8,8'-(thiophene-2,5-diyldiethyne-2,1-diyl)bis[3,3-diphenyl-3H-naphtho[2,1-b]pyran] | 316127-66-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 8,8'-(thiophene-2,5-diyldiethyne-2,1-diyl)bis[3,3-diphenyl-3H-naphtho[2,1-b]pyran]
• 英文别名: 2,5-bis[(3,3diphenyl-[3H]-naphtho[2,1-b]pyran-8-yl)ethynyl]thiophene；8-[2-[5-[2-(3,3-Diphenylbenzo[f]chromen-8-yl)ethynyl]thiophen-2-yl]ethynyl]-3,3-diphenylbenzo[f]chromene
• CAS: 316127-66-9
• 化学式: C₅₈H₃₆O₂S
• 分子量: 796.989
• InChiKey: YCQKVZIUXKFEKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.2
• 重原子数：
  61
• 可旋转键数：
  8
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8,8'-(thiophene-2,5-diyldiethyne-2,1-diyl)bis[3,3-diphenyl-3H-naphtho[2,1-b]pyran] 以 氘代甲苯 为溶剂， 反应 20.0h， 生成 6-[5-(3,3-Diphenyl-3H-benzo[f]chromen-8-ylethynyl)-thiophen-2-ylethynyl]-1-[3,3-diphenyl-prop-2-en-(E)-ylidene]-1H-naphthalen-2-one 、 6-[5-(3,3-Diphenyl-3H-benzo[f]chromen-8-ylethynyl)-thiophen-2-ylethynyl]-1-[3,3-diphenyl-prop-2-en-(Z)-ylidene]-1H-naphthalen-2-one 、 、
  参考文献：
  名称：

  Comprehensive Photokinetic and NMR Study of a Biphotochromic Supermolecule Involving Two Naphthopyrans Linked to a Central Thiophene Unit Through Acetylenic Bonds¶

  摘要：

  A photophysical and photochemical study of a biphotochromic compound where two naphthopyran units are linked by an acetylene-thiophene-acetylene bridge has been carried out in toluene. Both fluorescence and intersystem crossing to the triplet manifold were found to compete with the photo-coloration process. Two photoproducts (transoid-trans and transoid-cis stereoisomers), absorbing at similar to480 nm and corresponding to the opening of a single photochromic unit, were detected by spectrophotometric analysis after short irradiation time in diluted solution and identified by H-1-nuclear magnetic resonance (NMR) spectroscopy. After prolonged irradiation at 228 K of highly concentrated solutions (up to 3 x 10(-3) mol dm(-3)), two additional isomers, absorbing at similar to550 nm, were formed. Their NMR spectra indicate the opening of both photochromic units. An interesting effect of selective vibronic excitation was found, showing that the photoreaction is favored at excited vibronic levels to the detriment of the radiative relaxation.

  DOI：

  10.1562/0031-8655(2003)078<0558:cpanso>2.0.co;2
• 作为产物：
  描述：

  6-溴-2-萘酚 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 、 对甲苯磺酸 sodium hydroxide 、 copper(l) iodide 、 苄基三乙基氯化铵 、 二乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 88.0h， 生成 8,8'-(thiophene-2,5-diyldiethyne-2,1-diyl)bis[3,3-diphenyl-3H-naphtho[2,1-b]pyran]
  参考文献：
  名称：

  光调制材料。通过乙炔键连接噻吩单元的光致变色3H-萘并[2,1-b]吡喃的合成及性能

  摘要：

  描述了通过炔键连接到单-、二-或三噻吩的 3H-萘并[2,1-b]吡喃的合成（方案 2 和 3）。合成方法涉及连续的 Sonogashira 偶联反应。在连续辐照下研究了这些新型材料在溶液中的光致变色特性。

  DOI：

  10.1002/1522-2675(20001108)83:11<3043::aid-hlca3043>3.0.co;2-z

文献信息

• Synthesis and Photochromic Properties of Thiophene Linked [2<i>H</i>]-Chromenes
  作者：M. Frigoli、C. Moustrou、A. Samat、R. Guglielmetti、R. Dubest、J. Aubard

  DOI：10.1080/10587250008023827

  日期：2000.6.1

  Successive coupling reactions (catalysed by Cu(I)/Pd(II) systems) between 8-bromo-3,3-diphenyl-[3H]naphtho[2,1-b]pyran, 2-methylbut-3-yn-2-ol and appropriate thiophene- or bithiophene halides afforded mono- or bichromophoric chromenes bearing a thienylethynyl or a bithienyrethynyl group. Spectrokinetic study using flash photolysis conditions showed interesting photochromic properties regarding, especially, the " colorability " of the new compounds.
• US6281366B1
  申请人：——

  公开号：US6281366B1

  公开（公告）日：2001-08-28
• Photomodulable Materials. Synthesis and Properties of Photochromic 3H-Naphtho[2,1-b]pyrans Linked to Thiophene Unitsvia an Acetylenic Junction
  作者：Michel Frigoli、Corinne Moustrou、André Samat、Robert Guglielmetti

  DOI：10.1002/1522-2675(20001108)83:11<3043::aid-hlca3043>3.0.co;2-z

  日期：2000.11.8

  The synthesis of 3H-naphtho[2,1-b]pyrans linked to mono-, di-, or terthiophene via an acetylenic junction is described (Schemes 2 and 3). The synthetic approaches involve successive Sonogashira coupling reactions. The photochromic properties in solution of these novel materials were investigated under continuous irradiation.

  描述了通过炔键连接到单-、二-或三噻吩的 3H-萘并[2,1-b]吡喃的合成（方案 2 和 3）。合成方法涉及连续的 Sonogashira 偶联反应。在连续辐照下研究了这些新型材料在溶液中的光致变色特性。
• Comprehensive Photokinetic and NMR Study of a Biphotochromic Supermolecule Involving Two Naphthopyrans Linked to a Central Thiophene Unit Through Acetylenic Bonds¶
  作者：Fausto Ortica、Corinne Moustrou、Jérôme Berthet、Gianna Favaro、André Samat、Robert Guglielmetti、Gaston Vermeersch、Ugo Mazzucato

  DOI：10.1562/0031-8655(2003)078<0558:cpanso>2.0.co;2

  日期：——

  A photophysical and photochemical study of a biphotochromic compound where two naphthopyran units are linked by an acetylene-thiophene-acetylene bridge has been carried out in toluene. Both fluorescence and intersystem crossing to the triplet manifold were found to compete with the photo-coloration process. Two photoproducts (transoid-trans and transoid-cis stereoisomers), absorbing at similar to480 nm and corresponding to the opening of a single photochromic unit, were detected by spectrophotometric analysis after short irradiation time in diluted solution and identified by H-1-nuclear magnetic resonance (NMR) spectroscopy. After prolonged irradiation at 228 K of highly concentrated solutions (up to 3 x 10(-3) mol dm(-3)), two additional isomers, absorbing at similar to550 nm, were formed. Their NMR spectra indicate the opening of both photochromic units. An interesting effect of selective vibronic excitation was found, showing that the photoreaction is favored at excited vibronic levels to the detriment of the radiative relaxation.