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首页> 外文期刊>Dalton transactions: An international journal of inorganic chemistry >Dipyrrolylquinoxaline difluoroborates with intense red solid-state fluorescence
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Dipyrrolylquinoxaline difluoroborates with intense red solid-state fluorescence

机译：双吡咯基喹喔啉二氟硼酸盐具有强烈的红色固态荧光

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摘要

A set of organic fluorescent dyes of dipyrrolylquinoxalines (PQs 4-6) and their BF2 complexes (BPQs 1-3) were synthesized from commercial reagents, and were characterized by their X-ray structural analysis, and optical and electrochemical properties. BPQs 1-3 showed intense broad absorption in the visible region in the solution-state. In comparison with that of PQs 4-6, there is an over 110 nm red-shift of the absorption maximum in the BPQs 1-3 (up to 583 nm). Interestingly, dyes 1-6 all exhibit red solid-state fluorescence with moderate to high fluorescence quantum yields except for PQ 4 which showed bright yellow solid-state fluorescence. X-ray structures of BPQs 2-3 showed the planar structure of quinoxaline with one pyrrole unit via the BF2 chelation and the almost perpendicular orientation of the uncoordinated pyrrole to the NBN core plane (the dihedral angle of 70-73 degrees). The extended pi-conjugation was in good agreement with the observed red-shift of the spectra. These dyes formed well-ordered intermolecular packing structures via the intermolecular hydrogen bonding between the N atoms of quinoxaline moieties and the NH units of adjacent pyrroles. The lack of pi-pi stacking in their crystal packing structures may explain the interestingly intense solid-state fluorescence of these dyes.
机译：用商业试剂合成了一组二吡咯基喹喔啉类有机荧光染料（PQ 4-6）及其BF2配合物（BPQ 1-3），并通过X射线结构分析，光学和电化学性能对其进行了表征。 BPQs 1-3在溶液状态的可见光区域显示出强烈的广泛吸收。与PQ 4-6相比，BPQ 1-3（最大583 nm）的吸收最大值有超过110 nm的红移。有趣的是，除了PQ 4表现出亮黄色的固态荧光外，染料1-6均显示红色的固态荧光，具有中等至高的荧光量子产率。 BPQs 2-3的X射线结构通过BF2螯合显示了带有一个吡咯单元的喹喔啉的平面结构，未配位的吡咯几乎垂直于NBN核心平面取向（二面角为70-73度）。扩展的π共轭与观察到的光谱红移很好地吻合。这些染料通过喹喔啉基团的N原子与相邻吡咯的NH单元之间的分子间氢键形成有序的分子间堆积结构。它们的晶体堆积结构中缺少pi-pi堆积可能解释了这些染料有趣的强烈固态荧光。

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