5-(diethylamino)thiophene-2-carboxaldehyde | 51082-93-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(diethylamino)thiophene-2-carboxaldehyde
• 英文别名: 5-(Diethylamino)thiophene-2-carbaldehyde
• CAS: 51082-93-0
• 化学式: C₉H₁₃NOS
• 分子量: 183.274
• InChiKey: IJXNNFZFKQMSPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(diethylamino)thiophene-2-carboxaldehyde 在 正丁基锂 、 potassium tert-butylate 作用下， 生成 2-[[2-[(E)-2-[5-(diethylamino)thiophen-2-yl]ethenyl]-1,3-thiazol-5-yl]methylidene]propanedinitrile
  参考文献：
  名称：

  Synthesis of nonlinear optical chromophores containing electron-excessive and -deficient heterocyclic bridges. The auxiliary donor–acceptor effects

  摘要：

  合成了具有噻唑和噻吩环及夹杂乙烯单元作为π-共轭桥的推拉取代非线性光学染料。讨论了杂环的性质和位置对染料电荷转移跃迁能量的影响。

  DOI：

  10.1039/a708689j
• 作为产物：
  描述：

  5-溴噻吩-2-甲醛 、 二乙胺 在 对甲苯磺酸 作用下， 反应 24.0h， 生成 5-(diethylamino)thiophene-2-carboxaldehyde
  参考文献：
  名称：

  ATOP 染料。用于光折变材料中高折射率调制的多功能部花青发色团的优化

  摘要：

  本文报道了氨基-噻吩基-二氧氰基-吡啶 (ATOP) 发色团的合成、表征和结构优化，以制备具有前所未有的光折变性能的多功能无定形材料。ATOP 发色团的结构（动态 NMR、XRD）和电子（UV/vis、电光吸收、克尔效应测量）表征揭示了花青型 pi 共轭系统，具有强而窄的吸收带（epsilon(max) = 140 000 L mol(-)(1) cm(-)(1))，高极化率各向异性（deltaalpha(0) = 55 x 10(-)(40) CV(-)(1) m(2)），和大偶极矩 (13 D)。这种分子电子特性的组合是在具有低玻璃化转变温度 (T(g)) 的光折变材料中产生强电光响应的先决条件。其他重要的材料相关特性，例如与光电导聚（N-乙烯基咔唑）（PVK）主体基质的相容性、低熔点、低 T(g) 和成膜能力，通过连接到的四种不同烷基取代基的变化进行了优化。 ATOP 核心。含有 40

  DOI：

  10.1021/ja002321g

文献信息

• Amino(oligo)thiophene-Based Environmentally Sensitive Biomembrane Chromophores
  作者：Ping Yan、Aifang Xie、Meide Wei、Leslie M. Loew

  DOI：10.1021/jo800852h

  日期：2008.9.1

  carboxaldehyde. Side chains on these fluorophores impart a strong affinity for biological membranes. Compared with benzene analogues, these thiophene fluorophores show significant red shift in the absorption and emission spectra, offering compact red and near-infrared emitting fluorophores. More importantly, both the fluorescence quantum yields and the emission peaks are very sensitive to various environmental

  越来越需要使用荧光探针进行细胞成像，荧光探针发射更长的波长，以最大限度地减少生物组织的吸收、自发荧光和散射的影响。在本文中，通过 4-甲基吡啶鎓盐和各种氨基（低聚）噻吩甲醛之间的羟醛缩合，合成了一系列以氨基（低聚）噻吩供体为特征的新型环境敏感半花青染料，而后者又是从溴的胺化中获得的。 (低聚)噻吩甲醛。这些荧光团上的侧链赋予生物膜很强的亲和力。与苯类似物相比，这些噻吩荧光团在吸收和发射光谱中显示出显着的红移，提供紧凑的红色和近红外发射荧光团。更重要的是，荧光量子产率和发射峰对各种环境因素都非常敏感，例如溶剂极性或粘度、膜电位和膜组成。这些发色团还表现出很强的非线性光学特性，包括双光子荧光和二次谐波产生，它们本身对环境敏感。长波长荧光和非线性光学特性的结合使这些发色团非常适合需要在组织深处进行传感或成像的应用。它们本身对环境敏感。长波长荧光和非线性光学特性的结合使这些发色团非常适合需要在组织
• Amino(oligo)thiophene dyes, preparation thereof, and optical methods of use
  申请人：The University of Connecticut

  公开号：US08129532B2

  公开（公告）日：2012-03-06

  Amino(oligo)thiophene dyes useful for studying the electrophysiology of organelles, cells, and tissues are described. Compared to previously known dyes, the amino(oligo)thiophene dyes exhibit improved (faster) response to membrane potential changes, as well as the ability to be excited by 1064 nanometer femtosecond pulses. Methods of preparing the amino( oligo )thiophene dyes are also described.

