3,3''-二己基-2,2'：5'，2''-对噻吩 | 135831-08-2

• 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: 3,3''-二己基-2,2'：5'，2''-对噻吩
• 英文名称: 3,3''-dihexyl-2,2':5',2''-terthiophene
• 英文别名: 2,5-bis(3-hexylthiophen-2-yl)thiophene
• CAS: 135831-08-2
• 化学式: C₂₄H₃₂S₃
• 分子量: 416.716
• InChiKey: MSQDJEYNQBAYOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3,3''-二己基-2,2'：5'，2''-对噻吩 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以92%的产率得到2,6-二溴-4,8-​​双-（2-乙基己氧基）苯并[1,2-b;4,5-b']二噻吩
  参考文献：
  名称：

  可溶性低带隙低聚噻吩-[all] -S，S-二氧化物基共轭低聚物和聚合物的合成与表征

  摘要：

  可溶性oligothiophene-的一个新家族的合成和表征小号，小号-dioxides以及它们作为积木形成polythiophene-使用小号，小号通过微波辅助Stille偶联聚合描述-dioxides。将砜基团并入聚噻吩主链中会导致聚合物带隙变窄，同时聚噻吩S，S和相对于聚噻吩，二氧化物的含量更低，这种趋势对于最低的未占据分子轨道要比最高的占据分子轨道强得多，从而导致更大的电子接受能力。©2011 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2011年

  DOI：

  10.1002/pola.24641
• 作为产物：
  描述：

  2,6-二溴-4,8-​​双-（2-乙基己氧基）苯并[1,2-b;4,5-b']二噻吩 以1%的产率得到
  参考文献：
  名称：

  Sato Masa-aki, Hiroi Masao, Chem. Lett, (1994) N 6, S 985-988

  摘要：

  DOI：

文献信息

• Molecular engineering of face-on oriented dopant-free hole transporting material for perovskite solar cells with 19% PCE
  作者：Kasparas Rakstys、Sanghyun Paek、Peng Gao、Paul Gratia、Tomasz Marszalek、Giulia Grancini、Kyung Taek Cho、Kristijonas Genevicius、Vygintas Jankauskas、Wojciech Pisula、Mohammad Khaja Nazeeruddin

  DOI：10.1039/c7ta01718a

  日期：——

  Through judicious molecular engineering, novel dopant-free star-shaped D–π–A type hole transporting materials coded KR355, KR321, and KR353 were systematically designed, synthesized and characterized. KR321 has been revealed to form a particular face-on organization on perovskite films favoring vertical charge carrier transport and for the first time, we show that this particular molecular stacking

  通过明智的分子工程，系统地设计，合成和表征了新型无掺杂星形D–π–A型空穴传输材料，其编码为KR355，KR321和KR353。已经发现KR321在钙钛矿薄膜上形成了一个特定的面朝上的组织，这有利于垂直电荷载流子的传输，并且我们首次证明了这种特殊的分子堆叠功能与混合钙钛矿组合使用时可导致功率转换效率超过19％（ FAPbI 3）0.85（MAPbBr 3）0.15。使用没有任何化学添加剂或掺杂的原始空穴传输层获得的19％的效率是最高的，这证明了平面施主核，π间隔基和外围受体的分子工程学导致了高迁移率，并且该设计提供了对以下方面的有用见解用于钙钛矿太阳能电池和光电应用的下一代HTM的合成。
• Effect of the π-linker on the performance of organic photovoltaic devices based on push–pull D–π–A molecules
  作者：Hong Chul Lim、Jang-Joo Kim、Jyongsik Jang、Jong-In Hong

  DOI：10.1039/c8nj00915e

  日期：——

  Two push–pull D–π–A molecules, 3T and DTT as donor materials, were synthesized and characterized for solution-processed bulk heterojunction (BHJ) organic photovoltaic (OPV) devices. The π-linker plays a vital role not only in electrochemical and thermal properties but also affects the thin film morphology of 3T and DTT. 3T showed the high electrochemical stability with a faster electrode reaction rate

  合成了两个推挽式D–π–A分子，即3T和DTT作为供体材料，并对其进行了固溶异质结（BHJ）有机光伏（OPV）器件的表征。π-连接基不仅在电化学和热学性质方面起着至关重要的作用，而且还影响3T和DTT的薄膜形态。3T表现出较高的电化学稳定性，电极反应速度更快。基于3T的固溶处理的OPV器件比基于DTT的器件具有更高的功率转换效率，因为它具有出色的电化学性能。
• Approaching the Integer‐Charge Transfer Regime in Molecularly Doped Oligothiophenes by Efficient Decarboxylative Cross‐Coupling
  作者：Jiang Tian Liu、Hannes Hase、Sarah Taylor、Ingo Salzmann、Pat Forgione

