Rhodium-mediated enantioselective synthesis of a benzopicene-based phospha[9]helicene: the structure–property relationship of triphenylene- and benzopicene-based carbo- and phosphahelicenes†,Materials Chemistry Frontiers

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Rhodium-mediated enantioselective synthesis of a benzopicene-based phospha[9]helicene: the structure–property relationship of triphenylene- and benzopicene-based carbo- and phosphahelicenes†
Materials Chemistry Frontiers ( IF 6.0 ) Pub Date : 2018-01-15 00:00:00 , DOI: 10.1039/c7qm00581d
Shuhei Nishigaki _{1,

2,

3,

4,

5} , Koichi Murayama _{1,

2,

3,

4,

5} , Yu Shibata _{1,

2,

3,

4,

5} , Ken Tanaka _{1,

2,

3,

4,

5}

Affiliation

The enantioselective synthesis of a phospha[9]helicene with a bibenzopicene skeleton has been achieved via the rhodium-mediated intermolecular [2+2+2] cycloaddition of a binaphthyl-linked tetrayne with a phosphorus-linked diyne. The photophysical and chiroptical properties of the thus obtained phospha[9]helicene were compared with our previously synthesized benzopicene-based carbo[9]helicene and triphenylene-based carbo- and phospha[7]helicenes. Significantly red shifted absorption and emission maxima were observed in the benzopicene-based phospha[9]helicene as a result of extended π-conjugation, but its fluorescence quantum yield and circularly polarized luminescence activity (g_lum) were lower than those of the other three helicenes.

中文翻译：

铑介导的基于苯并吡啶的基于膦的对映体选择性合成[9] ic烯：基于三亚苯基和苯并吡啶的基于碳和磷杂环烯的结构与性质的关系†

通过联萘连接的四炔与磷连接的二炔的铑介导的[2 + 2 + 2]分子间[2 + 2 + 2]环加成反应，实现了具有联苯并吡啶骨架的磷[9]螺旋烯的对映选择性合成。将由此获得的磷[9]螺旋烯的光物理和手性性质与我们先前合成的基于苯并吡啶的碳[9]螺旋烯和三亚苯基的碳和磷[7]螺旋烯进行了比较。由于扩展的π共轭作用，在苯并picene-based phospha [9] helicene中观察到最大的红移吸收和发射最大值，但其荧光量子产率和圆偏振发光活性（g _lum）低于其他三个螺旋星。

更新日期：2018-01-15

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