5′-phenyl[2,2′-bithiophene]-5-carbaldehyde | 106925-87-5

• 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′-phenyl[2,2′-bithiophene]-5-carbaldehyde
• 英文别名: 5-formyl-5'-phenyl-2,2'-bithiophene；5-(5-Phenylthiophen-2-yl)thiophene-2-carbaldehyde
• CAS: 106925-87-5
• 化学式: C₁₅H₁₀OS₂
• 分子量: 270.376
• InChiKey: MPNRETCKPLHKBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5′-phenyl[2,2′-bithiophene]-5-carbaldehyde 在 哌啶 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 7.0h， 生成 (E)-2-cyano-3-(5′-phenyl[2,2′-bithiophen]-5-yl)acrylic acid
  参考文献：
  名称：

  噻吩基有机D–π–A染料作为光动力疗法的强敏剂

  摘要：

  易于获得的基于噻吩的有机D–π–A敏化剂具有很高的光毒性。通过快速合成结构简化的类似物并评估其在光照射下对HeLa细胞的抗肿瘤活性，阐明了光毒性的结构要求。我们的敏化剂通过I型和II型机制破坏了癌细胞。

  DOI：

  10.1002/ejoc.201701019
• 作为产物：
  描述：

  5-醛基-2-噻吩硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 palladium diacetate 、 sodium carbonate 、 三苯基膦 、 silver carbonate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 水 、 乙腈 为溶剂， 反应 26.0h， 生成 5′-phenyl[2,2′-bithiophene]-5-carbaldehyde
  参考文献：
  名称：

  噻吩基有机D–π–A染料作为光动力疗法的强敏剂

  摘要：

  易于获得的基于噻吩的有机D–π–A敏化剂具有很高的光毒性。通过快速合成结构简化的类似物并评估其在光照射下对HeLa细胞的抗肿瘤活性，阐明了光毒性的结构要求。我们的敏化剂通过I型和II型机制破坏了癌细胞。

  DOI：

  10.1002/ejoc.201701019

文献信息

• Pd-catalyzed oxidative cross-coupling between two electron rich heteroarenes
  作者：Chun-Yang He、Zhen Wang、Cai-Zhi Wu、Feng-Ling Qing、Xingang Zhang

  DOI：10.1039/c3sc51278a

  日期：——

  The transition-metal-catalyzed oxidative cross-coupling between two coupling partners with similar structure and electronic characteristics remains a challenge owing to difficulty in suppressing undesired homo-couplings. We herein report a Pd-catalyzed oxidative cross-coupling between two thiophenes under mild reaction conditions. This approach can also be extended to furans. Some notable advantages

  具有相似结构和电子特性的两个偶联配偶之间的过渡金属催化的氧化交叉偶联由于难以抑制不希望的均相偶联而仍然是一个挑战。我们在本文中报道了在温和的反应条件下，两个噻吩之间的Pd催化的氧化交叉偶联。这种方法也可以扩展到呋喃。该反应的一些显着优点在于其合成简单，省去了有毒的锡烷偶联伙伴，并且具有出色的官能团相容性。该协议的特征使其成为构建电子和光电子材料中感兴趣的2,2'-噻吩-噻吩键合的理想策略。
• 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.