Basket-shaped quinacridone cyclophanes: synthesis, solid-state structures, and properties

Basket-shaped quinacridone cyclophanes: synthesis, solid-state structures, and properties
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DOI:
10.1039/c0nj00028k
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发表时间:
2010-10
影响因子:
3.3
通讯作者:
Dingyi Yu;Tai Peng;Hongyu Zhang;Hai Bi;Jingying Zhang;Yue Wang
Dingyi Yu;Tai Peng;Hongyu Zhang;Hai Bi;Jingying Zhang;Yue Wang
中科院分区:
化学3区
文献类型:
--
作者:
Dingyi Yu;Tai Peng;Hongyu Zhang;Hai Bi;Jingying Zhang;Yue Wang

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一系列篮状喹吖啶酮 (QA) 环芳烷 1-6 已被合成和表征。 5 的单晶 X 射线分析显示 QA 核心之间没有无限的 π-π 聚集,反映了桥连系链的显着孤立效应。光物理性质已被仔细研究。与非桥连的 QA 类似物 7 相比,所有环烷在浓溶液中都显示出更高的量子产率。1 作为绿色掺杂剂在 EL 器件中的进一步应用显示出电流效率分别为 11.2 和 7.2 cd A−1,掺杂浓度分别为 0.5 和 3 wt%。 QA 环烷在浓溶液和高掺杂浓度的 EL 器件中均保持高发光产率,验证了篮状功能化是抑制 QA 染料在凝聚相中荧光猝灭的理想策略。
A series of basket-shaped quinacridone (QA) cyclophanes 1–6 has been synthesized and characterized. Single-crystal X-ray analysis of 5 shows no infinite π–π aggregation between QA cores, reflecting a significant isolated effect of the bridging tethers. Photophysical properties have been carefully investigated. All cyclophanes show much higher quantum yields in concentrated solutions compared to the non-bridged QA analogue 7. Further application of 1 as a green dopant in EL devices exhibits current efficiencies of 11.2 and 7.2 cd A−1 with doping concentrations of 0.5 and 3 wt%, respectively. QA cyclophanes maintain a high luminescent yield in both concentrated solution and high doping concentration EL devices, verifying that the basket-shaped functionalization is an ideal strategy for depressing fluorescence quenching of QA dyes in the condensed phase.