2,7-divinyl-9,9-di-n-octylfluorene | 360068-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,7-divinyl-9,9-di-n-octylfluorene
• 英文别名: 2,7-Divinyl-9,9-dioctylfluorene；2,7-bis(ethenyl)-9,9-dioctylfluorene
• CAS: 360068-34-4
• 化学式: C₃₃H₄₆
• 分子量: 442.728
• InChiKey: BUIGXSGVFMLUBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  566.5±40.0 °C(Predicted)
• 密度：
  0.938±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  33
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2,7-二碘芴 在 四(三苯基膦)钯 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.08h， 生成 2,7-divinyl-9,9-di-n-octylfluorene
  参考文献：
  名称：

  Synthesis of π-Bridged Dually-Dopable Conjugated Polymers from Benzimidazole and Fluorene: Separating Sterics from Electronics

  摘要：

  We describe the synthesis and characterization of three new alternating copolymers containing fluorene and a dually dopable benzimidazole moiety. Poly(2-n-heptyl-benzimidazole-alt-9,9-di-n-octylfluorene) (PBIF), poly(2-n-heptyl-benzimidazole-vinylene-9,9-di-n-octylfluorene) (PBIF-VL), and poly(2-n-heptyl-benzimidazole-ethynylene-9,9-di-n-octyl-fluorene) (PBIF-EL) were synthesized from Suzuki, Heck, and Sonogashira cross-coupling reactions in reasonable yield. The materials were characterized through ultraviolet-visible spectroscopy, photoluminescence, and cyclic voltammetry. The vinyl and ethynyl bridges in PBIF-VL and PBIF-EL were incorporated to separate benzimidazole and fluorene units while retaining conjugation. This allowed us to differentiate between steric and electronic contributions to the band gap (E-g) changes that occur upon acid/base doping of these materials. We demonstrate that the blue shift arising from acid doping PBIF is due to steric torsion, while the red shift found upon base doping PBIF is due to both sterics and possibly an electronic effect. These findings are supported through the use of molecular modeling.

  DOI：

  10.1021/acs.macromol.5b01174

文献信息

• A low band gap donor–acceptor copolymer containing fluorene and benzothiadiazole units: synthesis and photovoltaic properties
  作者：Jianing Pei、Shanpeng Wen、Yinhua Zhou、Qingfeng Dong、Zhaoyang Liu、Jibo Zhang、Wenjing Tian

  DOI：10.1039/c0nj00378f

  日期：——

  A new low band gap copolymer containing dialkylfluorene and 4,7-dithienyl-2,1,3-benzothiadiazole (TBT), poly(fluorenevinylene-alt-4,7-dithienyl-2,1,3-benzothiadiazole) (PF-TBT) was synthesized by Heck cross-coupling polymerization. The copolymer is soluble in common organic solvents such as chloroform, tetrahydrofuran and chlorobenzene. The TGA result indicated that the copolymer possesses good thermal

  一种新的低带隙共聚物，其中含有二烷基芴和 4,7-二噻吩基-2,1,3-苯并噻二唑（TBT），通过Heck交叉偶联聚合合成了聚（芴撑-乙烯-alt-4,7-二噻吩基-2,1,3-苯并噻二唑）（PF-TBT）。该共聚物可溶于常见的有机溶剂，例如氯仿， 四氢呋喃 和 氯苯。TGA结果表明该共聚物具有良好的热稳定性。研究了PF-TBT的吸收，电化学和光电性能，并与结构类似于PF-的聚（芴乙烯-alt-4,7-二苯基-2,1,3-苯并噻二唑）（PF-DBT）进行了比较。技术性贸易壁垒。该共聚物表现出宽的吸收带，其吸收边缘接近700nm，并且光学带隙为1.82eV。循环伏安法研究表明，较低的HOMO能级可确保较高的开路电压（V oc）当PF-TBT用作光伏电池中的施主材料时。使用PF-TBT作为施主，[6,6]-苯基C61丁酸甲酯（PCBM）作为受主的体异质结（BHJ）太阳能电池：ITO / PEDOT的结构：PSS
• Synthesis of Conjugated Copolymer Containing Spirobifluorene Skeleton by Acyclic Diene Metathesis Polymerization for Polymer Light‐Emitting Diode Applications
  作者：Seongwook Park、Soyeong Jeong、Changmuk Kang、Sukwon Hong

  DOI：10.1002/bkcs.12281

  日期：2021.6

  metathesis (ADMET) polymerization of 2,7-divinyl-9,9-di-n-octylfluorene (DVF). Additionally, various ratios of DVF and 2,2′,7,7′-tetravinyl-9,9′-spirobifluorene (TVSF) were subjected to ADMET polymerization to obtain polymers P1–P7. Polymers P1–P4 were analyzed with gel permeation chromatography, UV–vis spectroscopy, and photoluminescence spectroscopy. As the TVSF ratio increases, polymers exhibit lower

