1,4-bis[(4'-N,N-dibutylaminophenyl)ethynyl]-2,5-bis(2',3',4',5',6'-pentafluorophenylethynyl)benzene | 1010439-96-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,4-bis[(4'-N,N-dibutylaminophenyl)ethynyl]-2,5-bis(2',3',4',5',6'-pentafluorophenylethynyl)benzene
• 英文别名: N,N-dibutyl-4-[2-[4-[2-[4-(dibutylamino)phenyl]ethynyl]-2,5-bis[2-(2,3,4,5,6-pentafluorophenyl)ethynyl]phenyl]ethynyl]aniline
• CAS: 1010439-96-9
• 化学式: C₅₄H₄₆F₁₀N₂
• 分子量: 912.957
• InChiKey: GNOYPSJHYLHPAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.3
• 重原子数：
  66
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2,3,4,5,6-五氟碘苯 、 1,4-diethynyl-2,5-bis[(4'-N,N-dibutylaminophenyl)ethynyl]benzene 在 copper(l) iodide 、 四(三苯基膦)钯 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 以100 mg的产率得到1,4-bis[(4'-N,N-dibutylaminophenyl)ethynyl]-2,5-bis(2',3',4',5',6'-pentafluorophenylethynyl)benzene
  参考文献：
  名称：

  Structure−Property Relationships of Fluorinated Donor/Acceptor Tetrakis(phenylethynyl)benzenes and Bis(dehydrobenzoannuleno)benzenes

  摘要：

  Nine new bisdonor/bisacceptor-functionalized tetrakis(phenylethynyl)benzene (TPEB) and six new bis(dehydrobenzoannuleno)benzene (DBA) chromophores have been synthesized. The compounds consist of electron-donating dibutylaniline groups connected through a conjugated phenyl -acetylene scaffold to benzotrifluoride, bis(trifluoromethyl)phenyl, or pentafluorophenyl acceptor groups. In comparison to previously reported analogues utilizing nitrophenyl or benzonitrile acceptor groups, the weaker acceptor groups exhibit visibly fluorescent intramolecular charge transfer (ICT) behavior, moderately narrow optical band gaps, moderately high quantum yields, and strong fluorescence solvatochromism. In this series of molecules, the strongly inductive fluoro acceptor groups result in optical properties similar to the resonance acceptor analogues, making them promising candidates for optical materials device components. The data also support recent investigations that question the utility of using UV/vis spectroscopy alone as a qualitative measure of conjugation. The bisDBAs exhibit weaker ICT behavior and self-association in solution than their corresponding nitro analogues, but show greater stability to decomposition via polymerization and smaller optical band gaps than their acyclic analogues.

  DOI：

  10.1021/jo701740n

文献信息

• Structure−Property Relationships of Fluorinated Donor/Acceptor Tetrakis(phenylethynyl)benzenes and Bis(dehydrobenzoannuleno)benzenes
  作者：Eric L. Spitler、John M. Monson、Michael M. Haley

  DOI：10.1021/jo701740n

  日期：2008.3.1

  Nine new bisdonor/bisacceptor-functionalized tetrakis(phenylethynyl)benzene (TPEB) and six new bis(dehydrobenzoannuleno)benzene (DBA) chromophores have been synthesized. The compounds consist of electron-donating dibutylaniline groups connected through a conjugated phenyl -acetylene scaffold to benzotrifluoride, bis(trifluoromethyl)phenyl, or pentafluorophenyl acceptor groups. In comparison to previously reported analogues utilizing nitrophenyl or benzonitrile acceptor groups, the weaker acceptor groups exhibit visibly fluorescent intramolecular charge transfer (ICT) behavior, moderately narrow optical band gaps, moderately high quantum yields, and strong fluorescence solvatochromism. In this series of molecules, the strongly inductive fluoro acceptor groups result in optical properties similar to the resonance acceptor analogues, making them promising candidates for optical materials device components. The data also support recent investigations that question the utility of using UV/vis spectroscopy alone as a qualitative measure of conjugation. The bisDBAs exhibit weaker ICT behavior and self-association in solution than their corresponding nitro analogues, but show greater stability to decomposition via polymerization and smaller optical band gaps than their acyclic analogues.