5,5"-dimethyl-[2,2':3',2"]terthiophene | 1231767-25-1

• 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
• 英文名称: 5,5"-dimethyl-[2,2':3',2"]terthiophene
• 英文别名: 5,5''-dimethyl-2,2':3',2''-terthiophene；2,3-bis(5-methylthiophen-2-yl)thiophene
• CAS: 1231767-25-1
• 化学式: C₁₄H₁₂S₃
• 分子量: 276.447
• InChiKey: KEZMAEFZYGLNKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,5"-dimethyl-[2,2':3',2"]terthiophene 在 正丁基锂 、 水 、 N,N'-二环己基碳二亚胺 、 DPTS 、 potassium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 157.0h， 生成 2-(2-Methylprop-2-enoyloxy)ethyl 5-[5-[4-[4,5-bis(5-methylthiophen-2-yl)thiophen-2-yl]-5-[5-(5-methylthiophen-2-yl)-4-(5-methylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophene-2-carboxylate
  参考文献：
  名称：

  通过噻吩树突空间重叠的棒状大分子。

  摘要：

  通过逐步交叉偶联反应并在焦点处引入乙烯基，合成了两种用电活性共轭噻吩低聚物官能化的新型树枝状大分子单体7和8。通过使用自由基聚合法将两种大分子单体聚合成树枝状聚合物9和10。树枝状聚合物9和10的光物理和氧化还原行为与相应的大分子单体明显不同。当树枝状分子连接到聚合物骨架上时，这种差异可能是由于噻吩树枝状分子通过π-π相互作用而在空间上重叠造成的。树枝状聚合物可以组织成厚度为4.8 nm的大面积二维薄片。具有全部树突状噻吩侧链的聚合物9通过部分掺杂碘或四氟硼酸硝基硼（NOBF 4）表现出增强的电导率。新型两亲树状聚合物15是通过大分子单体7的原子转移自由基聚合反应从聚乙二醇（PEG）大分子引发剂合成而来的，发现它在水中具有自组织结构。

  DOI：

  10.1002/chem.201003627
• 作为产物：
  描述：

  2-甲基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 magnesium 作用下， 以 乙醚 为溶剂， 生成 5,5"-dimethyl-[2,2':3',2"]terthiophene
  参考文献：
  名称：

  Emission behavior of a symmetrical sexthiophene

  摘要：

  Detailed absorption and emission behavior were investigated for a sexthiophene molecule in solution, film, and solid. Only strong polarity solvent could result a notable influence on the quench of its fluorescence. In weak and medium polar environment, including in polymer matrix, highly emissive behavior was maintained and exhibit large Stokes shift. More important is its highly emissive in solid state due to the twisted molecular conformation. However, the bandwidth of solid emission (FWHM: 2149 cm(-1)) is similar to that of solution emission. The calculated frontier orbital based on TDDFT theory uncovered the underlying signal mechanism furtherly.

  DOI：

  10.1080/15421406.2016.1277497

文献信息

• Studies on the preference of multiple coupling in the introduction of thiophene ring into poly-halogenated aromatic compounds with nickel NHC catalyst
  作者：Shota Tanaka、Go Tatsuta、Atsushi Sugie、Atsunori Mori

  DOI：10.1016/j.tetlet.2013.01.127

  日期：2013.4

  Several thiophene derivatives can be deprotonated by the combination of ethyl magnesium chloride (EtMgCl) and a catalytic amount of 2,2,6,6-tetramethylpiperidine (TMP-H). The metalated 3-hexylthiophene reacts with 2,3- and 2,5-dibromothiophenes in the presence of a nickel catalyst bearing NHC ligand (IPr) to afford the di-coupled product exclusively along with recovery of dibromothiophene albeit the

  几种噻吩衍生物可以通过乙基氯化镁（EtMgCl）和催化量的2,2,6,6-四甲基哌啶（TMP-H）结合而去质子化。在具有NHC配体（IPr）的镍催化剂存在下，金属化的3-己基噻吩与2,3-和2,5-二溴噻吩反应，以提供二偶联产物，尽管等摩尔反应，但仅与二溴噻吩的回收一起提供。3-己基噻吩与二溴代苯衍生物的1：1反应也可得到双偶合产物作为唯一产物。
• MODULAR SUPRAMOLECULAR ACTIVE LAYER AND ORGANIC PHOTOVOLTAIC DEVICES
  申请人：UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC.

