3,6-dibromo-9,9-dioctylfluorene | 443770-34-1

• 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: 3,6-dibromo-9,9-dioctylfluorene
• 英文别名: 3,6-Dibromo-9,9-dioctylfluorene
• CAS: 443770-34-1
• 化学式: C₂₉H₄₀Br₂
• 分子量: 548.445
• InChiKey: WHGVVVSUOKTFQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.98
• 重原子数：
  31.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  3,6-dibromo-9,9-dioctylfluorene 在 盐酸 、 N-氯代丁二酰亚胺 、 溶剂黄146 作用下， 以 氯仿 、 水 为溶剂， 反应 24.0h， 以70%的产率得到3,6-dibromo-2,7-dichloro-9,9-dioctylfluorene
  参考文献：
  名称：

  Synthesis and Supramolecular Assembly of Pentacyclic Dithienofluorene and Diselenophenofluorene Derivatives

  摘要：

  2,7-Diiodo-3,6-dibromofluorene and 2,7-dichloro-3,6-dibromofluorene have been successfully synthesized. The two key intermediates enable us to implement a regioselective Sonogashira reaction followed by intramolecular thiolate/acetylene cyclization, forming two regiospecific pentacyclic dithieno[2,3-b:7,6-b']fluorene (2,7-DTF) and dithieno[3,2-b:6,7-b']fluorene (3,6-DTF) isomeric molecules, respectively. By using a similar strategy, selenophene-based diselenopheno[2,3-b:7,6-b']fluorene (2,7-DSF) as well as diselenopheno[3,2-b:6,7-b'] fluorene (3,6-DSF) were also prepared. The isomeric and sulfur/selenium effects determine the optical, electrochemical, and orbital properties. X-ray crystallography revealed that 2,7-DTF and 3,6-DTF molecules assemble into supramolecular helical structures.

  DOI：

  10.1021/ol4036787
• 作为产物：
  描述：

  3,6-二溴-9-芴酮 在 一水合肼 、 potassium hydroxide 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 二乙二醇 为溶剂， 反应 12.0h， 生成 3,6-dibromo-9,9-dioctylfluorene
  参考文献：
  名称：

  Synthesis and Supramolecular Assembly of Pentacyclic Dithienofluorene and Diselenophenofluorene Derivatives

  摘要：

  2,7-Diiodo-3,6-dibromofluorene and 2,7-dichloro-3,6-dibromofluorene have been successfully synthesized. The two key intermediates enable us to implement a regioselective Sonogashira reaction followed by intramolecular thiolate/acetylene cyclization, forming two regiospecific pentacyclic dithieno[2,3-b:7,6-b']fluorene (2,7-DTF) and dithieno[3,2-b:6,7-b']fluorene (3,6-DTF) isomeric molecules, respectively. By using a similar strategy, selenophene-based diselenopheno[2,3-b:7,6-b']fluorene (2,7-DSF) as well as diselenopheno[3,2-b:6,7-b'] fluorene (3,6-DSF) were also prepared. The isomeric and sulfur/selenium effects determine the optical, electrochemical, and orbital properties. X-ray crystallography revealed that 2,7-DTF and 3,6-DTF molecules assemble into supramolecular helical structures.

  DOI：

  10.1021/ol4036787

文献信息

• Ladder‐Type Nonacyclic Arene Bis(thieno[3,2‐b]thieno)cyclopentafluorene as a Promising Building Block for Non‐Fullerene Acceptors
  作者：Xiaobing Fan、Jianhong Gao、Wei Wang、Shengqiang Xiao、Chun Zhan、Xinhui Lu、Qichun Zhang

  DOI：10.1002/asia.201801669

  日期：2019.5.15

  peripheral acceptor units. The energy level of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of BTTFIC locate at −5.56 and −3.95 eV, respectively, presenting a low optical band gap of 1.58 eV. Encouragingly, polymer solar cells based on the blends of BTTFIC with both the representative wide‐ and low‐bandgap polymer donors (PBDB‐T, 1.82 eV. PTB7‐Th, 1.58 eV)

