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Coronenes with push–pull geometries from macrocycle-forming Perkin condensations
Chemical Communications ( IF 4.9 ) Pub Date : 2024-03-27 , DOI: 10.1039/d4cc00935e
Luc Soliman 1 , Elsa Ramassamy 1 , Katia Dujarric 1 , Guillaume Naulet 1 , Pierre Dechambenoit 1 , Harald Bock 1 , Fabien Durola 1
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Although the Perkin reaction has been successful in producing ester-substituted conjugated macrocycles with four or six building blocks, macrocycles composed of only two elements remained elusive until now. Through the development of a building block derived from phenanthrene with two glyoxylic acid substituents in a pincer-like arrangement, formation of a two-block macrocycle was induced when paired with a complementary phenylenediacetic acid unit. The addition of ether functions to the phenanthrene building block not only improved the yields, but led to macrocycles with push–pull geometries. Photocyclisation of the resulting cyclophanes efficiently yield tetra- and hexasubstituted coronenes.

中文翻译:

来自形成大环的珀金缩合的具有推拉几何形状的晕苯

尽管珀金反应已经成功地生产了具有四个或六个结构单元的酯取代的共轭大环化合物,但仅由两种元素组成的大环化合物迄今为止仍然难以捉摸。通过开发源自菲的结构单元,该结构单元具有钳状排列的两个乙醛酸取代基,当与互补的苯二乙酸单元配对时,诱导形成双嵌段大环。在菲结构单元中添加醚官能团不仅提高了产率,而且产生了具有推拉几何形状的大环化合物。所得环烷的光环化有效地产生四取代和六取代晕苯。
更新日期:2024-03-27
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