Rational Design of Push–Pull Fluorene Dyes: Synthesis and Structure–Photophysics Relationship,Chemistry - A European Journal

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Rational Design of Push–Pull Fluorene Dyes: Synthesis and Structure–Photophysics Relationship
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2016-06-15 , DOI: 10.1002/chem.201600581
Janah Shaya ₁ , Fabien Fontaine-Vive ₁ , Benoît Y. Michel ₁ , Alain Burger ₁

Affiliation

Our work surveyed experimental and theoretical investigations to construct highly emissive D–π–A (D=donor, A=acceptor) fluorenes. The synthetic routes were optimised to be concise and gram‐scalable. The molecular design was first rationalised by varying the electron‐withdrawing group from an aldehyde, ketotriazole or succinyl to methylenemalonitrile or benzothiadiazole. The electron‐donating group was next varied from aliphatic or aromatic amines to saturated cyclic amines ranging from aziridine to azepane. Spectroscopic studies correlated with TD‐DFT calculations provided the optimised structures. The selected push–pull dyes exhibited visible absorptions, significant brightness, important solvatofluorochromism, mega‐Stokes shifts (>250 nm) and dramatic shifts in emission to the near‐infrared. The current library includes the comprehensive characterization of 16 prospective dyes for fluorescence applications. Among them, several fluorene derivatives bearing different conjugation anchors were tested for coupling and demonstrated to preserve the photophysical responses once further bound.

中文翻译：

推挽式芴染料的合理设计：合成与结构-光物理关系

我们的工作通过实验和理论研究来构建高发射D–π–A（D =供体，A =受体）芴。优化了合成路线，使其简洁易行。首先通过将吸电子基团从醛，酮三唑或琥珀酰基改为亚甲基丙二腈或苯并噻二唑来合理化分子设计。接下来，给电子基团从脂肪族或芳香族胺到饱和环胺（从氮丙啶到氮杂环庚烷）不等。与TD-DFT计算相关的光谱研究提供了优化的结构。选定的推挽式染料表现出可见吸收，显着的亮度，重要的溶剂化荧光色，兆斯托克斯位移（> 250 nm）和向近红外光的发射急剧变化。当前的资料库包括16种用于荧光应用的前瞻性染料的全面表征。其中，

更新日期：2016-06-15

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