8-(3,5-dibromophenyl)-4,4'-difluoro-3a,4a-diaza-s-indacene | 1126901-44-7

• 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: 8-(3,5-dibromophenyl)-4,4'-difluoro-3a,4a-diaza-s-indacene
• 英文别名: 8-(3,5-dibromophenyl)-BODIPY；10-(3,5-Dibromophenyl)-5,5-difluoro-5H-dipyrrolo[1,2-c:2 inverted exclamation mark,1 inverted exclamation mark-f][1,3,2]diazaborinin-4-ium-5-uide；8-(3,5-dibromophenyl)-2,2-difluoro-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• CAS: 1126901-44-7
• 化学式: C₁₅H₉BBr₂F₂N₂
• 分子量: 425.866
• InChiKey: PVCGJLZMICXFPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  7.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-(3,5-dibromophenyl)-4,4'-difluoro-3a,4a-diaza-s-indacene 、 4-二甲基氨基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 以69%的产率得到4-[3-(2,2-difluoro-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)-5-[4-(dimethylamino)phenyl]phenyl]-N,N-dimethylaniline
  参考文献：
  名称：

  Novel meso-Polyarylamine-BODIPY Hybrids: Synthesis and Study of Their Optical Properties

  摘要：

  A series of 14 meso-polyarylamine-BODIPY (borondipyrromethene) hybrids of the general structure A were synthesized. Two methods were used to prepare them. The first protocol involved a direct Liebeskind-Srogl cross-coupling of thiomethylbodipys 1-2 with arylaminoboronic acids (4 examples, 75-98%). The second method involves a two-step sequence: a Liebeskind-Srogl reaction to prepare 6 meso-bromoarylbodipys (58-83%) followed by a Suzuki coupling of these Br-containing BODIPYs with arylaminoboronic acids (10 examples, 44-84%). Seven of these derivatives displayed emission in the near-infrared region. The optical properties of compound 18 were rationalized in terms of its crystal structure.

  DOI：

  10.1021/jo802519b
• 作为产物：
  描述：

  [2-[(甲硫基)(2H-吡咯-2-亚基)甲基]-1H-吡咯](二氟硼烷) 、 3,5-二溴苯硼酸 在 噻吩-2-甲酸亚铜(I) 、 tris(dibenzylideneacetone)dipalladium (0) 、 三(2-呋喃基)膦 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到8-(3,5-dibromophenyl)-4,4'-difluoro-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Novel meso-Polyarylamine-BODIPY Hybrids: Synthesis and Study of Their Optical Properties

  摘要：

  A series of 14 meso-polyarylamine-BODIPY (borondipyrromethene) hybrids of the general structure A were synthesized. Two methods were used to prepare them. The first protocol involved a direct Liebeskind-Srogl cross-coupling of thiomethylbodipys 1-2 with arylaminoboronic acids (4 examples, 75-98%). The second method involves a two-step sequence: a Liebeskind-Srogl reaction to prepare 6 meso-bromoarylbodipys (58-83%) followed by a Suzuki coupling of these Br-containing BODIPYs with arylaminoboronic acids (10 examples, 44-84%). Seven of these derivatives displayed emission in the near-infrared region. The optical properties of compound 18 were rationalized in terms of its crystal structure.

  DOI：

  10.1021/jo802519b

文献信息

• Addressing fluorescence and liquid crystal behaviour in multi-mesogenic BODIPY materials
  作者：Michael Benstead、Geraldine A. Rosser、Andrew Beeby、Georg H. Mehl、Ross W. Boyle

  DOI：10.1039/c0nj00990c

  日期：——

  Two series of BODIPYs (4,4′-difluoro-3a,4a-diaza-s-indacene) bearing mesogenic substituents have been synthesised and their fluorescent and self-assembly behaviour has been observed and characterised. In order to induce a strong preference for liquid crystallinity, two mesogenic units have been attached to each fluorophore. The compounds were prepared by microwave-assisted Suzuki couplings in moderate yields. Two different, but related, mesogens were employed but only one series was found to exhibit the formation of liquid crystal mesophases. Monotropic nematic phases, observed by differential scanning calorimetry (DSC) and optical polarising microscopy (OPM), were adopted over varying temperature ranges depending on the degree of alkyl substitution on the fluorophore. Increasing alkyl substitution caused a gradual increase in fluorescence quantum yield due to rotational restriction of the BODIPY 8-phenyl ring, however, this also disrupted the formation of the nematic phase causing a reduction in the temperature range over which the mesophase was exhibited. The large, branched structure of the compounds prepared caused them to have a high viscosity in both the nematic and isotropic liquid phase. Due to the high viscosity, the Schlieren texture of the nematic phase could only be observed after several hours annealing.

  合成了两系列具有介电取代基的BODIPYs（4,4′-二氟-3a,4a-二氮杂-苊烯），并观察和表征了它们的荧光和自组装行为。为了增强液晶性的强烈偏好，在每个荧光团上附加了两个介电单元。该化合物通过微波辅助的铃木偶联反应以适中的产率制备。使用了两种不同但相关的介电物质，但仅发现一系列化合物表现出液晶中间相的形成。通过差示扫描量热法（DSC）和光学偏振显微镜（OPM）观察到的单晶向列相，根据荧光团上烷基取代的程度，在不同温度范围内呈现。随着烷基取代的增加，由于对BODIPY 8-苯基环的旋转限制，荧光量子产率逐渐提高，但这也干扰了向列相的形成，导致液晶中间相表现的温度范围减少。所制备化合物的大型支化结构导致它们在向列相和各向同性液相中均具有高粘度。由于粘度较高，向列相的条纹纹理仅在经过数小时的退火后才能观察到。
• Novel <i>meso</i>-Polyarylamine-BODIPY Hybrids: Synthesis and Study of Their Optical Properties
  作者：Erik Lager、Jianzhao Liu、Angélica Aguilar-Aguilar、Ben Zhong Tang、Eduardo Peña-Cabrera

  DOI：10.1021/jo802519b

  日期：2009.3.6

  A series of 14 meso-polyarylamine-BODIPY (borondipyrromethene) hybrids of the general structure A were synthesized. Two methods were used to prepare them. The first protocol involved a direct Liebeskind-Srogl cross-coupling of thiomethylbodipys 1-2 with arylaminoboronic acids (4 examples, 75-98%). The second method involves a two-step sequence: a Liebeskind-Srogl reaction to prepare 6 meso-bromoarylbodipys (58-83%) followed by a Suzuki coupling of these Br-containing BODIPYs with arylaminoboronic acids (10 examples, 44-84%). Seven of these derivatives displayed emission in the near-infrared region. The optical properties of compound 18 were rationalized in terms of its crystal structure.