diethyl ((5-bromothiophen-2-yl)methyl)phosphonate | 192801-97-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl ((5-bromothiophen-2-yl)methyl)phosphonate
• 英文别名: diethyl [(5-bromothiophene-2-yl)methyl]phosphonate；(5-Bromothiophen-2-ylmethyl)phosphonic acid diethyl ester；2-bromo-5-(diethoxyphosphorylmethyl)thiophene
• CAS: 192801-97-1
• 化学式: C₉H₁₄BrO₃PS
• 分子量: 313.152
• InChiKey: GCLDKJNVWSVLJP-UHFFFAOYSA-N

物化性质

• 沸点：
  372.5±32.0 °C(Predicted)
• 密度：
  1.461±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl ((5-bromothiophen-2-yl)methyl)phosphonate 在 四(三苯基膦)钯 sodium hydride 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 1.33h， 生成 2-(4-N-cetylpyridinium)-2-[5-(dicyanomethanido)thien-2-yl]ethylene
  参考文献：
  名称：

  Facile, Regioselective Synthesis of Highly Solvatochromic Thiophene-Spaced N-Alkylpyridinium Dicyanomethanides for Second-Harmonic Generation

  摘要：

  The facile and clean synthesis of a navel class of highly solvatochromic chromophores 1 is reported. Compounds 1 are push-pull systems containing a negatively charged dicyanomethanide as a donor group and a positively charged N-alkylpyridinium as an acceptor group. The terminal polar functions are spaced by a thiophene-based moiety containing one or two heterocyclic rings and none, one, or two ethylene bridges. Chromophores 1 have been obtained through a general synthetic scheme involving, as the last step, the 100% regioselective alkylation of the precursor bidentate anions 2, where two competing nucleophilic sites, one neutral at the pyridic nitrogen and one anionic at the carbanionic carbon of the dicyanomethanide group, are present. The unprecedented highly regioselective attack of the alkylating agent onto the neutral pyridic nitrogen rather than the highly charged carbanionic carbon has been also confirmed in the case of the intermolecular competition. Multinuclear (C-13 and N-15) NMR spectroscopy has been used to investigate the structure and the extent of intramolecular charge transfer in 1, which are shown to exist in the ground state as highly charge-separated zwitterionic systems. Experimental results are discussed and compared with semiempirical (PM3) computations. The solvatochromic response of compounds 1, among the highest ever reported in the literature for similar systems, candidates this class of compounds as very attractive active components of nonlinear optical materials.

  DOI：

  10.1021/jo970059x
• 作为产物：
  描述：

  2-甲基噻吩 在 azo-type polymerization initiator V-65 1,3-二溴-5,5-二甲基海因 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 diethyl ((5-bromothiophen-2-yl)methyl)phosphonate
  参考文献：
  名称：

  Amino group-containing heterocyclic derivatives and sensitizing dyes for photoelectric conversion containing the heterocyclic derivatives

  摘要：

  它旨在提供新颖的含氨基杂环衍生物，其在可见光区域具有广泛的吸收区，并适用于具有高光电转换效率的光电转换染料的敏化剂，以及使用相同的光电转换材料、光电转换电极和光电转换电池。即，表示为以下一般式（I）并在末端含有氨基的杂环衍生物：其中R1、R2、R4和R5分别独立地表示氢原子或一个或多个取代基的一价有机基；R3表示能够结合到显示半导体特性的无机多孔材料的锚定基团；X表示二价芳香碳氢基团或两个或更多个二价或更高的芳香碳氢基团的组合；Y表示具有硫原子的二价芳香杂环基团；Z表示二价芳香杂环基团、二价芳香碳氢基团、二价不饱和碳氢基团或其组合；m为1至3的整数。

  公开号：

  US08044219B2

文献信息

• Palladium-Catalyzed Cross-Coupling Reaction of a Chiral Ferrocenyl Zinc Reagent with Aromatic Bromides: Application to the Design of Chiral Octupoles­ for Second Harmonic Generation
  作者：Olivier Riant、Victor Mamane、Isabelle Ledoux-Rak、Sandrine Deveau、Joseph Zyss

  DOI：10.1055/s-2003-37355

  日期：——

  Palladium catalyzed cross coupling reaction of a chiral ferrocenylzinc reagent with aryl bromides allowed the introduction of a planary chiral ferrocenyl subunit on an aryl fragment. Using this method, new C3 symmetric chiral architecture bearing organometallic donor-acceptor fragments were assembled starting from a common tris aldehyde precursor. The non- linear optical properties were measured using the Harmonic Light Scattering method and the potentiality for the new chromophores to behave as octupoles is also discussed.

