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Janus 型 AIE 荧光团：π-扩展香豆素支载三环化合物的合成与性质。

Janus-Type AIE Fluorophores: Synthesis and Properties of π-Extended Coumarin-Bearing Triskelions.

机构信息

Department of Chemistry, Graduate School of Science, Kitasato University, Kanagawa 252-0373, Japan.

Department of Applied Chemistry, Faculty of Engineering, Chiba Institute of Technology, Chiba 275-0016, Japan.

出版信息

Molecules. 2022 Nov 2;27(21):7450. doi: 10.3390/molecules27217450.

DOI:10.3390/molecules27217450
PMID:36364275
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9656437/
Abstract

Janus-type triskelion-shaped fluorophores comprising coumarins bearing various electron-donating substituents (, , , and ) were successfully synthesized via an intramolecular Ullmann coupling. Density functional theory (DFT) calculations indicated that all the compounds presented two different molecular surfaces, similar to Janus-type molecules. The absorption and fluorescence spectra of asymmetrical derivatives , , , and exhibited a bathochromic shift due to their narrow highest occupied molecular orbital (HOMO) -lowest unoccupied molecular orbital (LUMO) gap. Natural transition orbital (NTO) analysis indicated that the excited state orbital overlaps differ among the symmetrical and asymmetrical dyes. These triskelion-shaped fluorophores were found to form molecular nanoaggregates in THF/HO mixtures and demonstrated aggregation-induced emission (AIE) enhancement characteristics as a result of restricting their molecular inversion. These results indicate that Janus-type AIE fluorophores are potentially applicable as solid-state fluorescent chiral materials, which can be optimized by controlling their molecular rearrangement in the solid state.

摘要

通过分子内 Ullmann 偶联反应，成功合成了含有各种供电子取代基（，，，和）的香豆素的 Janus 型三足形荧光团。密度泛函理论（DFT）计算表明，所有化合物都呈现出两种不同的分子表面，类似于 Janus 型分子。不对称衍生物，，，和的吸收和荧光光谱由于其较窄的最高占据分子轨道（HOMO）-最低未占据分子轨道（LUMO）能隙而发生红移。自然跃迁轨道（NTO）分析表明，对称和不对称染料的激发态轨道重叠不同。这些三足形荧光团在 THF/HO 混合物中形成分子纳米聚集体，并表现出聚集诱导发射（AIE）增强特性，这是由于限制了它们的分子反转。这些结果表明，Janus 型 AIE 荧光团有望用作固态荧光手性材料，通过控制其在固态中的分子重排来优化其性能。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/b61ce0c33ab8/molecules-27-07450-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/4076ad258179/molecules-27-07450-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/6ebfe6b3ee84/molecules-27-07450-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/241ee2d843d4/molecules-27-07450-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/9bf629c21559/molecules-27-07450-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/1254b87669ce/molecules-27-07450-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/5821844449d4/molecules-27-07450-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/157564fcca5a/molecules-27-07450-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/f8844e1a4f2b/molecules-27-07450-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/4853ca451f02/molecules-27-07450-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/b61ce0c33ab8/molecules-27-07450-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/4076ad258179/molecules-27-07450-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/6ebfe6b3ee84/molecules-27-07450-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/241ee2d843d4/molecules-27-07450-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/9bf629c21559/molecules-27-07450-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/1254b87669ce/molecules-27-07450-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/5821844449d4/molecules-27-07450-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/157564fcca5a/molecules-27-07450-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/f8844e1a4f2b/molecules-27-07450-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/4853ca451f02/molecules-27-07450-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48d7/9656437/b61ce0c33ab8/molecules-27-07450-g008.jpg

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本文引用的文献

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