5,5'-di(1,2,3-dioxaborolan-2-yl)-2,2'-bithiophene | 925246-82-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5,5'-di(1,2,3-dioxaborolan-2-yl)-2,2'-bithiophene
• 英文别名: 5,5'-di(1,3,2-dioxaborolan-2-yl)-2,2'-bithiophene；5,5'-(C2H4O2B)2-2,2'-dithiophene；2-[5-[5-(1,3,2-Dioxaborolan-2-yl)thiophen-2-yl]thiophen-2-yl]-1,3,2-dioxaborolane；2-[5-[5-(1,3,2-dioxaborolan-2-yl)thiophen-2-yl]thiophen-2-yl]-1,3,2-dioxaborolane
• CAS: 925246-82-8
• 化学式: C₁₂H₁₂B₂O₄S₂
• 分子量: 305.979
• InChiKey: SFNFEHWWNBDZEH-UHFFFAOYSA-N

物化性质

• 沸点：
  541.3±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  93.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,5'-di(1,2,3-dioxaborolan-2-yl)-2,2'-bithiophene 、 3,5-双(4-羧基苯基)碘苯 在 palladium diacetate 、 lithium carbonate 作用下， 以 水 为溶剂， 反应 18.0h， 以73%的产率得到5',5''''-([2,2'-联噻吩]-5,5'-二基)双(([1,1':3',1''-三联苯]-4,4''-二羧酸))
  参考文献：
  名称：

  基于共轭噻吩的轮烷：合成，光谱学和建模。

  摘要：

  甲二噻吩轮烷1个⊂β-CD和其形状持久对应哑铃1合成并充分表征。由分子动力学计算支持的2D NOESY实验揭示了一个非常易移动的大环（β-CD）。溶液中的稳态和时间分辨光致发光实验用于阐明两个系统的激发态动力学，并探索环糊精包封的作用。发现1 ⊂β‐CD的光致发光（PL）光谱相对于哑铃1发生了蓝移（分别为2.81和2.78 eV）。另外，与先前的观察相反，当增加溶液的浓度或改变极性时，PL光谱以及带螺纹和无螺纹系统的衰减动力学均未显示变化，从而提供了缺乏无螺纹主链聚集趋势的证据。

  DOI：

  10.1002/chem.200903353
• 作为产物：
  描述：

  2,2'-联二噻吩 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 16.0h， 生成 5,5'-di(1,2,3-dioxaborolan-2-yl)-2,2'-bithiophene
  参考文献：
  名称：

  Preparation and Properties of Rotaxanes Formed by Dimethyl-β-cyclodextrin and Oligo(thiophene)s with β-Cyclodextrin Stoppers

  摘要：

  [graphics]Novel cyclodextrin rotaxanes with oligothiophene as an axis molecule have been prepared by the Suzuki coupling reaction of 6-O-(4-iodophenyl)-beta-CD (6-I-Ph-beta-CD) with di(1,3,2-dioxaborolan-2-yl)-oligothiophene (oligothiophene diboric ethylene glycol esters) in aqueous solutions of dimethyl-beta-cyclodextrin (DM-beta-CD). These reactions gave [2]rotaxanes and [3]rotaxanes, which were isolated by reversed phase chromatography. The fluorescence intensities of rotaxanes are higher than those of dumbbell-shaped molecules (without DM-beta-CD) in aqueous solutions. The inclusion ratio and chain length of rotaxanes have been found to relate to the emission properties and emission intensities of oligothiophene. In aqueous solutions, fluorescence quantum yields of rotaxanes are higher than those of dumbbell-shaped molecules. The increase in the fluorescence efficiency of rotaxane is caused by suppression of intermolecular interactions, indicating the effect of insulated oligothiophene with DM-beta-CD. beta-CD at the both ends of rotaxanes functions not only as bulky stoppers but also as the recognition site for guest molecules, as verified by fluorescence quenching experiments.

  DOI：

  10.1021/jo061834o

文献信息

• Preparation and Properties of Rotaxanes Formed by Dimethyl-<i>β</i>-cyclodextrin and Oligo(thiophene)s with <i>β</i>-Cyclodextrin Stoppers
  作者：Kazuya Sakamoto、Yoshinori Takashima、Hiroyasu Yamaguchi、Akira Harada

  DOI：10.1021/jo061834o

  日期：2007.1.1

  [graphics]Novel cyclodextrin rotaxanes with oligothiophene as an axis molecule have been prepared by the Suzuki coupling reaction of 6-O-(4-iodophenyl)-beta-CD (6-I-Ph-beta-CD) with di(1,3,2-dioxaborolan-2-yl)-oligothiophene (oligothiophene diboric ethylene glycol esters) in aqueous solutions of dimethyl-beta-cyclodextrin (DM-beta-CD). These reactions gave [2]rotaxanes and [3]rotaxanes, which were isolated by reversed phase chromatography. The fluorescence intensities of rotaxanes are higher than those of dumbbell-shaped molecules (without DM-beta-CD) in aqueous solutions. The inclusion ratio and chain length of rotaxanes have been found to relate to the emission properties and emission intensities of oligothiophene. In aqueous solutions, fluorescence quantum yields of rotaxanes are higher than those of dumbbell-shaped molecules. The increase in the fluorescence efficiency of rotaxane is caused by suppression of intermolecular interactions, indicating the effect of insulated oligothiophene with DM-beta-CD. beta-CD at the both ends of rotaxanes functions not only as bulky stoppers but also as the recognition site for guest molecules, as verified by fluorescence quenching experiments.
• A Conjugated Thiophene-Based Rotaxane: Synthesis, Spectroscopy, and Modeling
  作者：Leszek Zalewski、Michael Wykes、Sergio Brovelli、Massimo Bonini、Thomas Breiner、Marcel Kastler、Florian Dötz、David Beljonne、Harry L. Anderson、Franco Cacialli、Paolo Samorì

  DOI：10.1002/chem.200903353

  日期：2010.4.6

  A dithiophene rotaxane 1⊂β‐CD and its shape‐persistent corresponding dumbbell 1 were synthesized and fully characterized. 2D NOESY experiments, supported by molecular dynamics calculations, revealed a very mobile macrocycle (β‐CD). Steady‐state and time‐resolved photoluminescence experiments in solution were employed to elucidate the excited‐state dynamics for both systems and to explore the effect

  甲二噻吩轮烷1个⊂β-CD和其形状持久对应哑铃1合成并充分表征。由分子动力学计算支持的2D NOESY实验揭示了一个非常易移动的大环（β-CD）。溶液中的稳态和时间分辨光致发光实验用于阐明两个系统的激发态动力学，并探索环糊精包封的作用。发现1 ⊂β‐CD的光致发光（PL）光谱相对于哑铃1发生了蓝移（分别为2.81和2.78 eV）。另外，与先前的观察相反，当增加溶液的浓度或改变极性时，PL光谱以及带螺纹和无螺纹系统的衰减动力学均未显示变化，从而提供了缺乏无螺纹主链聚集趋势的证据。