Li Guojuan, Fan Chunying, Cheng Guo, Wu Wanhua, Yang Cheng
Key Laboratory of Green Chemistry & Technology, College of Chemistry and Healthy Food Evaluation Research Center, Sichuan University, 29 Wangjiang Road, Chengdu, 610064, P. R. China.
Beilstein J Org Chem. 2019 Jul 18;15:1601-1611. doi: 10.3762/bjoc.15.164. eCollection 2019.
Planar chiral pillar[5]arene derivatives ( and ) bearing bulky fluorophores were obtained in high yield by click reaction. The photophysical properties of both compounds were investigated in detail. with two 9,10-diphenylanthracene (DPA) pigments grafted on the pillar[5]arene showed a high fluorescence quantum yield of 89.5%. This is comparable to the monomer , while with two perylene (Py) pigments grafted on the pillar[5]arene showed a significantly reduced quantum yield of 46.4% vs 78.2% for the monomer . The oxygen-through-annulus rotation of the phenolic units was inhibited for both compounds due to the bulky chromophore introduced, and the resolution of the enantiomers was achieved due to the bulky size of the fluorophores. The absolute configuration of the enantiomers was determined by circular dichroism (CD) spectra. The solvent-induced aggregation behavior was investigated with the enantiopure and . It was found that the CD signals were enhanced by aggregation. showed aggregation-induced emission enhancement, while showed aggregation-induced emission quenching, accompanied by excimer emission when aggregating in water and THF mixed solution.
通过点击反应以高产率获得了带有大体积荧光团的平面手性柱[5]芳烃衍生物（ 和 ）。详细研究了这两种化合物的光物理性质。在柱[5]芳烃上接枝两个9,10 - 二苯基蒽（DPA）颜料的 显示出89.5%的高荧光量子产率。这与单体相当，而在柱[5]芳烃上接枝两个苝（Py）颜料的 与单体78.2%相比，量子产率显著降低至46.4%。由于引入了大体积发色团，两种化合物中酚单元的氧通过环旋转均受到抑制，并且由于荧光团的大体积尺寸实现了对映体的拆分。通过圆二色性（CD）光谱确定了对映体的绝对构型。用对映体纯的 和 研究了溶剂诱导的聚集行为。发现聚集增强了CD信号。 显示出聚集诱导的发射增强，而 显示出聚集诱导的发射猝灭，在水和四氢呋喃混合溶液中聚集时伴有准分子发射。