  公开号：US20140345682A1

  公开（公告）日：2014-11-27

  A photoactive layer for an organic photovoltaic device has a supramolecular assembly of donors or acceptors formed from a plurality of units that are mixed with electron acceptors or electron donors, respectively, to form an ordered or semi-ordered bulk heterojunction structure. Each unit is formed from a plurality of sub-units that are combined and ordered by hydrogen bonding or other non-covalent interactions to form units that by π-stacking and, optionally, other forces are organized into the supramolecular assembly. Each sub-unit includes at least one electron donor or acceptor moiety, at least one non-covalent interacting moiety, and a linking moiety between the non-covalent interacting moiety and the electron donor or electron acceptor moiety of the sub-unit. The organized supramolecular assembly connects donors or acceptors through the thickness of the photoactive layer, and allows parallel continuous electron acceptor or electron donor phases through the thickness of the active layer.

  一种有机光伏器件的光活性层具有供体或受体的超分子组装，由多个单元混合电子受体或电子供体形成有序或半有序的杂化结构。每个单元由多个亚单元组成，通过氢键或其他非共价相互作用组合和有序排列，形成通过π堆积和可选的其他力组织成超分子组装体。每个亚单元包括至少一个电子供体或受体基团，至少一个非共价相互作用基团，以及连接非共价相互作用基团和亚单元电子供体或电子受体基团之间的连接基团。有序的超分子组装体通过光活性层的厚度连接供体或受体，并允许平行连续的电子受体或电子供体相通过活性层的厚度。
• A BODIPY-based highly emissive dye with thiophene-based branch harvesting the light
  作者：Xiaochuan Li、Yujie Han、Myeong Jin Kim、Young-A Son

  DOI：10.1080/15421406.2018.1467613

  日期：2018.2.11

  A novel BODIPY-based dye with highly emissive character was configured by Sonogashira coupling and routinely characterized by NMR and MS technology. The emission of dye was investigated in solution/film/solid and shows intensive emission. In solution, the emission peak appeared around 510nm with little influence by the polar environment. The terthiophene plays an effective antenna effect, harvesting the light and transferring the energy to BODIPY. The pseudo Stoke's shift enlarged to approximate to 170nm in solution. In film, the emission peak shifted to 563nm in polycarbonate matrix. And it shifted further to 585nm in solid due to the highly twisted structure, which avoided closely regular-tight packing. The dye rendered an intense fluorescence, good optothermal stability, and high fluorescence quantum yield (0.55). The solid emission showed highly red emission with Commission Internationale de L'Eclairage (CIE) coordinates of (X = 0.69, Y = 0.31). Thus, the synthesized dye is idea candidate for emitting materials.
• Thiophene Modulated BODIPY Dye as a Light Harvester
  作者：Xiaochuan Li、Meifei Liao、Jia Sun、Gisu Heo、Young-A Son

  DOI：10.1080/15421406.2019.1597557

  日期：2019.1.22

  A new BODIPY dye with terthiophene branched is configured by Sonogashira coupling and fully characterized by NMR and MS. In general organic solvents, it emits typical green fluorescence ranging in 513-518 nm, like most BODIPY analogues. The terthiophene substitution is greatly improved and the emission peak does not sensitive to the polarity environment. More importantly, the terthiophene plays the role of antenna, harvesting the 340 nm's excitation energy and transferring the energy to BODIPY efficiently. Even though the molar extinction coefficient in 340 nm is lower than that of maximum absorption, it can enlarge the pseudo Stoke's shift to similar to 170 nm, well separating the excitation and emission. In film, the emission shifted to 562 nm due to the polymer chain dissipation part of the energy. It shifted further to 585 nm in solid. The branched terthiophene configures a twisted molecular conformation, which avoids the dye regular packing. Highly emission, excellent solubility and stability constitute the general character of the thiophene attached BIDIPY dye.
• Tetrathiophenes with thiophene side chains: effect of substitution on packing and conjugation
  作者：Geeta Saini、Nigel T. Lucas、Josemon Jacob

  DOI：10.1016/j.tetlet.2010.03.087

  日期：2010.6

  The effect of substitution pattern on conjugation and packing has been investigated by synthesizing a series of tetrathiophenes with systematically varied alkyl thiophene substituents. (C) 2010 Elsevier Ltd. All rights reserved.