2-溴-4-辛基噻吩 | 189102-85-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 2-溴-4-辛基噻吩
• 英文名称: 2-bromo-3-octylthiophene
• 英文别名: 2-bromo-4-octylthiophene
• CAS: 189102-85-0
• 化学式: C₁₂H₁₉BrS
• 分子量: 275.253
• InChiKey: UCAXOAPMYYUXEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-溴-4-辛基噻吩 、 3,6-二叔丁基咔唑 生成
  参考文献：
  名称：

  Molecular engineering of cyclopentadithiophene-containing organic dyes for dye-sensitized solar cell: Experimental results vs theoretical calculation

  摘要：

  Four donor-conjugated spacer acceptor (D-pi-A) organic dyes containing cyclopentadithiophene unit as a part of the conjugated spacer are prepared and studied to investigate the effects of the conjugated spacer and donor on the short-circuit current and conversion efficiency of the correspondingDSSCs. Theoretical calculations reveal that a shorter conjugated spacer or a stronger donor leads to more effective electron injection upon photo excitation. Therefore, D-pi-A typed dye with longer conjugated spacer may have higher absorption coefficient and longer lambda(max). Nevertheless, it may also have lower effective electron injection upon photo excitation. Calculation data also show that cyclopentadithiophene although is a good moiety for extending the conjugation length of the organic dyes, it also acts as an electron sink, decreasing the effective electron injection. The transition probability calculated with the electron density difference analyses combining with the experimental absorption and photovoltaic performance data provides a useful protocol for designing organic photosensitizers for DSSCs at the electronic and structural levels. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.08.016
• 作为产物：
  描述：

  3-辛基噻吩 在 正丁基锂 、 溴 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.08h， 以92%的产率得到2-溴-4-辛基噻吩
  参考文献：
  名称：

  [EN] A METHOD OF CONTROLLING THE BROMINATION OF THIOPHENE DERIVATIVES
  [FR] PROCÉDÉ PERMETTANT DE MAÎTRISER LA BROMATION DE DÉRIVÉS DE THIOPHÈNE

  摘要：

  提供了一种改进产量的卤代烷基噻吩的区域选择性合成方法。将3-烷基噻吩在-78°C下用n-BuLi激活约1.5小时，然后与溴反应，得到具有良好区域选择性的卤代烷基噻吩。

  公开号：

  WO2011155679A1

文献信息

• A selective and direct synthesis of 2-bromo-4-alkylthiophenes: Convenient and straightforward approaches for the synthesis of head-to-tail (HT) and tail-to-tail (TT) dihexyl-2,2′-bithiophenes
  作者：Ashraf A. El-Shehawy、Nabiha I. Abdo、Ahmed A. El-Barbary、Jae-Suk Lee

  DOI：10.1016/j.tetlet.2010.06.100

  日期：2010.8

  A straightforward method for the synthesis of 2-bromo-4-alkylthiophenes was developed, and the desired products were obtained in the highest chemical yields (>90%) reported to date. 2-Bromo-4-alkylthiophenes were synthesized by regioselective lithiating of 3-alkylthiophenes with n-BuLi and quenching with bromine at 78 degrees C. Moreover, a simple and efficient protocol for the synthesis of dihexyl-2,2'-bithiophenes was developed by employing 2-bromo-4-hexylthiophene instead of the commonly used monomer, 2-bromo-3-hexylthiophene. Kumada and Suzuki cross-coupling reactions were conducted to synthesize the desired products as head-to-tail (HT) and tail-to-tail (TT) regioisomers in high yields and excellent selectivity. (C) 2010 Elsevier Ltd. All rights reserved.