2,2'''-Dibromo-4,4',4'',4''',5,5',5'',5'''-octamethoxy-1,1':2',1'':2'',1'''-quaterphenyl | 1265899-73-7

• 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: 2,2'''-Dibromo-4,4',4'',4''',5,5',5'',5'''-octamethoxy-1,1':2',1'':2'',1'''-quaterphenyl
• 英文别名: 1-bromo-2-[2-[2-(2-bromo-4,5-dimethoxyphenyl)-4,5-dimethoxyphenyl]-4,5-dimethoxyphenyl]-4,5-dimethoxybenzene
• CAS: 1265899-73-7
• 化学式: C₃₂H₃₂Br₂O₈
• 分子量: 704.409
• InChiKey: KQCNLZNWCHZYTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2'''-Dibromo-4,4',4'',4''',5,5',5'',5'''-octamethoxy-1,1':2',1'':2'',1'''-quaterphenyl 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 N-溴代丁二酰亚胺(NBS) 、 叔丁基锂 、 palladium diacetate 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 26.67h， 生成 Benzyl 2-[2-[2-[2-[2-(4,5-dimethoxy-2-phenylmethoxycarbonylphenyl)-4,5-dimethoxyphenyl]-4,5-dimethoxyphenyl]-4,5-dimethoxyphenyl]-4,5-dimethoxyphenyl]-4,5-dimethoxybenzoate
  参考文献：
  名称：

  Remarkable Effects of Terminal Groups and Solvents on Helical Folding of o-Phenylene Oligomers

  摘要：

  Although o-phenylene oligomers (OPnR) made of dimethoxyphenylene units are thought to be intrinsically dynamic due to pi-electronic repulsion, we show that they fold into a regular helical geometry in CH3CN when they carry terminal groups such as CH3, CH2OH, Br, CO2Bn, and NO2. We evaluated their helical inversion kinetics via optical resolution of long-chain oligomers (e.g. 16- and 24-mers) by chiral HPLC. OP24Br at 298 K shows a half-life for the optical activity of 5.5 h in CH3OH/water (7/3 v/v) and requires 34 h for complete racemization. The perfectly folded helical conformers of OPnR, unlike their imperfectly folded ones, are devoid of extended pi-conjugation and show a cyclic voltammogram featuring reversible multistep oxidation waves.

  DOI：

  10.1021/ja303117z

文献信息

• <i>o</i>-Phenylene Octamers as Surface Modifiers for Homeotropic Columnar Ordering of Discotic Liquid Crystals
  作者：Takashi Kajitani、Yuki Suna、Atsuko Kosaka、Terutsune Osawa、Shigenori Fujikawa、Masaki Takata、Takanori Fukushima、Takuzo Aida

  DOI：10.1021/ja4087853

  日期：2013.10.2

  Large area homeotropic columnar ordering of pi-conjugated discotic liquid crystals (LCs) is crucial for certain device applications but generally hard to achieve. Here we report polymeric p-phenylene octamer poly-1 and its monomer 1 as the first surface modifiers for homeotropic columnar order of a variety of discotic LCs up to a macroscopic length scale. Their octameric o-phenylene parts are known to fold helically into a cylinder that is reminiscent of a pi-stacked column of discotic LCs. Through-view X-ray diffraction patterns of 1 suggested that this molecule adheres to the glass substrate and directs its cylindrical axis perpendicular to the glass surface. This face on orientation likely nucleates the homeotropic columnar order of discotic LC materials.
• Remarkable Effects of Terminal Groups and Solvents on Helical Folding of <i>o</i>-Phenylene Oligomers
  作者：Shinji Ando、Eisuke Ohta、Atsuko Kosaka、Daisuke Hashizume、Hiroyuki Koshino、Takanori Fukushima、Takuzo Aida

  DOI：10.1021/ja303117z

  日期：2012.7.11

  Although o-phenylene oligomers (OPnR) made of dimethoxyphenylene units are thought to be intrinsically dynamic due to pi-electronic repulsion, we show that they fold into a regular helical geometry in CH3CN when they carry terminal groups such as CH3, CH2OH, Br, CO2Bn, and NO2. We evaluated their helical inversion kinetics via optical resolution of long-chain oligomers (e.g. 16- and 24-mers) by chiral HPLC. OP24Br at 298 K shows a half-life for the optical activity of 5.5 h in CH3OH/water (7/3 v/v) and requires 34 h for complete racemization. The perfectly folded helical conformers of OPnR, unlike their imperfectly folded ones, are devoid of extended pi-conjugation and show a cyclic voltammogram featuring reversible multistep oxidation waves.