2-硝基-5-噻吩-2-基噻吩 | 34682-89-8

• 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: 2-硝基-5-噻吩-2-基噻吩
• 英文名称: 5-nitro-2,2'-bithiophene
• 英文别名: 2-nitro-5-thiophen-2-ylthiophene
• CAS: 34682-89-8
• 化学式: C₈H₅NO₂S₂
• 分子量: 211.265
• InChiKey: WGSCFRDYMPBHBJ-UHFFFAOYSA-N

物化性质

• 熔点：
  113-113.5 °C
• 沸点：
  338.6±32.0 °C(Predicted)
• 密度：
  1.451±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-硝基-5-噻吩-2-基噻吩 在 溴 作用下， 生成 3,3',4,4',5,5'-hexabromo-2,2'-bithiophene
  参考文献：
  名称：

  Steinkopf; Koehler, Justus Liebigs Annalen der Chemie, 1936, vol. 522, p. 17,26

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2'-联二噻吩 在 硝酸 、 乙酸酐 作用下， 生成 2-硝基-5-噻吩-2-基噻吩
  参考文献：
  名称：

  2,2'-二噻吩基及其部分衍生物的电子吸收光谱研究。分子轨道治疗

  摘要：

  已经研究了 2,2'-二噻吩基及其许多衍生物的电子吸收光谱。从光谱预测主要的构象异构体以及分子的极性。对 5-甲酰基-2,2'-二噻吩基的不同构象异构体进行了分子轨道计算，证明 s-trans 几何结构是该分子的主要构象异构体。在计算和观察到的跃迁能量和强度之间观察到良好的一致性。

  DOI：

  10.1246/bcsj.58.2126

文献信息

• Design, Synthesis, Linear, and Nonlinear Optical Properties of Conjugated (Porphinato)zinc(II)-Based Donor−Acceptor Chromophores Featuring Nitrothiophenyl and Nitrooligothiophenyl Electron-Accepting Moieties
  作者：Tian-Gao Zhang、Yuxia Zhao、Inge Asselberghs、André Persoons、Koen Clays、Michael J. Therien

  DOI：10.1021/ja0402553

  日期：2005.7.13

  wavelengths (lambda(inc)) of 800 and 1300 nm; interestingly, measured beta(1300) values ranged from 650 --> 4350 x 10(-30) esu. The combined linear and nonlinear optical properties of these compounds challenge the classical concept of the nonlinearity/transparency tradeoff in charge-transfer chromophores: the magnitude of the molecular hyperpolarizability is observed to vary substantially despite approximately

  使用涉及[5-溴-15-三异丙基甲硅烷基乙炔基-10,20-二芳基卟吩基]的金属催化交叉偶联反应合成了一系列广泛的基于共轭（卟啉）锌（II）的发色团，这些发色团具有硝基噻吩和硝基低聚噻吩电子接受部分锌 (II) 和不寻常的富含电子的铃木卟啉合成子，[5-(4-二甲氨基苯基乙炔基)-15-(4',4',5',5'-四甲基 [1',3',2'] dioxaborolan-2'-yl)-10,20-diarylporphinato]zinc(II)，具有适当官能化的芳基和噻吩基前体。这些供体-受体发色团具有以 5-硝基封端的苯硫基、[2,2']联苯硫基和 [2,2';5',2'']三联苯单元；一系列结构的特点是这些受体部分直接附加到卟啉大环中间碳位置，而第二组利用中间的中间乙炔基部分来修饰卟啉与噻吩的结合。这些化合物的动态超极化率是通过在 800 和 1300 nm 的基本入射辐射波长 (λ(inc))
• Synthesis of 2-Nitrothiophenes <i>via</i> Tandem Henry Reaction and Nucleophilic Substitution on Sulfur from β-Thiocyanatopropenals
  作者：Lin Rong、Yingxia Shen、Guoxi Xiong、Yuefa Gong

  DOI：10.1002/jhet.3446

  日期：2019.2

  A new synthetic route of 2‐nitrothiophenes was described through a tetra‐n‐butylammonium fluoride‐promoted or diisopropylethylamine‐promoted tandem Henry reaction and nucleophilic substitution of nitromethane with 3‐thiocyanatopropenals, which were conveniently prepared by the replacement reaction of 3‐chloropropenals with potassium thiocyanate under a mild acidic condition.

