photovoltaic properties of these polymers were investigated. Among this series, we Found that the HOMO energy level of the polymer is dominated by the most electron-rich ring in the polymer backbone. The optical band gap, conversely, involves the entire polymeric system. Among the three donor monomers investigated, we identified that DTBn-based polymers exhibited the most potential in photovoltaic applications due to their moderately low band gaps and low HOMO energy levels.