2,5-bis(2-thienyl)thiophene-S,S-dioxide | 211737-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,5-bis(2-thienyl)thiophene-S,S-dioxide
• 英文别名: [2,2':5',2''-terthiophene] 1',1'-dioxide；2,2':5',2''-Terthiophene, 1',1'-dioxide；2,5-dithiophen-2-ylthiophene 1,1-dioxide
• CAS: 211737-44-9
• 化学式: C₁₂H₈O₂S₃
• 分子量: 280.392
• InChiKey: RYDHSGKWZKJTKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,5-diiodothiophene-1,1-dioxide 、 噻吩-2-硼酸频哪醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium fluoride 作用下， 生成 2,5-bis(2-thienyl)thiophene-S,S-dioxide
  参考文献：
  名称：

  通过Suzuki偶联进行无溶剂微波辅助的噻吩低聚物合成。

  摘要：

  这项研究的目的是获得一种快速，高效和环保的方法来合成高纯度的噻吩低聚物。噻吩基硼酸和酯与噻吩基溴的无溶剂微波辅助偶联，使用氧化铝作为固体载体，使我们能够快速检查反应时间，温度，催化剂和碱的变化趋势，并轻松优化实验获得公允价值目标产品的条件。该方法为制备可溶性噻吩低聚物提供了新颖，通用且非常快速的途径。因此，例如，通过2-溴-2,2'-联噻吩与双（频哪醇）二硼的反应，在6分钟内获得了四噻吩（分离产率为65％），而二噻吩并噻吩与噻吩基硼酸的反应在11分钟内获得了喹噻吩（分离产率为74％）。报道了新的手性2，2′-联噻吩的合成。对某些反应副产物的详细分析使我们能够阐明反应机理的几个方面。虽然证明使用微波非常方便常规噻吩基部分之间的偶联，但对于噻吩基环与噻吩基-S，S-二氧化物部分的偶联而言却并非如此。实际上，在这种情况下，由于竞争性的，加速的Diels-Alder反应可提供多种缩合产物，因此以低

  DOI：

  10.1021/jo026269d

文献信息

• Synthesis of Thiophene 1,1-Dioxides and Tuning Their Optoelectronic Properties
  作者：Chia-Hua Tsai、Danielle N. Chirdon、Andrew B. Maurer、Stefan Bernhard、Kevin J. T. Noonan

  DOI：10.1021/ol4024024

  日期：2013.10.18

  A 2,5-bis(tributylstannyl)thiophene 1,1-dioxide was prepared from 2,5-bis(trimethylsilyl)thiophene 1,1-dioxide, bis(tributyltin) oxide, and tetrabutylammonium fluoride (TBAF). The 2,5-bis(tributylstannyl)thiophene 1,1-dioxide and a 2,5-diiodothiophene 1,1-dioxide were utilized in a series of Stille cross-coupling reactions to afford thiophene 1,1-dioxides with either electron-donating or electron-withdrawing

  由2，5-双（三甲基甲硅烷基）噻吩1，1-二氧化物，双（三丁基锡）氧化物和四丁基氟化铵（TBAF）制备2，5-双（三丁基锡烷基）噻吩1，1-二氧化物。2,5-双（三丁基锡烷基）噻吩1,1-二氧化物和2,5-二碘噻吩1,1-二氧化物用于一系列的Stille交叉偶联反应中，从而得到具有电子或给体或吸电子的取代基。吸电子基团极大地促进了这些砜杂环的还原，与具有两个苯基的噻吩1,1-二氧化物相比，–C 6 H 4 - p -NO 2取代基产生510 mV的位移。
• Molecular compositions, materials, and methods for efficient multiple exciton generation
  申请人：THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK

  公开号：US10636974B2

  公开（公告）日：2020-04-28

  Embodiments of the present invention provides compounds, compositions, and methods for their preparation that provide efficient intramolecular fission, such that local order and strong nearest neighbor coupling is no longer a design constraint. Inventive materials include organic oligomers and polymers designed to exhibit strong intrachain donor-acceptor interactions and provide intramolecular singlet fission, whereby triplet populations can be generated in very high yields of, e.g., 170% or more. The inventive disclosure is directed to polymers of the general formula: [SA-SD]n with a strong electron acceptor (SA), a strong electron donor (SD), and n a positive integer equal to or greater than two; methods for their preparation and monomers used therein, blends, mixtures and formulations containing them; the use of the polymers, blends, mixtures and formulations as semiconductors in organic electronic (OE) devices, especially in organic photovoltaic (OPV) devices, and to OE and OPV devices comprising these polymers, blends, mixtures or formulations.

