聚集诱导发光活性氟硼吡啶肼醛腙染料的合成、晶体结构及光学性质
收稿日期: 2024-03-22
修回日期: 2024-05-11
网络出版日期: 2024-06-13
基金资助
国家自然科学基金(22271002); 安徽省自然科学基金(2008085QB67); 安徽省自然科学基金(2308085J14); 安徽省高等学校科学研究项目(2023AH050149); 安徽省高等学校科学研究项目(KJ2021A0126); 安徽省教育厅高校优秀科研创新团队(2022AH010073)
Aggregation-Induced Emission (AIE) Active Fluoroboronated Pyridylhydrazinyl Aldehyde Hydrozone Dyes: Synthesis, Crystal Structure and Optical Properties
Received date: 2024-03-22
Revised date: 2024-05-11
Online published: 2024-06-13
Supported by
National Natural Science Foundation of China(22271002); Anhui Provincial Natural Science Foundation(2008085QB67); Anhui Provincial Natural Science Foundation(2308085J14); Scientific Research Project of Anhui Provincial Colleges and Universities(2023AH050149); Scientific Research Project of Anhui Provincial Colleges and Universities(KJ2021A0126); Excellent Scientific Research and Innovation Team in Natural Sciences of Anhui Provincial Department of Education(2022AH010073)
通过简单易得的氯代2-肼基吡啶和芳香醛衍生物缩合与氟硼配位, 一锅两步反应合成了系列新型的氟硼配位吡啶肼基醛腙染料, 将其命名为BOPAHs. 这些染料分子通过核磁共振、高分辨质谱和晶体结构进行了表征. 其主吸收在400~600 nm范围内, 发射波长在500~700 nm范围内. 随着溶剂极性的增加, 它们的吸收/发射峰逐渐红移, 同时斯托克斯位移增大, 表明这些分子具有明显的分子内电荷转移特性. 同时, 通过密度泛函理论计算进一步证实了这一特性. 此外, 这些BOPAHs在溶液中的荧光较弱, 但它们都表现出明显的聚集诱导发射特性, 可能是由于分子在聚集态下构象固定导致弱的分子间相互作用所致.
宫清宝 , 吕翔 , 于长江 , 李婉婉 , 赵全胜 , 焦莉娟 , 郝二红 . 聚集诱导发光活性氟硼吡啶肼醛腙染料的合成、晶体结构及光学性质[J]. 有机化学, 2024 , 44(8) : 2545 -2553 . DOI: 10.6023/cjoc202403032
A new family of fluoroboronated pyridylhydrazinyl aldehyde hydrozone fluorophores named BOPAHs were developed via a simple one-pot two-step reaction from chloro-2-hydrazinylpyridine and aromatic aldehyde derivatives. They were well characterized by NMR, HRMS, and X-ray crystal structures. They exhibit main absorption from 400 nm to 600 nm and emission bands from 500 nm to 700 nm. The absorption/emission bands redshift with increased polarity of solvents indicate a distinct intramolecular charge transfer characteristic, further confirmed by density functional theory (DFT) calculations. These BOPAHs display weak fluorescence in solutions, but they exhibit obvious aggregation-induced emission properties, possibly resulting from weak intermolecular interactions by fixing the molecular conformations in aggregate states.
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