5-formyl-5'-(4-N,N-diethylaminophenyl)-2,2'-bithiophene | 696645-47-3

• 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-formyl-5'-(4-N,N-diethylaminophenyl)-2,2'-bithiophene
• 英文别名: 5-[5-[4-(diethylamino)phenyl]thiophen-2-yl]thiophene-2-carbaldehyde
• CAS: 696645-47-3
• 化学式: C₁₉H₁₉NOS₂
• 分子量: 341.498
• InChiKey: ZEJVDJQJGDZXGS-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160 °C
• 沸点：
  504.9±50.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-formyl-5'-(4-N,N-diethylaminophenyl)-2,2'-bithiophene 在 aldehyde dehydrogenase 作用下， 生成
  参考文献：
  名称：

  噻吩桥接醛（TBA）通过调节分子内电荷转移来成像细胞中的ALDH活性

  摘要：

  醛脱氢酶（ALDHs）催化醛氧化为羧酸，并与多种疾病的病因有关。然而，尽管它们很重要，但由于缺少荧光成像探针，在细胞中对ALDH活性进行成像仍具有挑战性。在这份报告中，我们提出了一个新的荧光探针家族，该探针由一个寡聚噻吩和一个侧翼醛与一个电子供体组成，该噻吩被称为噻吩-桥连醛（TBA），可以成像细胞中的ALDH活性。TBAs通过以下方式显示ALDH活性一种基于分子内电荷转移（ICT）调制的荧光传感机制，这使得TBA及其ALDH介导的氧化产物，噻吩桥接的羧酸盐（TBC）具有独特的荧光光谱。在这里，我们显示TBA可以通过以下方式对细胞中的ALDH活性进行成像荧光显微镜，流式细胞仪和酶标仪。使用TBA，我们能够首次针对ALDH抑制剂开发基于细胞的高通量测定方法，并针对A549细胞筛选了一个大型的1460条目亲电试剂库。我们确定了α，β-取代的丙烯酰胺为有效的亲电子片段，可以抑制细胞中ALDH的活

  DOI：

  10.1039/c7sc03017g
• 作为产物：
  描述：

  4-(diethylamino)phenylboronic acid 、 5-溴-2,2'-联噻吩-5'-甲醛 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以35%的产率得到5-formyl-5'-(4-N,N-diethylaminophenyl)-2,2'-bithiophene
  参考文献：
  名称：

  Multifunctional fluorescent probe for effective visualization, inhibition, and detoxification of β-amyloid aggregation via covalent binding

  摘要：

  构建了一种多功能反应性荧光探针DTB，用于β-淀粉样蛋白的生物传感、聚集抑制和毒性缓解。

  DOI：

  10.1039/d2cc00318j

文献信息

• Synthesis of 5-aryl-5′-formyl-2,2′-bithiophenes as new precursors for nonlinear optical (NLO) materials
  作者：Cyril Herbivo、Alain Comel、G. Kirsch、M. Manuela M. Raposo

  DOI：10.1016/j.tet.2008.12.078

  日期：2009.3

  A series of formyl-substituted 5-aryl-2,2′-bithiophenes 5 were synthesized using two different methods: Vilsmeier–Haack–Arnold reaction (VHA) or through Suzuki coupling. The synthesis of compounds 5 through the Vilsmeier–Haack–Arnold reaction, starting from inexpensive and easily available precursors such as acetophenones, gave the title compounds in low yields after four reaction steps. On the other

  使用两种不同的方法：Vilsmeier–Haack–Arnold反应（VHA）或通过Suzuki偶联合成了一系列被甲酰基取代的5-芳基-2,2'-联噻吩5。通过Vilsmeier-Haack-Arnold反应进行的化合物5的合成，是从廉价且容易获得的前体（如苯乙酮）开始的，经过四个反应步骤后，标题化合物的收率很低。另一方面，官能化的芳基硼酸7和5-溴-5'-甲酰基-2,2'-联噻吩6的Suzuki偶联仅一步就得到了高产率的化合物5。
• Fluorescence and two-photon absorption of push—pull aryl(bi)thiophenes: structure—property relationships
  作者：Emilie Genin、Vincent Hugues、Guillaume Clermont、Cyril Herbivo、M. Cidália R. Castro、Alain Comel、M. Manuela M. Raposo、Mireille Blanchard-Desce

  DOI：10.1039/c2pp25258a

  日期：2012.11

  Photophysical and TPA properties of series of push—pull aryl(bi)thiophene chromophores bearing electron-donating (D) and electron-withdrawing (A) end-groups of increasing strength are presented. All compounds show an intense intramolecular charge transfer (ICT) absorption band in the visible region. Increasing the D and/or A strength as well as the length of the conjugated path induces bathochromic and hyperchromic shifts of the absorption band as reported for analogous push—pull polyenes. Yet, in contrast with corresponding push—pull polyenes, a significant increase in fluorescence is observed. In particular, chromophores built from a phenyl—bithienyl conjugated path and bearing strong D and A end-groups were found to combine very large one and two-photon brightness as well as strong emission in the red/NIR region. These molecules hold promise as biphotonic fluorescent probes for bioimaging.