  本发明的实施方案提供了可提供高效分子内裂变的化合物、组合物及其制备方法，从而使局部有序和强近邻耦合不再是设计上的限制因素。本发明的材料包括有机低聚物和聚合物，其设计旨在表现出强链内供体-受体相互作用，并提供分子内单子裂变，从而以极高的产率（例如 170% 或更高）产生三重子群。本发明公开了通式聚合物：[SA-SD]n，其中有一个强电子受体（SA），一个强电子供体（SD），n 为等于或大于二的正整数；其制备方法和其中使用的单体，含有它们的共混物、混合物和制剂；这些聚合物、共混物、混合物和制剂在有机电子（OE）器件中作为半导体的用途，特别是在有机光伏（OPV）器件中的用途，以及包含这些聚合物、共混物、混合物或制剂的 OE 和 OPV 器件。
• Facilitated synthesis of functional oligothiophenes for application in thin film devices and live cell imaging
  作者：Francesca DiMaria、Giovanna Barbarella

  DOI：10.1080/17415993.2013.807810

  日期：2013.12.1

  This paper describes recent developments in the synthesis of ultrapure functional oligothiophene-based materials taking advantage of enabling techniques such as microwave/ultrasound irradiation and chitosan-supported palladium catalysts. Examples showing how ultrapure oligothiophenes self-organize in order to optimize charge transport in thin film devices and fluorescence emission inside living cells are reported.[GRAPHICS].
• Oligothiophene <i>S</i>,<i>S</i>-Dioxides. Synthesis and Electronic Properties in Relation to the Parent Oligothiophenes
  作者：G. Barbarella、L. Favaretto、G. Sotgiu、M. Zambianchi、L. Antolini、O. Pudova、A. Bongini

  DOI：10.1021/jo980507g

  日期：1998.8.1

  Oligothiophene S,S-dioxides from dimers to pentamers were obtained in good yields by reaction of mono- and dibrominated thiophene S,S-dioxides with the appropriate thienyl stannanes in the presence of Pd(AsPh3)(4) generated in situ. The reaction rate with brominated thiophene S,S-dioxides is greatly accelerated compared to that employing thienyl bromides to obtain the parent oligothiophenes. HF/6-31G* ab initio calculations on 2,2'-bithiophene and the corresponding mono- and bis-S,S-dioxides show that the functionalization of the thienyl sulfur to the S,S-dioxide does not affect the pi,pi* nature of the frontier orbitals, decreases the energy of the LUMO much more than that of the HOMO, increases the degree of planarity of the molecular skeleton, and leads to higher syn anti rotation barriers about the carbon-carbon bond.
• MOLECULAR COMPOSITIONS, MATERIALS, AND METHODS FOR EFFICIENT MULTIPLE EXCITION GENERATION
  申请人：THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK

  公开号：US20170141318A1

  公开（公告）日：2017-05-18

  Embodiments of the present invention provides compounds, compositions, and methods for their preparation that provide efficient intramolecular fission, such that local order and strong nearest neighbor coupling is no longer a design constraint. Inventive materials include organic oligomers and polymers designed to exhibit strong intrachain donor-acceptor interactions and provide intramolecular singlet fission, whereby triplet populations can be generated in very high yields of, e.g., 170% or more. The inventive disclosure is directed to polymers of the general formula: [SA-SD]n with a strong electron acceptor (SA), a strong electron donor (SD), and n a positive integer equal to or greater than two; methods for their preparation and monomers used therein, blends, mixtures and formulations containing them; the use of the polymers, blends, mixtures and formulations as semiconductors in organic electronic (OE) devices, especially in organic photovoltaic (OPV) devices, and to OE and OPV devices comprising these polymers, blends, mixtures or formulations.