5-溴-3,3'-二己基-2,2'-联噻吩 | 154717-20-1

• 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
• 中文名称: 5-溴-3,3'-二己基-2,2'-联噻吩
• 英文名称: 5-bromo-3,3'-dihexyl-2,2'-bithiophene
• 英文别名: 5-Bromo-3-hexyl-2-(3-hexylthiophen-2-yl)thiophene
• CAS: 154717-20-1
• 化学式: C₂₀H₂₉BrS₂
• 分子量: 413.486
• InChiKey: IKAMVPZNOKLJTG-UHFFFAOYSA-N

物化性质

• 沸点：
  467.3±45.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-溴-3,3'-二己基-2,2'-联噻吩 在 N-溴代丁二酰亚胺(NBS) 、 铜 作用下， 生成 5-bromo-3,3'-dihexyl-5'-methoxy-2,2'-bithiophene
  参考文献：
  名称：

  溶剂对头-头和头-尾方向推挽二己基联噻吩的红移的影响

  摘要：

  合成了具有HH和HT方向的推挽二己基联噻吩。从它们的电子吸收光谱的溶剂效应表明，尽管它们之间共轭的分子平面性差异很大，但由于这些取向异构体之间由于溶剂极性引起的稳定能几乎相同。

  DOI：

  10.1016/0040-4039(96)00070-6
• 作为产物：
  描述：

  3,3'-二溴-2,2'-联噻吩 在 N-溴代丁二酰亚胺(NBS) 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 作用下， 以 四氢呋喃 为溶剂， 生成 5-溴-3,3'-二己基-2,2'-联噻吩
  参考文献：
  名称：

  Palladium-Catalyzed C−H Homocoupling of Bromothiophene Derivatives and Synthetic Application to Well-Defined Oligothiophenes

  摘要：

  Synthesis of oligothiophenes of well-defined structures that possess 2-8 thiophene units is performed with a new synthetic strategy involving C-H homocoupling of bromothiophenes and cross-coupling with organostannanes. Tolerance of the carbon-bromine bond to the palladium-catalyzed C-H homocoupling results in oligothiophenes bearing C-Br bonds at the terminal thiophene rings, which allow further transformation by the catalysis of a transition-metal complex.

  DOI：

  10.1021/ja060749v

文献信息

• Syntheses and Properties of Unsymmetrically Substituted Bi- and Quaterthiophenes
  作者：Hiroyuki Higuchi、Yoshiyuki Uraki、Hiroki Yokota、Haruki Koyama、Juro Ojima、Tatsuo Wada、Hiroyuki Sasabe

  DOI：10.1246/bcsj.71.483

  日期：1998.2

  The unsymmetrically substituted bi- and quaterthiophene derivatives were synthesized. The unsymmetrically substituted bithiophenes carrying the electron-withdrawing substituent X on one of the outer thiophene rings exhibited the maxima of absorption bands at the longer wavelengths than the symmetrically disubstituted bithiophene derivatives, while the unsymmetrical quaterthiophenes had such maxima

  合成了不对称取代的双和四噻吩衍生物。在外噻吩环之一上带有吸电子取代基 X 的不对称取代的联噻吩在比对称双取代的联噻吩衍生物更长的波长处表现出吸收带的最大值，而不对称的四联噻吩在比相应的对称性更短的波长处具有这样的最大值那些。在带有推拉取代基的双或四噻吩的情况下，由于吸电子取代基 X 导致的最长波长吸收带的红移趋势更为明显。不对称四噻吩表现出比相应的联噻吩更大的三阶非线性光学（TNLO）特性，类似于对称双噻吩和四噻吩之间的情况。然而，不对称双噻吩和四噻吩的 TNLO 特性显示不依赖于吸电子强度......
• Simple Separation of an Isomeric Mixture of Dihexylbithiophenes with Head-to-head and Head-to-tail Orientations
  作者：Hiroyuki Higuchi、Noriyuki Hayashi、Haruki Koyama、Juro Ojima

  DOI：10.1246/cl.1995.1115

  日期：1995.12

  The isomeric mixture of 3,3′-dialkylbithiophenes with head-to-head (H-H) and head-to-tail (H-T) orientations was separated into each isomer by using preferential brominartion of the H-T isomer. This separation method proved to be useful for simultaneous preparation of the pure H-H and H-T bithiophenes which are inaccessable by other methods.

