3,4-二丁基-2-乙炔基噻吩 | 565186-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 3,4-二丁基-2-乙炔基噻吩
• 英文名称: 3,4-dibutyl-2-ethynylthiophene
• 英文别名: Thiophene, 3,4-dibutyl-2-ethynyl-
• CAS: 565186-13-2
• 化学式: C₁₄H₂₀S
• 分子量: 220.379
• InChiKey: UTGWFDLRIGOITG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  3,4-二丁基-2-乙炔基噻吩 在 sodium sulfide 、 四甲基乙二胺 、 氧气 、 copper(l) chloride 作用下， 以 二氯甲烷 、 乙二醇甲醚 为溶剂， 反应 27.0h， 生成 3,3'',4,4''-Tetrabutyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Homologous series of regioregular alkylsubstituted oligothiophenes up to an 11-mer

  摘要：

  A complete series of structurally well-defined butylated oligothiophenes up to an Il-mer was synthesized by a combination of aryl-aryl cross-coupling reactions and cyclization of 1,3-butadiyne precursors with sulfide anions. Palladium-catalyzed cross-coupling of halogenated thiophene units with trimethylsilylacetylene effectively yields ethynylated thiophenes which after deprotection are oxidatively coupled to the corresponding 1,3-butadiynes. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)00254-x
• 作为产物：
  描述：

  3,4-二丁基噻吩 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 碘 、 potassium carbonate 、 二异丙胺 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 7.5h， 生成 3,4-二丁基-2-乙炔基噻吩
  参考文献：
  名称：

  2，5-二乙炔基-3,4-二丁基噻吩桥连的背对背三联吡啶配体的简明模块化合成。

  摘要：

  带有数量不断增加的2,5-二乙炔基-3,4-二丁基噻吩（DEDBT）组件的可溶性和刚性基于联吡啶的对位配体的有效合成证明了在最后一步中基于双偶联的单一收敛策略的优势带有足够数量的噻吩模块的二吡啶并带有二碘取代的噻吩亚基的单体。该方案既具有效率又具有多功能性的优点，并且需要关键的中间体，这些中间体是通过逐步实现单萜吡啶片段而制备的，其中的关键噻吩中间体带有碘官能团，炔丙基保护基和两个丁基增溶剂碎片。生产所有中间体和最终配体需要一组实验条件。在铜盐和氧的存在下，带有一个或两个噻吩取代基的单取代三联吡啶骨架的氧化二聚作用，在铜盐和氧的存在下，提供了带有中心二噻吩基丁二炔间隔基的同位配体。已经研究了新型低聚物的光学性质，并根据有效的共轭长度和π电子共轭进行了讨论。随着散布的DEDBT单元数量的增加，观察到吸收和荧光跃迁的能量以及量子产率的显着降低。已经研究了新型低聚物的光学性质，并根据有效的共轭长

  DOI：

  10.1021/jo020679k

文献信息

• Linear and nonlinear optical properties of a quadrupolar carbo-benzene and its benzenic parent: The carbo-merization effect
  作者：Rodrigo M. Barba-Barba、Marwa Chammam、Gabriel Ramos-Ortiz、Dymytrii Listunov、Jayaramakrishnan Velusamy、Mario Rodriguez、Ramon Carriles、Carlos Silva、Carine Duhayon、Brice Kauffmann、Valérie Maraval、Remi Chauvin

  DOI：10.1016/j.dyepig.2021.109133

  日期：2021.4

  their benzene parent in the wavelength range 650–950 nm, with a maximum of σ2PA = 1430 GM (1 GM = 10−50 cm4 s/photon). Beyond a moderate nonlinearity, this comparative study provides quantitative insights about the way carbo-merization or insertion of a π-conjugated macrocycle between chromophoric functions (here thiophene rings) can tune optical properties of organic molecules. The optical properties

