5,6-bis(decyloxy)naphtho[2,1-b:3,4-b']dithiophene | 1394292-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 5,6-bis(decyloxy)naphtho[2,1-b:3,4-b']dithiophene
• 英文别名: 5,6-didecyloxynaphtho[2,1-b:3,4-b']dithiophene；14,15-Didecoxy-5,8-dithiatetracyclo[10.4.0.02,6.07,11]hexadeca-1(16),2(6),3,7(11),9,12,14-heptaene
• CAS: 1394292-27-3
• 化学式: C₃₄H₄₈O₂S₂
• 分子量: 552.886
• InChiKey: XGRFLRVLEMJMEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.3
• 重原子数：
  38
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-bis(decyloxy)naphtho[2,1-b:3,4-b']dithiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到2,9-dibromo-5,6-didecyloxynaphtho[2,1-b:3,4-b']dithiophene
  参考文献：
  名称：

  新型蝶形熔融杂并乙炔：溶液处理的场效应晶体管的合成，性质和器件性能

  摘要：

  通过在不同溶剂naphthodithiophene的溴化得到的两个四溴化中间体被用来构建新的高度π扩展蝶形杂芳烃1 - 6，含有任一种8位或10的稠环。基于化合物1的溶液处理的有机场效应晶体管展现出令人鼓舞的器件性能，其在环境大气下的空穴迁移率为0.072 cm 2 V –1 s –1，电流开/关比为10 6。

  DOI：

  10.1021/ol301852m

文献信息

• Dye-sensitized solar cells based on organic dyes with naphtho[2,1-b:3,4-b′]dithiophene as the conjugated linker
  作者：Xiaoxu Wang、Lei Guo、Ping Fang Xia、Fan Zheng、Man Shing Wong、Zhengtao Zhu

  DOI：10.1039/c3ta12901b

  日期：——

  Naphtho[2,1-b:3,4-b′]dithiophene is used for the first time as the π-spacer for metal-free organic dyes in dye-sensitized solar cells (DSSCs). Four new donor–(π-spacer)–acceptor organic dyes using triarylamine or carbazole as the electron-donating group, cyanoacrylic acid as the electron-withdrawing anchoring moiety, and naphtho[2,1-b:3,4-b′]dithiophene as the linker were synthesized. The absorption, electrochemical, and photovoltaic properties of the dyes were investigated. DSSCs based on these dyes as sensitizers had efficiencies ranging from 3.98% to 4.60%. The highest efficiency was 4.60 ± 0.16% with a Jsc of 10.8 ± 0.4 mA cm−2, a Voc of 657 ± 5 mV, and a fill factor of 64.0 ± 0.2% under 100 mW AM 1.5 irradiation. The incident photon-to-current efficiency (IPCE) measurement showed that these dyes had high quantum efficiency over the visible range, and the long π-spacer of the molecule resulted in broader IPCE at long wavelength and high Jsc. Photovoltage transient was used to understand the electron recombination and the trends of the photovoltaic parameters (e.g. Voc and efficiency) of the DSSCs based on these organic dyes.

  首次采用萘并[2,1-b:3,4-b']二噻吩作为染料敏化太阳能电池（DSSCs）中不含金属有机染料的π-桥连单元。合成了四种新型供体-（π-桥连单元）-受体有机染料，分别使用三芳胺或咔唑作为电子供体基团，氰基丙烯酸作为电子吸引锚定部分，萘并[2,1-b:3,4-b']二噻吩作为连接单元。研究了这些染料的吸收、电化学和光伏特性。基于这些染料作为敏化剂的DSSCs效率范围从3.98%到4.60%。在100 mW AM 1.5辐照下，最高效率为4.60 ± 0.16%，对应的Jsc为10.8 ± 0.4 mA cm⁻²，Voc为657 ± 5 mV，填充因子为64.0 ± 0.2%。入射光子-电流效率（IPCE）测量显示，这些染料在可见光区域具有高量子效率，分子的长π-桥连单元导致在长波长处IPCE更宽，Jsc更高。使用光电压瞬态来理解基于这些有机染料的DSSCs的电子复合和光伏参数（如Voc和效率）的趋势。