  3,3′-二烷基二噻吩的异构体混合物采用优先溴化H-T异构体的方法分离成各个异构体。这种分离方法被证明对于同时制备纯的H-H和H-T二噻吩非常有效，而其他方法无法获得这两种异构体。
• Synthesis and Properties of<i>α</i>,<i>ω</i>-Disubstituted Oligo(3-hexylthiophene)s and Oligothienoquinonoids in Head-to-head Orientation
  作者：Hiroyuki Higuchi、Taketoshi Nakayama、Haruki Koyama、Juro Ojima、Tatsuo Wada、Hiroyuki Sasabe

  DOI：10.1246/bcsj.68.2363

  日期：1995.8

  The two types of highly-ordered oligo(3-hexylthiophene)s in head-to-head orientation, a series of α,ω-disubstituted oligothiophenes and a series of bis(dicyanomethylene)oligothienoquinonoids, were synthesized. The properties of these compounds are discussed on the basis of the electronic spectra and cyclic voltammetry.

  合成了两种头对头取向的高度有序的寡聚（3-己基噻吩），一系列α,ω-二取代的寡噻吩和一系列双（氰亚甲基）寡噻吩醌类化合物。基于电子光谱和循环伏安法，讨论了这些化合物的性质。
• Precise Control of Quantum Dot Location within the P3HT-<i>b</i>-P2VP/QD Nanowires Formed by Crystallization-Driven 1D Growth of Hybrid Dimeric Seeds
  作者：Yong-Jae Kim、Chul-Hee Cho、Kwanyeol Paek、Mijung Jo、Mi-kyoung Park、Na-Eun Lee、Youn-joong Kim、Bumjoon J. Kim、Eunji Lee

  DOI：10.1021/ja410165f

  日期：2014.2.19

  bridged by P3HT-b-P2VP polymers were generated during the initial state of crystallization. These, in turn, assemble into elongated fibrils, forming the coaxial P3HT-b-P2VP/QDs hybrid NWs. In particular, the location of the QD arrays within the single strand of P3HT-b-P2VP can be controlled precisely by manipulating the regioregularity (RR) values of P3HT block and the relative lengths of P2VP block. The

  在此，我们报告了通过利用聚（3-己基噻吩）的结晶驱动溶液组装简单制造由 p 型共轭聚合物（CP）和 n 型无机量子点（QD）组成的混合纳米线（NW）- b-聚（2-乙烯基吡啶）（P3HT-b-P2VP）棒状线圈两亲物。通过系统的透射电子显微镜实验可视化混合 NW 的结晶驱动生长演变表明，在初始结晶状态期间生成了由 P3HT-b-P2VP 聚合物桥接的离散二聚体 CdSe QD。这些反过来组装成细长的原纤维，形成同轴的 P3HT-b-P2VP/QDs 混合 NW。特别是，P3HT-b-P2VP 单链中 QD 阵列的位置可以通过操纵 P3HT 块的区域规则 (RR) 值和 P2VP 块的相对长度来精确控制。QD 阵列的同轴度取决于 P3HT 块的噻吩环的共面性，这可以通过 P3HT 块的 RR 值控制。此外，根据量子点的表面特征，可以在 P3HT-b-P2VP NW 的特定局部位点调节量子点的
• Orientation and Substituent Effects on the Properties of the Diacetylene-Group Connected Octaethylporphyrin–Dihexylbithiophene Derivatives (OEP–DHBTh–X) Carrying Electron-Withdrawing Groups
  作者：Naoto Hayashi、Takashi Nishihara、Takuya Matsukihira、Hiroki Nakashima、Keiko Miyabayashi、Mikio Miyake、Hiroyuki Higuchi

  DOI：10.1246/bcsj.80.371

  日期：2007.1.15

  Orientational isomers of the octaethylporphyrin–dihexylbithiophene (OEP–DHBTh) derivatives connected with a diacetylene linkage were synthesized, with various electron-withdrawing substituents X attached at the ends. The effects of DHBTh orientation and X substituent on the properties of OEP–DHBTh–X (X = H, Br, CN, CHO, and NO2) were studied and compared with those of related OEP derivatives.

  合成了连接有二炔基链的八乙基卟啉-二己基二噻苯（OEP-DHBTh）异构体，末端附有不同的电子吸引取代基X。研究了DHBTh方向和X取代基对OEP-DHBTh-X（X = H, Br, CN, CHO和NO2）性质的影响，并与相关OEP衍生物进行了比较。