  梯形非环芳烃（双（噻吩并[3,2-b]噻吩）环戊芴（BTTF））是通过将噻吩并噻吩与芴核从二甲基9,9-二辛基-2,7的合成子中融合而设计和合成的-双（噻吩并[3,2-b]噻吩-2-基）芴3,6-二羧酸酯。以BTTF为主要供体单元，制备了一种新型的受体－供体－受体（A‐D‐A）型非富勒烯小分子受体（BTTFIC），其中1,1-二氰基亚甲基-3-茚满酮（IC）为外围受体单元。BTTFIC的最高占据分子轨道（HOMO）和最低未占据分子轨道（LUMO）的能级分别位于-5.56和-3.95 eV，具有1.58 eV的低光学带隙。令人鼓舞的是，基于BTTFIC混合物的聚合物太阳能电池具有代表性的宽带隙和低带隙聚合物供体（PBDB-T，1.82 eV。PTB7-Th，1.58 eV）提供超过8％的功率转换效率（PBDB-T：BTTFIC为8.78±0.18％和8.18±0.29％对于PTB7-Th：B
• Side-chain modulation of dithienofluorene-based copolymers to achieve high field-effect mobilities
  作者：Chia-Hao Lee、Yu-Ying Lai、Jhih-Yang Hsu、Po-Kai Huang、Yen-Ju Cheng

  DOI：10.1039/c6sc04129a

  日期：——

  2-octyldodecyl (R2) side chains shows a less ordered amorphous character. The OFET device using PDTFDPP20 with a face-on orientation determined by GIXS measurements achieved a high hole-mobility of up to 5 cm2 V−1 s−1. The high rigidity and coplanarity of the DTF motifs play an important role in facilitating intramolecular 1-dimensional charge transport within the polymer backbones. The implementation

  开发了梯型二噻吩并[3,2- b：6,7- b ']芴（DTF），其中中心芴在其2,3-和6,7连接处与两个外部噻吩环稠合。将五环DTF单体与二噻吩并二酮基吡咯并吡咯（DPP）受体聚合，得到三种交替的供体-受体共聚物PDTFDPP16，PDTFDPP20和PDTFDPP32，它们掺入了不同的脂族侧链（DTF处为R 1基团，DPP部分为R 2基团）。聚合物中的侧链变化不仅在确定固有分子性质方面而且在确定分子间堆积方面都起着重要作用。正如二维GIXS测量所证明的那样，PDTFDPP16与辛基（R 1）和2-乙基己基（R 2）侧链趋于对准在边缘上的π堆叠方向，而PDTFDPP20使用2-丁基辛基（R 1）和2-乙基己基（R 2）采用主要是面对面的方向。具有最大的2-丁基辛基（R 1）和2-辛基十二烷基（R 2）侧链的PDTFDPP32显示出较少的无定形特征。使用OFET器件PDTFDPP20具有
• Synthesis and Supramolecular Assembly of Pentacyclic Dithienofluorene and Diselenophenofluorene Derivatives
  作者：Chia-Hao Lee、Yu-Ying Lai、Sheng-Wen Cheng、Yen-Ju Cheng

  DOI：10.1021/ol4036787

  日期：2014.2.7

  2,7-Diiodo-3,6-dibromofluorene and 2,7-dichloro-3,6-dibromofluorene have been successfully synthesized. The two key intermediates enable us to implement a regioselective Sonogashira reaction followed by intramolecular thiolate/acetylene cyclization, forming two regiospecific pentacyclic dithieno[2,3-b:7,6-b']fluorene (2,7-DTF) and dithieno[3,2-b:6,7-b']fluorene (3,6-DTF) isomeric molecules, respectively. By using a similar strategy, selenophene-based diselenopheno[2,3-b:7,6-b']fluorene (2,7-DSF) as well as diselenopheno[3,2-b:6,7-b'] fluorene (3,6-DSF) were also prepared. The isomeric and sulfur/selenium effects determine the optical, electrochemical, and orbital properties. X-ray crystallography revealed that 2,7-DTF and 3,6-DTF molecules assemble into supramolecular helical structures.