  本文介绍了一系列推拉芳基（双）噻吩发色团的光物理和 TPA 特性，这些发色团带有电子捐赠（D）和电子撤回（A）端基，其强度不断增加。所有化合物在可见光区域都显示出强烈的分子内电荷转移（ICT）吸收带。增加 D 和/或 A 的强度以及共轭路径的长度会引起吸收带的浴色和高色移，这与类似推挽多烯的情况相同。然而，与相应的推拉式多烯相比，荧光显著增加。特别是，由苯基-双噻吩共轭路径和带有强 D 和 A 端基的发色团被发现结合了非常大的单光子和双光子亮度，以及在红色/近红外区域的强发射。这些分子有望成为用于生物成像的双光子荧光探针。
• Theoretical and experimental studies of aryl-bithiophene based push-pull π-conjugated heterocyclic systems bearing cyanoacetic or rhodanine-3-acetic acid acceptors for SHG nonlinear optical applications
  作者：Sara S.M. Fernandes、Cyril Herbivo、João Aires-de-Sousa、Alain Comel、Michael Belsley、M. Manuela M. Raposo

  DOI：10.1016/j.dyepig.2017.10.001

  日期：2018.2

  understand how structural modifications influence the electronic, linear and nonlinear optical properties. The push-pull conjugated chromophores 2–3 bear a bithiophene spacer conjugated with a phenyl ring functionalized with N,N-dialkylamino electron-donor groups together with cyanoacetic or rhodanine-3-acetic acid acceptor groups. Theoretical (DFT calculations) and experimental studies were carried

  设计并合成了一系列基于推挽式芳基-联噻吩的系统2–3，以了解结构修饰如何影响电子，线性和非线性光学性质。推挽共轭生色团2-3带有联噻吩间隔基，该间隔基与被N，N-二烷基氨基电子给体基团以及氰基乙酸或Rhodanine-3-乙酸受体基团官能化的苯环共轭。进行了理论（DFT计算）和实验研究，以获取有关推挽联噻吩衍生物的构象，电子结构，电子分布，偶极矩和分子非线性响应的信息。这项多学科研究表明，发色团2e 由于N，N-二甲基氨基的强大的电子给体能力，乙炔连接基表现出最高的超极化率β（10440×10 -30 esu），并且乙炔连接基不仅延长了π-共轭路径，而且赋予了较小的畸变系统。
• Synthesis and characterization of novel, thermally stable 2-aryl-5-dicyanovinylthiophenes and 5-aryl-5′-dicyanovinyl-2,2′-bithiophenes as potentially promising non-linear optical materials
  作者：Cyril Herbivo、Alain Comel、G. Kirsch、A. Maurício C. Fonseca、M. Belsley、M. Manuela M. Raposo

  DOI：10.1016/j.dyepig.2010.01.006

  日期：2010.8

  Two series of dicyanovinyl-substituted compounds namely 2-aryl-5-dicyanovinylthiophenes and 5-aryl-5'-dicyanovinyl-2,2'-bithiophenes were synthesized through Knoevenagel condensation of the corresponding 2-aryl-5-formyl-thiophenes and 5-aryl-5'-formyl-2,2'-bithiophene precursors. In contrast, the 2-aryl-5-formyl-thiophenes precursor were prepared through the Vilsmeier Haack Arnold reaction starting from inexpensive and easily available precursors such as acetophenones; this method produced the title compounds in higher yield than that recently reported which involved the Suzuki coupling of functionalized aryl boronic acids with 5-bromo-2-formyl-thiophene. Electrochemical studies and characterization of both the linear and non-linear optical properties and thermal properties indicated that good non-linearity was complemented by exceptional thermal stability for some chromophores, making them potential candidates for several optoelectronic applications such as solvatochromic probes and non-linear optical materials. (C) 2010 Elsevier Ltd. All rights reserved.
• Multifunctional fluorescent probe for effective visualization, inhibition, and detoxification of β-amyloid aggregation <i>via</i> covalent binding
  作者：Ziqi Zhang、Yue Cao、Qiong Yuan、Chenghui Liu、Xinrui Duan、Yanli Tang

  DOI：10.1039/d2cc00318j

  日期：——

  A multifunctional reactive fluorescent probe DTB was constructed for biosensing, aggregation inhibition, and toxicity alleviation of β-amyloid.

  构建了一种多功能反应性荧光探针DTB，用于β-淀粉样蛋白的生物传感、聚集抑制和毒性缓解。