  通过四正丁基氟化铵促进或二异丙基乙胺促进的串联亨利反应以及用3-硫氰基丙烯醛对硝基甲烷进行亲核取代，描述了一种2-硝基噻吩的新合成路线，该方法可方便地通过将3-氯丙烯醛与在弱酸性条件下的硫氰酸钾。
• Mono(η⁵-cyclopentadienyl)metal(II) Complexes with Thienyl Acetylide Chromophores: Synthesis, Electrochemical Studies, and First Hyperpolarizabilities
  作者：Tiago J. L. Silva、Paulo J. Mendes、Ana M. Santos、M. Helena Garcia、M. Paula Robalo、J. P. Prates Ramalho、A. J. Palace Carvalho、Marina Büchert、Christian Wittenburg、Jürgen Heck

  DOI：10.1021/om4001204

  日期：2014.9.22

  optical properties in these complexes. In this series, the complexity of the push–pull systems is revealed; even so, several trends in the second-order hyperpolarizability can still be recognized. In particular, the overall data seem to indicate that the existence of other electronic transitions in addition to the main MLCT clearly controls the effectiveness of the organometallic donor ability on the second-order

  一系列单（η 5 -环戊二烯基）金属（II）配合物与硝基取代的噻吩基乙炔化通式配位体[M（η 5 -C 5 H ^ 5）（L）（C≡CC 4 H ^ 2 S} ñ NO 2）]（M =铁，L =κ 2 -DPPE，ñ = 1，2; M = RU，L =κ 2 -DPPE，2 PPH 3，ñ = 1，2; M =镍，L = PPh 3，n= 1、2）已合成，并已通过NMR，FT-IR和UV-Vis光谱进行了全面表征。通过循环伏安法研究了配合物的电化学行为。络合物的二次超极化率（β）已通过1500 nm处的超瑞利散射（HRS）测量确定。研究了不同有机金属碎片的供体能力对二次超极化率的影响，并将其与光谱和电化学数据相关联。密度泛函理论（DFT）和时变DFT（TDDFT）计算被用来更好地理解这些配合物中的二阶非线性光学性质。在本系列文章中，揭示了推挽系统的复杂性。即便如此，二阶超极化率的几种趋势仍然可以被认识到。特别是，
• Mono and Dinuclear Palladium Pincer Complexes of NNSe Ligand as a Catalyst for Decarboxylative Direct C−H Heteroarylation of (Hetero)arenes
  作者：Sohan Singh、Vikki N. Shinde、Sunil Kumar、Neha Meena、Nattamai Bhuvanesh、Krishnan Rangan、Anil Kumar、Hemant Joshi

  DOI：10.1002/asia.202300628

  日期：2023.10.4

  NNSe pincer ligand and its palladium pincer complexes. Surprisingly, the reactivity of the ligand toward the palladium precursor is base-dependent. In the presence of the Et3N base, a mononuclear pincer complex was formed whereas in the absence of a base, a dinuclear pincer complex was formed. The complexes were used as catalysts for decarboxylative direct C−H heteroarylation of (hetero)arenes. Among

  本报告描述了新型 NNSe 钳形配体及其钯钳形配合物的合成。令人惊讶的是，配体对钯前体的反应性是碱依赖性的。在存在Et 3 N碱基的情况下，形成单核钳复合物，而在不存在碱基的情况下，形成双核钳复合物。该配合物用作（杂）芳烃脱羧直接 C−H 杂芳基化的催化剂。在这些配合物中，发现双核配合物更具反应性。只需 2.5 mol% 的催化剂负载即可激活广泛的底物范围。
• Synthesis and Solvatochromic Properties of Donor-Acceptor-Substituted Oligothiophenes
  作者：Franz Effenberger、Frank Wuerthner、Felix Steybe

  DOI：10.1021/jo00112a032

  日期：1995.4

  The Pd-catalyzed cross coupling reaction of electron donor-substituted thiophenes 1 with electron acceptor-substituted halothiophenes 2,10 via organozinc intermediates or organotin compounds 5 to give bi-, ter-, and quaterthiophenes 3, 4, 6, 8, 12, 13, and 14 is described. (Dimethylamino)-bithiophenes 8 with acceptor groups of varying reactivity were prepared via 5d in 60-80% yield, whereas bithiophenes 6d,e were obtained as a mixture with phenylthiophenes 7d,e. Symmetrical substituted byproducts 11 were formed in the conversion of 1b with bromothiophenes 10 via organozinc compounds yielding oligothiophenes 6b and 12. The ter- and quaterthiophenes 13 and 14 were isolated in about 50-70% yield. The electronic interactions between donor and acceptor end groups in the conjugated bithiophenes 3, 4, and 8 are expressed in the intensive and markedly solvatochromic CT transitions. The solvatochromic behavior of 3, 4, and 8 was determined by linear regression analyses of absorption maxima in 11 solvents, whereby bithiophene 3d was found to be a very appropriate indicator dye whose absorption wavenumbers ($) over bar nu(max)(3d) in aliphatic and dipolar aprotic and-on consideration of the polarizability correction term d delta-in aromatic and chlorinated solvents excellently correlate with the pi* values defined by Kamlet and Taft.