  DOI：10.1002/anie.201914458

  日期：2020.4.27

  A library of symmetrical linear oligothiophene was prepared employing decarboxylative cross-coupling reaction as the key transformation. Thiophene potassium carboxylate salts were used as cross-coupling partners without the need of co-catalyst, base, or additives. This method demonstrates complete chemoselectivity and is a comprehensive greener approach compared to the existing methods. The modularity

  使用脱羧交叉偶联反应作为关键转化制备了对称的线性低聚噻吩文库。噻吩羧酸钾盐用作交叉偶联伙伴，而无需助催化剂，碱或添加剂。与现有方法相比，该方法显示出完全的化学选择性，是一种更全面的绿色方法。通过制备具有最多10个噻吩重复单元的谨慎的寡聚噻吩，可以证明这种方法的模块化。对称的低聚噻吩是典型的有机半导体，可以通过光谱评估其分子电掺杂随链长的变化。观察到整数电荷转移的低聚噻吩临界长度为10个噻吩单元，
• Electrochemistry and electrogenerated chemiluminescence of thiophene and fluorene oligomers. Benzoyl peroxide as a coreactant for oligomerization of thiophene dimers
  作者：Alexander B. Nepomnyashchii、Robert J. Ono、Dani M. Lyons、Christopher W. Bielawski、Jonathan L. Sessler、Allen J. Bard

  DOI：10.1039/c2sc20263h

  日期：——

  The electrochemical properties of oligomers of thiophene (with number of monomer units, n, from 2 to 12) and fluorene (n = 3 to 7) were investigated. Both sets of oligomers were characterized by the presence of two oxidation and two reduction waves as determined by cyclic voltammetry (CV), with the reversibility of the waves depending on the structural properties of the compounds. The addition or removal of a third electron was found to be difficult relative to the second, a finding shown for conjugated oligomers with chain lengths up to 7 in the case of the fluorenes and up to 12 for the thiophenes. The oligothiophenes showed a larger separation between the electrochemical waves for the same chain length, and also substantial electrogenerated chemiluminescence (ECL) signals, whose intensity increased with oligomer size. In contrast, the ECL intensity of the fluorene oligomers was essentially independent of chain length. The ECL spectra for the thiophene dodecamer were obtained with concentrations as low as 20 pM, a result that reflects a high ECL efficiency, close to that of the well-known ECL standard Ru(bpy)32+. Oligomers were also formed on electrochemical reduction of an appropriately functionalized dimer in the presence of benzoyl peroxide producing a longer wavelength emission (maximum at ∼540 nm) as opposed to the spectrum of the dimer (λem = 390 nm).

  研究了噻吩低聚物（单体单元数n为2至12）和芴低聚物（n为3至7）的电化学性质。通过循环伏安法（CV）测定，这两组低聚物均呈现出两个氧化波和两个还原波，其可逆性取决于化合物的结构特性。相对于第二个电子，发现添加或移除第三个电子较为困难，这一发现对于长度不超过7的芴低聚物和长度不超过12的噻吩低聚物中的共轭低聚物适用。噻吩低聚物在相同链长的情况下展现出更大的电化学波分离，同时呈现出显著的电化学发光（ECL）信号，其强度随低聚物大小的增加而增强。相比之下，芴低聚物的ECL强度基本上与链长无关。噻吩十二聚物的ECL光谱在浓度低至20皮摩尔时获得，这一结果反映了高ECL效率，接近于众所周知的ECL标准物Ru(bpy)32+的效率。在苯甲酰过氧化物的存在下，通过对适当功能化的二聚体进行电化学还原也可以形成低聚物，产生的光发射波长较长（最大值约为540纳米），与二聚体的发射光谱（λem = 390纳米）不同。
• Synthesis and characterization of soluble low-bandgap oligothiophene-[all]-<i>S,S</i> -dioxides-based conjugated oligomers and polymers
  作者：Elizabeth Amir、Kulandaivelu Sivanandan、Justin E. Cochran、John J. Cowart、Sung-Yu Ku、Jung Hwa Seo、Michael L. Chabinyc、Craig J. Hawker

  DOI：10.1002/pola.24641

  日期：2011.5.1

  The synthesis and characterization of a new family of soluble oligothiophene‐S,S‐dioxides and their use as building blocks to form polythiophene‐S,S‐dioxides via microwave‐assisted Stille coupling polymerization are described. Incorporation of the sulfone group into the polythiophene backbone leads to narrowing of the polymer bandgap, and while the energies of both Frontier orbitals in polythiophene‐S

  可溶性oligothiophene-的一个新家族的合成和表征小号，小号-dioxides以及它们作为积木形成polythiophene-使用小号，小号通过微波辅助Stille偶联聚合描述-dioxides。将砜基团并入聚噻吩主链中会导致聚合物带隙变窄，同时聚噻吩S，S和相对于聚噻吩，二氧化物的含量更低，这种趋势对于最低的未占据分子轨道要比最高的占据分子轨道强得多，从而导致更大的电子接受能力。©2011 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2011年