bis{3,4-dibutyl-2-thienylethynyl-5-(3,4-dibutyl-5-iodo-2-thienylethynyl)}ethyne | 922166-74-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: bis{3,4-dibutyl-2-thienylethynyl-5-(3,4-dibutyl-5-iodo-2-thienylethynyl)}ethyne
• 英文别名: bis[3,4-dibutyl-5-(3,4-dibutyl-5-iodo-2-thienylethynyl)-2-thienyl]acetylene
• CAS: 922166-74-3
• 化学式: C₅₄H₇₂I₂S₄
• 分子量: 1103.24
• InChiKey: XJPOCVUGDLLWPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.08
• 重原子数：
  60.0
• 可旋转键数：
  24.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  bis{3,4-dibutyl-2-thienylethynyl-5-(3,4-dibutyl-5-iodo-2-thienylethynyl)}ethyne 、 3,4-dibutyl-2-(3,4-dibutylthien-2-ylethynyl)-5-ethynylthiophene 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 反应 2.0h， 以88%的产率得到
  参考文献：
  名称：

  Synthesis, Structures, and Photophysical Properties of π-Expanded Oligothiophene 8-mers and Their Saturn-Like C₆₀ Complexes

  摘要：

  Two isomers of a multifunctional pi-expanded macrocyclic oligothiophene 8-mer, E,E-1 and Z,Z-1, were synthesized using a McMurry coupling of a dialdehyde composed of four 2,5-thienylene and three ethynylene units under high dilution conditions. On the other hand, cydo [8]-(2,5-thienylene-ethynylene) 2 was synthesized by intramolecular Sonogashira cydization of ethynyl bromide 5. From STM measurements, both E,E-1 and Z,Z-1 formed self-assembled monolayers at the solid liquid interface to produce porous networks, and from X-ray analyses of E,E-1 and 2, both compounds had a round shape with a honeycomb stacked structure. E,E-1 formed various fibrous polymorphs due to nanophase separation of the macrorings. E,E-1 and Z,Z-1 in solution exhibited photochromism upon irradiation and UV light, respectively, and this photoisomerization was confirmed by using STM. Furthermore, amorphous films of Z,Z-1 and E,E-1 showed photoisomerization, although single crystals, fibers, and square tubes of E,E-1 remained unchanged under similar conditions. E,E-1 with a 12.5-14.7 angstrom inner cavity incorporated fullerene C-60 in the cavity in solution and the solid state to produce a Saturn-like complex, whose structure was determined by X-ray analysis. 2 also formed a Saturn-like complex with C-60 in the solid state. These Saturn-like complexes are stabilized by van der Waals interactions between the sulfur atoms of 8-mer and C-60. The complexes exhibited charge-transfer interactions in the solid state. Like E,E-1, Saturn-like complex E,E-1 superset of C-60 formed small cube and fiber structures depending on the solvent used, whereas those of Saturn-like complex 2 superset of C-60 were limited due to the rigidity of the macroring of 2.

  DOI：

  10.1021/jacs.5b00291
• 作为产物：
  描述：

  bis{3,4-dibutyl-2-thienylethynyl-5-(3,4-dibutyl-2-thienylethynyl)}ethyne 在 正丁基锂 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以86%的产率得到bis{3,4-dibutyl-2-thienylethynyl-5-(3,4-dibutyl-5-iodo-2-thienylethynyl)}ethyne
  参考文献：
  名称：

  由噻吩、乙炔和乙烯结构单元组成的巨型大环化合物

  摘要：

  设计了具有 60pi、90pi、120pi、150pi 和 180pi 框架（1、2、3、4 和 5）的完全共轭巨环低聚噻吩及其丁基取代衍生物（1a、2a、3a、4a 和 5a）已经使用改良的 Sonogashira 和 McMurry 偶联反应作为关键步骤合成。60-180pi 系统 1-5 是具有 1.8-6 nm 内腔和 3.3-7.5 nm 外分子直径的圆形。已使用溴化/脱溴化氢程序将含有 10 个 3,4-二丁基-2,5-噻吩基、8 个亚乙炔基和两个亚乙烯基单元的化合物 1a 转化为大环低聚（3,4-二丁基-2,5-噻吩基-乙炔基）6a . 与具有五个噻吩环的线性共轭对应物相比，巨型大环 1a-6a 表现出其吸收光谱的红移和具有较大斯托克斯位移的相当强的荧光。化合物 1a-6a 表现出多步可逆氧化还原行为，具有相当低的第一氧化电位，反映了它们的循环共轭。此外，由于分子内和分子间 pi-pi

  DOI：

  10.1021/ja067077t

文献信息

• π-Expanded Cyclic Oligothiophene 12-Mers as Semishape-Persistent Macrocycles
  作者：Masahiko Iyoda、Mika Imamura、Hideyuki Shimizu、Jun Yamakawa、Hiroyuki Otani、Tohru Nishinaga

  DOI：10.3987/com-16-s(s)29

  日期：——

  pi-Expanded macrocyclic oligothiophene 12-mer E,E-12T10A, 18-mer E,E,E-18T15A, and 24-mer E,E,E,E-24T20A composed of thienylene, ethynylene, and vinylene moieties were synthesized in good total yield by the McMurry coupling reaction of dialdehyde 1. E,E-12T10A was converted to cyclo[12](3,4-dibutyl-2,5-thienylene-ethynylene) 12T12A in 20% yield by bromination-dehydrobromination procedure. Furthermore, the synthesis of 12T12A was carried out by using double elimination procedure starting from the sulfone dianion 2(2-) and dialdehyde 1. The crystal structure of E,E-12T10A was determined by X-ray analysis. In the solid state, macrocyclic oligothiophenes formed nanostructured polymorphs such as single crystals, petal-shaped structure, and chained lumps depending on the ring size.