面性不斉［2.2］パラシクロファンを基盤とする光学活性π共役系分子の合成

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タイトル別名
  • Synthesis of Optically Active π-Conjugated Molecules Based on Planar Chiral [2.2]Paracyclophane
  • メンセイ フセイ[2.2]パラシクロファン オ キバン ト スル コウガク カッセイpキョウヤクケイ ブンシ ノ ゴウセイ

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<p>We have focused on planar chirality of [2.2]paracyclophanes with substituent(s). In addition, we have developed their practical optical resolution methods by mainly diastereomer methods and synthetic routes to planar chiral [2.2]paracyclophane compounds. The obtained optically active disubstituted and tetrasubstituted [2.2]paracyclophanes have been utilized for chiral building blocks to produce a wide variety of optically active π-stacked molecules including polymers. The planar chiral [2.2]paracyclophane-based π-stacked molecules exhibited circularly polarized luminescence (CPL) with a large dissymmetry factor (glum value) derived from the optically active second-ordered structures, such as V-, X-, triangle-, one-handed double helical structures, in the excited state. It was the first example on the application of the planar chirality of [2.2]paracyclophane to the field of polymer chemistry as well as materials chemistry. π-Electron systems constructed by [2.2]paracyclophane emit photoluminescence (PL) depending on the conjugation length of the stacked π-electron system. When conjugation length of a stacked π-electron system is extended, the molecule exhibits monomeric PL rather than excimer-like PL despite the stacked structure in proximity. Even if the several tens of π-electron systems are stacked, PL profiles such as PL life time and quantum efficiency are identical. π-Conjugation lengths of monomeric π-electron systems in this article are sufficiently extended; thus, the [2.2]paracyclophane-based π-stacked molecules in this article emit brightly with good PL quantum efficiencies. Moreover, the luminescence is CPL with the large glum value in organic molecules. It is quite difficult to achieve CPL with high brightness, high PL efficiency, and large glum value by using other scaffolds; therefore, planar chiral [2.2]paracyclophane is the ideal scaffold to be an excellent CPL emitters.</p>

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