2,5-bis(diphenylhydroxymethyl)thiophene | 136970-35-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-bis(diphenylhydroxymethyl)thiophene
• CAS: 136970-35-9
• 化学式: C₃₀H₂₄O₂S
• 分子量: 448.585
• InChiKey: ZOJZGYUUVCLEMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,5-bis(diphenylhydroxymethyl)thiophene 在 trimethylsilyl perchlorate 、 锌 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 26.5h， 生成 2,5-二(二苯基亚甲基)-2,5-二氢噻吩
  参考文献：
  名称：

  Preparation, Structure, and Redox Behavior of Bis(diarylmethylene)dihydrothiophene and Its π-Extended Analogues

  摘要：

  The preparation, X-ray structure, and optoelectronic properties of bis(diarylmethylene)dihydrothiophene 1 and its p-extended analogues 2 are described. The development of a simple, short-step synthetic route allowed us to prepare derivatives with different aryl units. X-ray crystallographic analysis of 1b and 2b revealed their quinoidal structures, which exhibit strong electronic absorption in the visible region. Cyclic voltammetry measurements revealed their strong electron-donating properties. 1b showed two-step electrochromic behavior between the corresponding radical cation and dication.

  DOI：

  10.1021/acs.joc.5b00021
• 作为产物：
  描述：

  二苯甲酮 、 2,5-dilithiothiophene 以 四氢呋喃 为溶剂， 生成 2,5-bis(diphenylhydroxymethyl)thiophene
  参考文献：
  名称：

  2,5-双（二芳基亚甲基）-2,5-二氢噻吩及其呋喃，硒烯和N-甲基吡咯类似物的制备

  摘要：

  一系列的2,5-双（二芳基亚甲基）-2,5-二氢噻吩及其呋喃，硒醚和N-甲基吡咯类似物可分三步合成，从2,5-二锂化的五元杂芳族化合物和2当量的二芳基开始酮或2,5-二氮酰基五元杂芳族化合物和2当量的芳基锂。

  DOI：

  10.1016/s0040-4039(00)92158-0

文献信息

• Synthesis of calix[n]furano[n]pyrroles and calix[n]thieno[n]pyrroles (n=2,3,4) by ‘3+1’ approach
  作者：Yong-Sung Jang、Han-Je Kim、Phil-Ho Lee、Chang-Hee Lee

  DOI：10.1016/s0040-4039(00)00294-x

  日期：2000.4

  Condensation of 5,5,10,10-tetramethyl-16-oxa-tripyrromethane and 2,5-bis[(alpha-hydroxy-alpha,alpha-dimethyl)methyl]furan or 2,5-bis[(alpha-hydroxy-alpha,alpha-dimethyl)methyl]thiophene resulted in cyclic, alternating oligomers of furan(thiophene) and pyrrole. The product distribution is independent of the reaction conditions, the presence of inorganic additives and temperature. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Calix[2]thia[4]phyrin: An Expanded Calixphyrin with Aggregation-Induced Enhanced Emission and Anion Receptor Properties
  作者：Ganesan Karthik、Pallavee Vitti Krushna、A. Srinivasan、Tavarekere K. Chandrashekar

  DOI：10.1021/jo401232a

  日期：2013.9.6

  The synthesis of calix[2]thia[4]phyrin 3, a core-modified expanded calixphyrin, by an efficient synthetic route is reported. 3 exhibits an aggregation-induced enhanced emission (AIEE) phenomenon upon addition of increasing amounts of water. This is attributed to the restricted intramolecular rotation of the meso-aryl rings present on the sp(3) bridging carbons. SEM studies revealed the formation of aggregation in an acetonitrile/water mixture with an average diameter of the aggregate in the range 0.38-2.08 mu m. The The photoluminescence quantum yield of 3 in 9:1 water/acetonitrile is 5-fold higher than the quantum yield in acetonitrile alone. Single-crystal X-ray analysis of 3 revealed a chairlike conformation stabilized by N-H center dot center dot center dot N and C-H center dot center dot center dot pi intramolecular hydrogen-bonding interactions. Fluorine atoms on the meso-pentafluorophenyl groups are involved in C-H center dot center dot center dot F intermolecular hydrogen-bonding interactions to generate a two-dimensional supramolecular assembly in the solid state. In the diprotonated state, 3 has affinity for anions and forms 1:1 complexes with SO42-, NO3-, Cl-, and ClO4- in solution. The tetrahedral anions bind more strongly than the other anions. Single-crystal X-ray structure studies of the ClO4- anion complex with 3 revealed the formation of both 1:1 and 1:2 complexes in the solid state, with the host and the guest being held together by N-H center dot center dot center dot O hydrogen-bonding interactions.