  Grubbs 型、Hoveyda 型、环状烷基氨基卡宾 (CAAC) 基钌烯烃复分解催化剂用于 2,7-二乙烯基-9,9-二-n的无环二烯复分解 (ADMET) 聚合-辛基芴（DVF）。此外，将不同比例的 DVF 和 2,2',7,7'-四乙烯基-9,9'-螺二芴（TVSF）进行 ADMET 聚合以获得聚合物 P1-P7。聚合物 P1-P4 用凝胶渗透色谱、紫外-可见光谱和光致发光光谱分析。随着 TVSF 比率的增加，聚合物表现出较低的溶解度，但在光致发光光谱中的带更窄。聚合物发光二极管 (PLED) 器件由聚合物 P1、P2 和 P3 制成。PLED 器件的性能表明，包含更多螺二芴嵌段的聚合物显示出更好的开启电压、亮度、电流效率和功率效率。
• D-π-A Dye Sensitizers Made of Polymeric Metal Complexes Containing 1,10-Phenanthroline and Alkylfluorene or Alkoxybenzene: Synthesis, Characterization and Photovoltaic Performance for Dye-Sensitized Solar Cells
  作者：Xiaoguang Yu、Xueliang Jin、Guipeng Tang、Jun Zhou、Wei Zhang、Dahai Peng、Jiaomei Hu、Chaofan Zhong

  DOI：10.1002/ejoc.201300192

  日期：2013.9

  developed for dye-sensitized solar cell applications. The target dyes use alkoxybenzene or alkylfluorene as the electron donor, a C=C moiety as the π linker, and the phenanthroline derivative complex was used as the electron acceptor. Bipyridine derivatives were ancillary ligands as well as providing anchoring groups. The thermal, photophysical, electrochemical and photovoltaic properties of these copolymers

  四种基于 1,10-菲咯啉金属配合物和烷基芴或烷氧基苯的聚合物金属配合物 (P1-P4) 通过 Heck 偶联反应合成，并被开发用于染料敏化太阳能电池应用。目标染料使用烷氧基苯或烷基芴作为电子供体，C=C部分作为π连接基团，菲咯啉衍生物络合物作为电子受体。联吡啶衍生物是辅助配体并提供锚定基团。通过热重分析 (TGA)、差示扫描量热法 (DSC)、C-V 曲线和 I-V 曲线研究了这些共聚物的热、光物理、电化学和光伏性能。使用这些聚合物金属络合物作为染料敏化剂的染料敏化太阳能电池表现出相当大的功率转换效率 (PCE)。含有烷氧基苯的染料 (P3, P4) 的 PCE 值高于相应的含有烷基芴的目标聚合物 (P1, P2)，染料 P3 的最大功率转换效率为 2.12 % (Jsc = 4.91 mA/cm2, Voc = 0.69 V , FF = 62.5)。此外，四种聚合物均具有优异的稳定性，其热分解温度均超过
• Synthesis of π-Bridged Dually-Dopable Conjugated Polymers from Benzimidazole and Fluorene: Separating Sterics from Electronics
  作者：Jared D. Harris、Jiakai Liu、Kenneth R. Carter

  DOI：10.1021/acs.macromol.5b01174

  日期：2015.10.13

  We describe the synthesis and characterization of three new alternating copolymers containing fluorene and a dually dopable benzimidazole moiety. Poly(2-n-heptyl-benzimidazole-alt-9,9-di-n-octylfluorene) (PBIF), poly(2-n-heptyl-benzimidazole-vinylene-9,9-di-n-octylfluorene) (PBIF-VL), and poly(2-n-heptyl-benzimidazole-ethynylene-9,9-di-n-octyl-fluorene) (PBIF-EL) were synthesized from Suzuki, Heck, and Sonogashira cross-coupling reactions in reasonable yield. The materials were characterized through ultraviolet-visible spectroscopy, photoluminescence, and cyclic voltammetry. The vinyl and ethynyl bridges in PBIF-VL and PBIF-EL were incorporated to separate benzimidazole and fluorene units while retaining conjugation. This allowed us to differentiate between steric and electronic contributions to the band gap (E-g) changes that occur upon acid/base doping of these materials. We demonstrate that the blue shift arising from acid doping PBIF is due to steric torsion, while the red shift found upon base doping PBIF is due to both sterics and possibly an electronic effect. These findings are supported through the use of molecular modeling.