二乙基噻吩-2,6-二溴-3,4-二羧酸酯 | 1041441-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 二乙基噻吩-2,6-二溴-3,4-二羧酸酯
• 英文名称: diethyl 2,5-dibromothiophene-3,4-dicarboxylate
• 英文别名: diethyl thiophene-2,6-dibromo-3,4-dicarboxylate；2,5-dibromo-3,4-diethylcarboxylthiophene；Diethyl 2,5-dibromothiophene-3,4-dicarboxylate
• CAS: 1041441-00-2
• 化学式: C₁₀H₁₀Br₂O₄S
• 分子量: 386.061
• InChiKey: LZAWRJAMRCQDPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二乙基噻吩-2,6-二溴-3,4-二羧酸酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 生成 3,7-bis(10-phenylanthracen-9-yl)thieno[3,2-c:4,5-c']dipyran-1,9-dione
  参考文献：
  名称：

  Structurally simple thienodipyrandione-containing reversible fluorescent switching piezo- and acido-chromic materials

  摘要：

  我们在此报告了一系列接枝于刚性、平面和共轭内环烯丙基内酯（噻吩二吡喃二酮）的蒽/芘衍生物的结构-性能相关性，这些衍生物表现出聚集诱导发射。与典型的乙烯基固态荧光材料不同，刚性噻吩二吡喃二酮分子可以产生更高阶的构象扭转，而且由于羰基的存在，C-H⋯O 相互作用增强了分子间的相互作用，从而提高了热稳定性。TDAn 和 TDAnPh 化合物具有独特的压氟变色特性，其发射颜色可通过研磨和加热进行切换。根据 XRD、DSC 和 NMR 等多种光谱技术，观察到的压电变色发射可归因于从结构结晶（有序）态到无定形（无序）态或反之亦然的相变结果。最独特的是，其中一种蒽衍生物 TDAn 显示出特定的酸性氟致变色，而另一种同系物 TDAnPh 则没有，尽管它们在结构上非常相似。晶体结构分析表明，C-H⋯O、π-π 和 C-H⋯π 等各种次生相互作用在超分子组装过程中都发挥了关键作用，从而显示出如此独特的特征。目前的研究揭示了一类新型刺激响应材料，它们在微环境传感、光学开关和记录方面具有巨大的应用潜力。

  DOI：

  10.1039/c3tc31504e
• 作为产物：
  描述：

  二乙基噻吩-3,4-二羧酸酯 在 溴 作用下， 以 溶剂黄146 为溶剂， 以60%的产率得到二乙基噻吩-2,6-二溴-3,4-二羧酸酯
  参考文献：
  名称：

  A glow in the dark: synthesis and electropolymerization of a novel chemiluminescent terthienyl system

  摘要：

  本文介绍了一种基于噻吩基体系的独特（电）化学发光单体及其相应聚合物的合成和表征，这种聚合物是首例带有哒嗪附属物的电活性化学发光聚合物。

  DOI：

  10.1039/b814258k

文献信息

• Non-classical S-Heteroacenes with <i>o</i> -Quinoidal Conjugation and Open-Shell Diradical Character
  作者：Xueliang Shi、Tullimilli Y. Gopalakrishna、Qing Wang、Chunyan Chi

  DOI：10.1002/chem.201701813

  日期：2017.6.22

  physical properties and chemical reactivities that are very different from classical acenes. X‐ray crystallographic analyses revealed that all acenothiophene derivatives Ph‐AT‐1–Ph‐AT‐3 had an o‐quinoidal π‐conjugation with large bond‐length alternation, whereas the acenodithiophene derivative Ph‐ADT‐3 easily dimerized or reacted with oxygen to form a peroxy‐bridged dimer. The long acenothiophene Ph‐AT‐4

  合成了一系列非经典的S-杂并并显示出与经典的并入非常不同的有趣的物理性质和化学反应性。X射线晶体学分析表明，所有对乙酰噻吩衍生物Ph‐AT‐1 – Ph‐AT‐3都具有邻醌型π共轭，且键长交替较大，而对乙酰二噻吩衍生物Ph‐ADT-3则易于二聚或与之反应。氧形成过氧桥联的二聚体。长对乙酰噻吩Ph‐AT‐4也是高度反应性的 通过实验和理论计算，仔细研究了这些独特性质的起源。长的非经典S-杂蒽的高反应性可以通过其固有的开壳双自由基特性和邻喹啉共轭来解释。
• Synthesis and characterization of three thienopyridazine-based copolymers and their application in OFET
  作者：Chia Juan Lim、Lu Li、Yanlian Lei、Feng Zhou、Bo Wu、Xuyao Liu、Furong Zhu、Beng S. Ong、Xiao Hu、Haibin Su、Siu-Choon Ng

