1,2-bis[2-methyl-5-(1-naphthyl)-3-thienyl]perfluorocyclopentene | 854260-96-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2-bis[2-methyl-5-(1-naphthyl)-3-thienyl]perfluorocyclopentene
• 英文别名: 1,2-bis(2-methyl-5-naphthyl-3-thienyl)perfluorocyclopentene；1,2-Bis(2-methyl-5-(1-naphthyl)-3-thienyl)perfluorocyclopentene；3-[3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-naphthalen-1-ylthiophen-3-yl)cyclopenten-1-yl]-2-methyl-5-naphthalen-1-ylthiophene
• CAS: 854260-96-1
• 化学式: C₃₅H₂₂F₆S₂
• 分子量: 620.682
• InChiKey: XZAOSJJHNAOLDB-UHFFFAOYSA-N

物化性质

• 沸点：
  638.1±55.0 °C(predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  43
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2-bis[2-methyl-5-(1-naphthyl)-3-thienyl]perfluorocyclopentene 以 正己烷 为溶剂， 生成 1,2-dimethyl-8,8,9,9,10,10-hexafluoro-4,14-di(1-naphthyl)-3,15-dithiatetracyclo[10.3.0.0(2,6).0(7,11)]pentadeca-4,6(7),11(12),13-tetraene
  参考文献：
  名称：

  手性二芳基乙烯与八氟萘的共晶体中的绝对不对称光环化。

  摘要：

  当与八氟萘共结晶时，含有萘基的光致变色二芳基乙烯形成手性晶体，尽管两个分子都是非手性的，并且由于在晶体中的构象限制而经历了高度对映选择性的光环化。

  DOI：

  10.1039/b713694c
• 作为产物：
  描述：

  4-溴-5-甲基噻吩-2-硼酸 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 生成 1,2-bis[2-methyl-5-(1-naphthyl)-3-thienyl]perfluorocyclopentene
  参考文献：
  名称：

  Syntheses and optoelectronic properties of four photochromic dithienylethenes

  摘要：

  Four photochromic dithienylethene compounds, 1,2-bis(2-methyl-5-naphthalene-3-thienyl)perfluorocyclopentene 1a, 1,2-bis[2-methyl-5(p-fluorophenyl)-3-thienyl]perfluorocyclopentene 2a, 1,2-bis[2-methyl-5(p-ethoxyphenyl)-3-thienyl]perfluorocyclopentene 3a, and 1,2-bis[2-methyl-5(p-N,N-dimethylaminophenyl)-3-thienyl]perfluorocyclopentene 4a were synthesized, and their optoelectronic properties, such as photochromism in solution as well as in poly-methylmethacrylate (PMMA) amorphous films, fluorescences and electrochemical properties were investigated in detail. These dithienylethenes have shown good photochromic behavior both in solution and in PMMA amorphous film. All of them exhibited relatively strong fluorescence and gave a bathochromic shift upon increasing concentration in THF. The irreversible anodic oxidation of la, 2a and 4a was observed by performing cyclic voltammetry experiments. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.044

文献信息

• Functionalization of a Simple Dithienylethene via Palladium-Catalyzed Regioselective Direct Arylation
  作者：Hiroki Kamiya、Shuichi Yanagisawa、Satoru Hiroto、Kenichiro Itami、Hiroshi Shinokubo

  DOI：10.1021/ol2026069

  日期：2011.12.16

  The direct arylation on the thienyl groups of a diarylethene with various aryl iodides efficiently provided arylated dithienylethenes under palladium catalysis. Unsymmetrically substituted dithienylethenes were also synthesized by this protocol. This procedure allows a rapid access to a variety of aryl-substituted dithienylethenes from a single substrate of a simple dithienylethene.

  在钯催化下，二芳基乙烯的噻吩基与各种芳基碘化物的直接芳基化有效地提供了芳基化的二噻吩基乙烯。该协议还合成了不对称取代的二噻吩基乙烯。该方法允许从简单的二噻吩基乙烯的单个底物快速获得各种芳基取代的二噻吩基乙烯。
• Syntheses and optoelectronic properties of four photochromic dithienylethenes
  作者：Shouzhi Pu、Tianshe Yang、Jingkun Xu、Liang Shen、Guizhen Li、Qiang Xiao、Bing Chen

  DOI：10.1016/j.tet.2005.04.044

  日期：2005.7

  Four photochromic dithienylethene compounds, 1,2-bis(2-methyl-5-naphthalene-3-thienyl)perfluorocyclopentene 1a, 1,2-bis[2-methyl-5(p-fluorophenyl)-3-thienyl]perfluorocyclopentene 2a, 1,2-bis[2-methyl-5(p-ethoxyphenyl)-3-thienyl]perfluorocyclopentene 3a, and 1,2-bis[2-methyl-5(p-N,N-dimethylaminophenyl)-3-thienyl]perfluorocyclopentene 4a were synthesized, and their optoelectronic properties, such as photochromism in solution as well as in poly-methylmethacrylate (PMMA) amorphous films, fluorescences and electrochemical properties were investigated in detail. These dithienylethenes have shown good photochromic behavior both in solution and in PMMA amorphous film. All of them exhibited relatively strong fluorescence and gave a bathochromic shift upon increasing concentration in THF. The irreversible anodic oxidation of la, 2a and 4a was observed by performing cyclic voltammetry experiments. (c) 2005 Elsevier Ltd. All rights reserved.
• Absolute asymmetric photocyclization in chiral diarylethene co-crystals with octafluoronaphthalene
  作者：Masakazu Morimoto、Seiya Kobatake、Masahiro Irie

  DOI：10.1039/b713694c

  日期：——

  photochromic diarylethene containing naphthyl groups formed a chiral crystal when co-crystallized with octafluoronaphthalene, although both molecules are achiral, and underwent highly enantioselective photocyclization owing to the conformational confinement in the crystal.

  当与八氟萘共结晶时，含有萘基的光致变色二芳基乙烯形成手性晶体，尽管两个分子都是非手性的，并且由于在晶体中的构象限制而经历了高度对映选择性的光环化。