  在此，对噻吩官能化的四极碳苯和一般结构为Th–C C– [core] –C C–Th，Th = R 2 C 4 HS的苯型母体的光学性质进行了比较研究。除了以前未知的二辛基噻吩基乙炔基苯（核心=  p -C 6 H 4，R =  n Oct）之外，还考虑了两个双-二烷基噻吩基乙炔基-碳-苯（core = C 18 Ph 4，R =  n Oct，n Bu）C 18的“碳-芳香族”特征大循环。从相应的乙炔基噻吩分别以47％，20％和10％的收率合成这三个靶标，然后通过经典方法（如NMR光谱学和X射线晶体学）对一种碳苯进行表征。关于线性和非线性光学性质，我们的结果表明，碳母化诱导单光子电子激发的低能显着转移，同时摩尔消光系数比母体分子增加8倍。有趣的是，这些激励导致光致发光包括所述类型的衰减转变的宽频带š 1 →小号0但类型的也S 2 → S 0。与Kasha法则相反，这种来自较高激发态的发射现象被归因于-或通过-S
• Giant Macrocycles Composed of Thiophene, Acetylene, and Ethylene Building Blocks
  作者：Kazumi Nakao、Masayuki Nishimura、Tomoya Tamachi、Yoshiyuki Kuwatani、Hitoshi Miyasaka、Tohru Nishinaga、Masahiko Iyoda

  DOI：10.1021/ja067077t

  日期：2006.12.1

  units has been converted into macrocyclic oligo(3,4-dibutyl-2,5-thienylene-ethynylene) 6a using bromination/dehydrobromination procedure. Giant macrocycles 1a-6a exhibit a red shift of their absorption spectra and a fairly strong fluorescence with a large Stokes shift as compared to a linear conjugated counterpart having five thiophene rings. Compounds 1a-6a exhibit multistep reversible redox behaviors

  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
• Synthesis, Structures, and Photophysical Properties of π-Expanded Oligothiophene 8-mers and Their Saturn-Like C₆₀ Complexes
  作者：Hideyuki Shimizu、José D. Cojal González、Masashi Hasegawa、Tohru Nishinaga、Tahmina Haque、Masayoshi Takase、Hiroyuki Otani、Jürgen P. Rabe、Masahiko Iyoda

  DOI：10.1021/jacs.5b00291

  日期：2015.3.25

  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.
• Homologous series of regioregular alkylsubstituted oligothiophenes up to an 11-mer
  作者：Jens Krömer、Peter Bäuerle

  DOI：10.1016/s0040-4020(01)00254-x

  日期：2001.4

  A complete series of structurally well-defined butylated oligothiophenes up to an Il-mer was synthesized by a combination of aryl-aryl cross-coupling reactions and cyclization of 1,3-butadiyne precursors with sulfide anions. Palladium-catalyzed cross-coupling of halogenated thiophene units with trimethylsilylacetylene effectively yields ethynylated thiophenes which after deprotection are oxidatively coupled to the corresponding 1,3-butadiynes. (C) 2001 Published by Elsevier Science Ltd.
• A Concise Modular Synthesis of 2,5-Diethynyl-3,4-dibutyl-thiophene-Bridged Back-to-Back Terpyridine Ligands
  作者：Celine Ringenbach、Antoinette De Nicola、Raymond Ziessel

  DOI：10.1021/jo020679k

  日期：2003.6.1

  The efficient synthesis of soluble and rigid terpyridine-based ditopic ligands bearing an increasing number of 2,5-diethynyl-3,4-dibutylthiophene (DEDBT) modules has demonstrated the advantages of a single convergent strategy based on a double coupling in a final step of monoterpyridine building blocks carrying the adequate number of thiophene modules with a diiodo-substituted thiophene subunit. This

  带有数量不断增加的2,5-二乙炔基-3,4-二丁基噻吩（DEDBT）组件的可溶性和刚性基于联吡啶的对位配体的有效合成证明了在最后一步中基于双偶联的单一收敛策略的优势带有足够数量的噻吩模块的二吡啶并带有二碘取代的噻吩亚基的单体。该方案既具有效率又具有多功能性的优点，并且需要关键的中间体，这些中间体是通过逐步实现单萜吡啶片段而制备的，其中的关键噻吩中间体带有碘官能团，炔丙基保护基和两个丁基增溶剂碎片。生产所有中间体和最终配体需要一组实验条件。在铜盐和氧的存在下，带有一个或两个噻吩取代基的单取代三联吡啶骨架的氧化二聚作用，在铜盐和氧的存在下，提供了带有中心二噻吩基丁二炔间隔基的同位配体。已经研究了新型低聚物的光学性质，并根据有效的共轭长度和π电子共轭进行了讨论。随着散布的DEDBT单元数量的增加，观察到吸收和荧光跃迁的能量以及量子产率的显着降低。已经研究了新型低聚物的光学性质，并根据有效的共轭长

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