  DOI：10.1016/j.tetlet.2016.02.049

  日期：2016.4

  Three low band gap thienopyridazine-based donor–acceptor conjugated polymers, PDTTPTT, PDTTPBT, and PDTTPBDT were synthesized by the Stille copolymerization of thienopyridazine with thienothiophene, benzodithiophene, and bithiophene, respectively. The optical band gaps of PDTTPTT, PDTTPBT, and PDTTPBDT polymers were determined as 1.41 eV, 1.43 eV, and 1.58 eV, respectively by UV absorption. The deep

  通过噻吩并哒嗪与噻吩并噻吩，苯并二噻吩和联噻吩的斯蒂勒共聚反应，合成了三种低带隙的噻吩并哒嗪基供体-受体共轭聚合物，PDDTTPT，PDDTPPT和PDTTPBDT。通过紫外吸收，PDTTPTT，PDTTTPT和PDTTPBDT聚合物的光学带隙分别确定为1.41 eV，1.43 eV和1.58 eV。通过循环伏安法测定三种聚合物的深HOMO水平。制备了这三种聚合物以形成有机场效应晶体管，并研究了它们作为p型半导体的性能。
• Dominating Antiaromatic Character of <i>as</i>-Indacene Decides Overall Properties of a Formally Aromatic Dicyclopenta[<i>c</i>]fluorenothiophene
  作者：Priyank Kumar Sharma、Dibyendu Mallick、Himanshu Sharma、Soumyajit Das

  DOI：10.1021/acs.orglett.3c00261

  日期：——

  Dicyclopenta[c]fluorenothiophene 5 was synthesized as the isoelectronic polycyclic heteroarene analogue of an as-indacenodifluorene with a (4n + 2)π-electron perimeter. Single-crystal and 1H NMR analyses indicated a quinoidal ground state for 5, which was supported by theoretical calculations while suggesting a degree of antiaromaticity of the as-indacene subunit greater than that for s-indacenodifluorene

  Dicyclopenta[ c ]fluorenothiophene 5被合成为具有 (4 n + 2)π 电子周长的as-茚并二芴的等电子多环杂芳烃类似物。单晶和1 H NMR 分析表明5为醌型基态，这得到理论计算的支持，同时表明as -indacene difurene 3的抗芳香性程度大于s -indacenodifluorene 。5的主要反芳香性由到达近红外区域的宽弱强吸收尾、四级氧化还原两性和小的 HOMO-LUMO 能隙证明。
• Synthesis and properties of a novel redox driven chemiluminescent material built on a terthienyl system
  作者：Nurdan Atılgan、Fatih Algı、Ahmet M. Önal、Atilla Cihaner

  DOI：10.1016/j.tet.2009.05.019

  日期：2009.7

  A novel redox driven chemiluminescent material built on a terthienyl system, namely 5,7-di-ethylenedioxythiophen-2-yl-2,3-dihydro-thieno[3,4-d]pyridazine-1,4-dione (ETE-Lum), which is soluble in both organic media and basic aqueous solution was synthesized and characterized. Furthermore, its polymer, PETE-Lum, which is one of the most rare examples of chemiluminescent polymeric materials bearing a pyridazine unit, was obtained successfully by electrochemical means. Both of the materials give chemiluminescence either by treatment with oxidants (H2O2 and/or KMnO4) or by the application of a potential pulse. (C) 2009 Elsevier Ltd. All rights reserved.
• Electrochromic performance and ion sensitivity of a terthienyl based fluorescent polymer
  作者：Nurdan Atılgan、Atilla Cihaner、Ahmet M. Önal

  DOI：10.1016/j.reactfunctpolym.2009.12.006

  日期：2010.4

  A novel terthienyl based fluorescent polymer bearing strong electron-withdrawing substituents directly attached to the 3,4-positions of the central thiophene ring was synthesized by electrochemical polymerization of diethyl 2,5-di(3,4-ethylenedioxythiophen-2-yl)thiophene-3,4-dicarboxylate. The corresponding polymer was characterized by cyclic voltammetry, FT-IR and UV-vis spectroscopy. The polymer has a well-defined redox process (E-p,E-1/2 = 0.74 V) and demonstrates a reversible electrochromic behavior; lilac in the neutral state and transparent sky blue in the oxidized state. Also, the polymer had low band gap (E-g = 1.82 eV) and high redox stability (retaining 94.0% of its electro-activity after 500th switch). Moreover, the sensitivity of both the monomer and its polymer towards metal cations was investigated by monitoring the change in the fluorescence intensity. Among various common ions both the monomer and its polymer were found to be selective towards Cu2+ and Cu+ ions by quenching the fluorescence efficiency with a Stern-Volmer constant (K-sv) of (1.4-1.6 x 10(3) M-1) and (1.5-1.8 x 10(2) M-1) for monomer and polymer solutions, respectively. (c) 2010 Elsevier Ltd. All rights reserved.