Shielding Unit Engineering of NIR-II Molecular Fluorophores for Improved Fluorescence Performance and Renal Excretion Ability
Molecular fluorophores emitting in the second near-infrared (NIR-II) window with good renal excretion ability are favorable for in vivo bio-imaging and clinical applications. So far, renally excretable fluorophores are still less studied. Understanding the influences of molecular structure on optica...
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doaj-5fd8ae9c6e9843dea2032f8c2ac176512021-09-04T02:40:17ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462021-09-01910.3389/fchem.2021.739802739802Shielding Unit Engineering of NIR-II Molecular Fluorophores for Improved Fluorescence Performance and Renal Excretion AbilityChunchen Liu0Huilong Ma1Zhubin Hu2Rui Tian3Rui Ma4Yifan Xu5Xinyuan Wang6Xingfu Zhu7Panpan Yu8Shoujun Zhu9Haitao Sun10Yongye Liang11Department of Materials Science and Engineering, Shenzhen Key Laboratory of Printed Organic Electronics, Southern University of Science and Technology, Shenzhen, ChinaDepartment of Materials Science and Engineering, Shenzhen Key Laboratory of Printed Organic Electronics, Southern University of Science and Technology, Shenzhen, ChinaState Key Laboratory of Precision Spectroscopy, East China Normal University, Shanghai, ChinaState Key Laboratory of Molecular Vaccinology and Molecular Diagnostics and Center for Molecular Imaging and Translational Medicine School of Public Health, Xiamen University, Xiamen, ChinaDepartment of Materials Science and Engineering, Shenzhen Key Laboratory of Printed Organic Electronics, Southern University of Science and Technology, Shenzhen, ChinaDepartment of Materials Science and Engineering, Shenzhen Key Laboratory of Printed Organic Electronics, Southern University of Science and Technology, Shenzhen, ChinaDepartment of Materials Science and Engineering, Shenzhen Key Laboratory of Printed Organic Electronics, Southern University of Science and Technology, Shenzhen, ChinaDepartment of Materials Science and Engineering, Shenzhen Key Laboratory of Printed Organic Electronics, Southern University of Science and Technology, Shenzhen, ChinaDepartment of Materials Science and Engineering, Shenzhen Key Laboratory of Printed Organic Electronics, Southern University of Science and Technology, Shenzhen, ChinaState Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, ChinaState Key Laboratory of Precision Spectroscopy, East China Normal University, Shanghai, ChinaDepartment of Materials Science and Engineering, Shenzhen Key Laboratory of Printed Organic Electronics, Southern University of Science and Technology, Shenzhen, ChinaMolecular fluorophores emitting in the second near-infrared (NIR-II) window with good renal excretion ability are favorable for in vivo bio-imaging and clinical applications. So far, renally excretable fluorophores are still less studied. Understanding the influences of molecular structure on optical properties and renal excretion abilities are vital for fluorophore optimization. Herein, a series of shielding unit-donor-acceptor-donor-shielding unit (S-D-A-D-S) NIR-II molecular fluorophores are designed and synthesized with dialkoxy chains substituted benzene as the S unit. The anchoring positions of dialkoxy chains on benzene are tuned as meso-2,6, para-2,5, or ortho-3,4 to afford three fluorophores: BGM6P, BGP6P and BGO6P, respectively. Experimental and calculation results reveal that alkoxy side chains anchored closer to the conjugated backbone can provide better protection from water molecules and PEG chains, affording higher fluorescence quantum yield (QY) in aqueous solutions. Further, these side chains can enable good encapsulation of backbone, resulting in decreased binding with albumin and improved renal excretion. Thus, fluorophore BGM6P with meso-2,6-dialkoxy chains exhibits the highest quantum yield and fastest renal excretion. This work emphasizes the important roles of side chain patterns on optimizing NIR-II fluorophores with high brightness and renal excretion ability.https://www.frontiersin.org/articles/10.3389/fchem.2021.739802/fullNIR-II fluorophoresshielding unitS-D-A-D-S structurefluorescence performancerenal excretion |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Chunchen Liu Huilong Ma Zhubin Hu Rui Tian Rui Ma Yifan Xu Xinyuan Wang Xingfu Zhu Panpan Yu Shoujun Zhu Haitao Sun Yongye Liang |
spellingShingle |
Chunchen Liu Huilong Ma Zhubin Hu Rui Tian Rui Ma Yifan Xu Xinyuan Wang Xingfu Zhu Panpan Yu Shoujun Zhu Haitao Sun Yongye Liang Shielding Unit Engineering of NIR-II Molecular Fluorophores for Improved Fluorescence Performance and Renal Excretion Ability Frontiers in Chemistry NIR-II fluorophores shielding unit S-D-A-D-S structure fluorescence performance renal excretion |
author_facet |
Chunchen Liu Huilong Ma Zhubin Hu Rui Tian Rui Ma Yifan Xu Xinyuan Wang Xingfu Zhu Panpan Yu Shoujun Zhu Haitao Sun Yongye Liang |
author_sort |
Chunchen Liu |
title |
Shielding Unit Engineering of NIR-II Molecular Fluorophores for Improved Fluorescence Performance and Renal Excretion Ability |
title_short |
Shielding Unit Engineering of NIR-II Molecular Fluorophores for Improved Fluorescence Performance and Renal Excretion Ability |
title_full |
Shielding Unit Engineering of NIR-II Molecular Fluorophores for Improved Fluorescence Performance and Renal Excretion Ability |
title_fullStr |
Shielding Unit Engineering of NIR-II Molecular Fluorophores for Improved Fluorescence Performance and Renal Excretion Ability |
title_full_unstemmed |
Shielding Unit Engineering of NIR-II Molecular Fluorophores for Improved Fluorescence Performance and Renal Excretion Ability |
title_sort |
shielding unit engineering of nir-ii molecular fluorophores for improved fluorescence performance and renal excretion ability |
publisher |
Frontiers Media S.A. |
series |
Frontiers in Chemistry |
issn |
2296-2646 |
publishDate |
2021-09-01 |
description |
Molecular fluorophores emitting in the second near-infrared (NIR-II) window with good renal excretion ability are favorable for in vivo bio-imaging and clinical applications. So far, renally excretable fluorophores are still less studied. Understanding the influences of molecular structure on optical properties and renal excretion abilities are vital for fluorophore optimization. Herein, a series of shielding unit-donor-acceptor-donor-shielding unit (S-D-A-D-S) NIR-II molecular fluorophores are designed and synthesized with dialkoxy chains substituted benzene as the S unit. The anchoring positions of dialkoxy chains on benzene are tuned as meso-2,6, para-2,5, or ortho-3,4 to afford three fluorophores: BGM6P, BGP6P and BGO6P, respectively. Experimental and calculation results reveal that alkoxy side chains anchored closer to the conjugated backbone can provide better protection from water molecules and PEG chains, affording higher fluorescence quantum yield (QY) in aqueous solutions. Further, these side chains can enable good encapsulation of backbone, resulting in decreased binding with albumin and improved renal excretion. Thus, fluorophore BGM6P with meso-2,6-dialkoxy chains exhibits the highest quantum yield and fastest renal excretion. This work emphasizes the important roles of side chain patterns on optimizing NIR-II fluorophores with high brightness and renal excretion ability. |
topic |
NIR-II fluorophores shielding unit S-D-A-D-S structure fluorescence performance renal excretion |
url |
https://www.frontiersin.org/articles/10.3389/fchem.2021.739802/full |
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