diethyl (2,2'-bithien-5-yl)methylphosphonate | 253344-94-4

• 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: diethyl (2,2'-bithien-5-yl)methylphosphonate
• 英文别名: diethyl (5-(thiophen-2-yl)thiophen-2-yl)methylphosphonate；2-(Diethoxyphosphorylmethyl)-5-thiophen-2-ylthiophene
• CAS: 253344-94-4
• 化学式: C₁₃H₁₇O₃PS₂
• 分子量: 316.382
• InChiKey: YMNXNWDCSPDPQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  92
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (2,2'-bithien-5-yl)methylphosphonate 在 正丁基锂 、 15-冠醚-5 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 N,N-diphenyl-4-[(E)-2-(5'-iodo-2,2'-bithien-5-yl)-1-ethenyl]aniline
  参考文献：
  名称：

  Donor−Acceptor-Substituted Phenylethenyl Bithiophenes:  Highly Efficient and Stable Nonlinear Optical Chromophores

  摘要：

  [GRAPHICS]For practical applications of poled electrooptic polymers, highly efficient and thermally stable nonlinear optical (NLO) chromophores are required. We describe here a concise synthesis and characterization of a series of donor-acceptor chromophores incorporating a bithiophene moiety in the conjugated bridge. They display a suitable thermal stability and significantly enhanced molecular nonlinearity as compared to their monothiophene analogues and are among the most efficient yet stable NLO chromophores prepared so far.

  DOI：

  10.1021/ol991118r
• 作为产物：
  描述：

  5-溴甲基-2-溴噻吩 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 33.0h， 生成 diethyl (2,2'-bithien-5-yl)methylphosphonate
  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

• Nonlinear optical compounds and related macrostructures
  申请人：University of Washington

  公开号：US07601849B1

  公开（公告）日：2009-10-13

  Nonlinear optically active compounds, macrostructures that include nonlinear optically active components, and devices including the macrostructures. The nonlinear optically active compounds include dendrimers having two or more nonlinear optically active components. In certain embodiments, the compounds and dendrimers are crosslinkable.

  非线性光学活性化合物，包括非线性光学活性组分的宏观结构，以及包括这些宏观结构的器件。非线性光学活性化合物包括具有两个或更多非线性光学活性组分的树状聚合物。在某些实施例中，这些化合物和树状聚合物是可交联的。
• Lewis Acid-Mediated Michaelis−Arbuzov Reaction at Room Temperature: A Facile Preparation of Arylmethyl/Heteroarylmethyl Phosphonates
  作者：Ganesan Gobi Rajeshwaran、Meganathan Nandakumar、Radhakrishnan Sureshbabu、Arasambattu K Mohanakrishnan

  DOI：10.1021/ol1029436

  日期：2011.3.18

  A facile preparation of arylmethyl and heteroarylmethyl phosphonate esters was achieved involving a Lewis acid mediated Michaelis-Arbuzov reaction at room temperature. Interaction of arylmethyl halides/alcohols with triethyl phosphite in the presence of Lewis acid at room temperature afforded phosphonate esters in good yields.
• A facile synthesis of thienylmethylphosphonates: direct conversion from thiophenes
  作者：Chuanguang Wang、Larry R Dalton

  DOI：10.1016/s0040-4039(99)02168-1

  日期：2000.1

  An efficient approach to thienylmethylphosphonates has been established through the combination of thienylcoppers with the commercially available diethyl iodomethylphosphonates in a one-pot process. (C) 2000 Elsevier Science Ltd. All rights reserved.
• NOVEL AMINO GROUP-CONTAINING HETEROCYCLIC DERIVATIVES AND SENSITIZING DYES FOR PHOTOELECTRIC CONVERSION CONTAINING THE HETEROCYCLIC DERIVATIVES
  申请人：Iida Katsumi

  公开号：US20090025781A1

  公开（公告）日：2009-01-29

  It is intended to provide novel amino group-containing heterocyclic derivatives, which have a broad absorption zone in the visible region and are suitable for sensitizing dyes for photoelectric conversion having a high photoelectric conversion efficiency, and photoelectric conversion materials, photoelectric conversion electrodes and photoelectric conversion cells using the same. Namely, a heterocyclic derivative represented by the following general formula (I) and containing an amino group at the terminus: wherein R 1 , R 2 , R 4 and R 5 independently represent each a hydrogen atom or a monovalent organic group optionally having one or more substituent; R 3 represents an anchor group capable of binding to an inorganic porous material showing semiconductor characteristics; X represents a divalent aromatic hydrocarbon group or a combination of two or more aromatic hydrocarbons being divalent or higher; Y represents a divalent aromatic heterocyclic group having a sulfur atom; Z represents a divalent aromatic heterocyclic group, a divalent aromatic hydrocarbon group, a divalent unsaturated hydrocarbon group or a combination thereof; and m is an integer of from 1 to 3.
• US8044219B2
  申请人：——

  公开号：US8044219B2

  公开（公告）日：2011-10-25