2,6-dibromo-8-(1-hexylnonyl)dithieno[3,2-b:2',3'-e]pyridine | 1206898-78-3

• 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-(1-hexylnonyl)dithieno[3,2-b:2',3'-e]pyridine
• 英文别名: 5,11-Dibromo-8-pentadecan-7-yl-6,10-dithia-2-azatricyclo[7.3.0.03,7]dodeca-1,3(7),4,8,11-pentaene；5,11-dibromo-8-pentadecan-7-yl-6,10-dithia-2-azatricyclo[7.3.0.03,7]dodeca-1,3(7),4,8,11-pentaene
• CAS: 1206898-78-3
• 化学式: C₂₄H₃₃Br₂NS₂
• 分子量: 559.473
• InChiKey: VAWFOKPMIWCQCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  2-溴-4-(N-叔丁氧羰基胺基)噻吩 、 2-hexyldecanal 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到2,6-dibromo-8-(1-hexylnonyl)dithieno[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

• 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.