  描述了用于研究细胞器、细胞和组织电生理学的氨基（寡）噻吩染料。与先前已知的染料相比，氨基（寡）噻吩染料表现出对膜电位变化的改善（更快）响应，以及能够被1064纳米飞秒脉冲激发的能力。还描述了制备氨基（寡）噻吩染料的方法。
• AMINO(OLIGO)THIOPHENE DYES, PREPARATION THEREOF, AND OPTICAL METHODS OF USE
  申请人：Loew Leslie M.

  公开号：US20090042227A1

  公开（公告）日：2009-02-12

  Amino(oligo)thiophene dyes useful for studying the electrophysiology of organelles, cells, and tissues are described. Compared to previously known dyes, the amino(oligo)thiophene dyes exhibit improved (faster) response to membrane potential changes, as well as the ability to be excited by 1064 nanometer femtosecond pulses. Methods of preparing the amino(oligo)thiophene dyes are also described.

  描述了用于研究细胞器、细胞和组织电生理学的氨基(寡聚)噻吩染料。与先前已知的染料相比，氨基(寡聚)噻吩染料对膜电位变化的响应更快，并且能够受到1064纳米飞秒脉冲的激发。还描述了制备氨基(寡聚)噻吩染料的方法。
• Tunable spectroscopic and electrochemical properties of conjugated push–push, push–pull and pull–pull thiopheno azomethines
  作者：Stéphane Dufresne、Marie Bourgeaux、W. G. Skene

  DOI：10.1039/b616379c

  日期：——

  Novel azomethines consisting uniquely of thiophene units were examined. The highly conjugated compounds were prepared by condensing air stable aminothiophenes with 2-thiophene aldehydes, which were substituted with various electronic groups. The resulting azomethines are highly conjugated and are both reductively and hydrolytically resistant. Various electron donating and accepting groups placed in the 2-position of 5-thiophene carboxaldehyde lead to electronically delocalized push–push, pull–pull, and push–pullazomethines. These electronic groups affect both the HOMO and the LUMO levels, which influence the absorption and emission spectra. Colors spanning the entire visible spectrum ranging from yellow to blue are possible with these nitrogen containing conjugated compounds. Excited state deactivation of the singlet excited state occurs predominately by internal conversion while only a small amount of energy is dissipated by intersystem crossing to the triplet state and by fluorescence. The ensuing fluorescence and phosphorescence of the thiopheno azomethines are similar to those of their thiophene analogues currently used in functional devices, but with the advantage of a low triplet state and tunable HOMO–LUMO energy levels extending from 3.0 to 1.9 eV. Quasi-reversible electrochemical radical cation formation is possible while the oxidation potential is dependent on the nature of the electronic group appended to the thiophene. The crystallographic data of the electronic push–push system show the azomethine bonds are planar and linear and they adopt the E isomer.

  我们研究了仅由噻吩单元组成的新型偶氮甲烷。这些高度共轭的化合物是通过将空气稳定的氨基噻吩与 2-噻吩醛缩合而制备的，后者被各种电子基团取代。所制备的偶氮甲烷具有高度共轭性，并具有抗还原性和抗水解性。在 5-噻吩醛的 2 位上放置了各种电子供体和受体，从而产生了电子分散的推推、拉拉和推拉偶氮甲烷。这些电子基团会影响 HOMO 和 LUMO 水平，从而影响吸收和发射光谱。这些含氮共轭化合物的颜色横跨从黄色到蓝色的整个可见光谱。单重激发态的激发态失活主要是通过内部转换实现的，只有少量能量是通过系统间转换到三重态和荧光而耗散的。噻吩偶氮甲烷随之产生的荧光和磷光与目前用于功能器件的噻吩类似物相似，但其优点是三重态较低，HOMOâLUMO 能级可调，从 3.0 到 1.9 eV。这种化合物可以形成准可逆的电化学自由基阳离子，而氧化电位则取决于噻吩所附电子基团的性质。电子推挽系统的晶体学数据显示，偶氮甲基键是平面和线性的，它们采用 E 异构体。
• Synthesis of novel sulfonyl-substituted pyrrole chromophores for second-order nonlinear optics
  作者：Shang-Shing P Chou、Yu-Hsin Yeh

  DOI：10.1016/s0040-4039(00)02232-2

  日期：2001.2

  The first synthesis of sulfonyl-substituted pyrrole chromophores 1–4 and their UV–vis absorptions, second-order nonlinear optical properties and thermal stability are described and compared with those of the benzene, thiophene and furan analogues 5–9.

  磺酰基取代吡咯发色团的第一合成1 - 4和它们的UV-VIS吸收，二阶非线性光学性质和热稳定性进行说明，并与那些在苯，噻吩和呋喃类似物5 - 9。