  钯催化的手性二茂铁基锌试剂与芳基溴的交叉偶联反应，使得二茂铁基片段以平面对称手性方式引入芳基骨架。利用这种方法，从一种常见的三醛前体开始，组装了具有有机金属供体-受体片段的新型C3对称手性结构。通过谐波光散射方法测定了其非线性光学性质，并探讨了新型发色团可能作为八极子的潜力。
• 신규한 싸이오펜 유도체, 그 제조방법 및 이를 포함하는 유기태양전지
  申请人：Industry-Academic Cooperation Foundation, Dankook University 단국대학교 산학협력단(220050166344) BRN ▼106-82-12299

  公开号：KR20150041434A

  公开（公告）日：2015-04-16

  작은 밴드갭을 갖는 싸이오펜 단위와 비닐렌 단위로 이루어진 전자주게 블록과 전자받게 블록을 공중합함으로써 태양광의 효과적인 흡수를 통한 고효율의 태양전지를 제조할 수 있는 신규한 싸이오펜 유도체, 그 제조방법 및 이를 포함하는 유기태양전지가 제공된다. 본 발명에 따르면, 작은 밴드갭을 가지는 신규한 싸이오펜 유도체를 통하여 태양광을 효과적으로 흡수할 수 있고, 용해도를 증가시킬 수 있으며, 성능이 향상된 유기태양전지를 제공할 수 있다.

  通过聚合含有小带隙的噻吩单元和苯乙烯单元的电子受体块和电子给体块，制备了一种新型的噻吩衍生物，可通过有效吸收太阳能实现高效率太阳能电池的制造。该发明提供了一种新型的噻吩衍生物，可有效吸收太阳能，增加溶解度，并提供性能更好的有机太阳能电池。
• Synthesis, structures, and optical and electrochemical characteristics of novel crown-containing polythiophene systems
  作者：E. V. Lukovskaya、A. A. Bobylyova、O. A. Fedorova、Yu. V. Fedorov、A. V. Anisimov、Y. Didane、H. Brisset、F. Fages

  DOI：10.1007/s11172-007-0146-5

  日期：2007.5

  The synthesis, structures, and optical and electrochemical characteristics of novel crown-containing styryl mono-and polythiophenes were described. The double bonds were constructed by the Horner-Wadsworth-Emmons method. The Suzuki and Stille cross-coupling reactions were used to create polythiophene chains. Optical measurements revealed intense absorption and fluorescence of crown-containing polythiophenes; the band positions and shapes in their absorption and emission spectra depend on the structure of the polythiophene. The electrochemical characteristics of the compounds obtained were measured.

  合成了新型含冠烷的单-和聚噻吩的结构、光学及电化学特性。通过霍纳－沃兹沃斯－埃蒙斯法构建了双键。采用铃木和斯蒂尔交叉耦合反应合成了聚噻吩链。光学测量显示含冠烷的聚噻吩具有强烈的吸收和荧光；其吸收和发射光谱中的波段位置和形状依赖于聚噻吩的结构。对所获得化合物的电化学特性进行了测量。
• A General Strategy to Design Highly Fluorogenic Far‐Red and Near‐Infrared Tetrazine Bioorthogonal Probes
  作者：Wuyu Mao、Jie Tang、Liqun Dai、Xinyu He、Jie Li、Larry Cai、Ping Liao、Ruotian Jiang、Jingwei Zhou、Haoxing Wu

  DOI：10.1002/anie.202011544

  日期：2021.2

  Highly fluorogenic tetrazine bioorthogonal probes emitting at near‐infrared wavelengths are in strong demand for biomedical imaging applications. Herein, we have developed a strategy for forming a palette of novel Huaxi‐Fluor probes in situ, whose fluorescence increases hundreds of times upon forming the bioorthogonal reaction product, pyridazine. The resulting probes show large Stokes shifts and high

  在生物医学成像应用中，强烈需求以近红外波长发射的高度荧光的四嗪生物正交探针。在这里，我们已经开发出一种在原位形成新型Huaxi-Fluor探针的调色板的策略，当形成生物正交反应产物哒嗪时，其荧光增加数百倍。所得探针显示出大的斯托克斯位移和高量子产率。通过操纵荧光团骨架中的共轭长度和推拉强度，可以将发射波长从556 nm微调到728 nm。具有高度光稳定性和生物相容性的探针适用于可视化活细胞中的细胞器，而无需清洗步骤，也适用于通过双光子激发将活体小动物中的肿瘤成像至500μm的深度。
• Solution processable star-shaped molecules with a triazine core and branching thienylenevinylenes for bulk heterojunction solar cells
  作者：Chien-Yi Huang、Wan-Hua Lee、Rong-Ho Lee

  DOI：10.1039/c4ra07139e

  日期：——

  Two new star-shaped A–π–D molecules with triazine as a core and an acceptor unit, thienylenevinylene as the π bridge, and tert-butyl-substituted triphenylamine (tTPA)- or carbazole (tCz) as the end group and donor units of TTVTPA and TTVCz were synthesized for their application as donor materials in solution processed bulk heterojunction organic solar cells (OSCs).

  两种新的星形A-π-D分子，以三嗪为核心和受体单元，噻吩亚乙烯为π桥，以叔丁基取代的三苯胺（tTPA）或碳酰胺（tCz）作为TTVTPA和TTVCz的终端基团和给体单元，用于它们在溶液处理的体异质结有机太阳能电池（OSCs）中的应用而合成。