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Simultaneously boosting the conjugation, brightness and solubility of organic fluorophores by using AIEgens

Organic near-infrared (NIR) emitters hold great promise for biomedical applications. Yet, most organic NIR fluorophores face the limitations of short emission wavelengths, low brightness, unsatisfactory processability, and the aggregation-caused quenching effect. Therefore, development of effective...

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Autores principales: Qi, Ji, Duan, Xingchen, Cai, Yuanjing, Jia, Shaorui, Chen, Chao, Zhao, Zheng, Li, Ying, Peng, Hui-Qing, Kwok, Ryan T. K., Lam, Jacky W. Y., Ding, Dan, Tang, Ben Zhong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8163428/
https://www.ncbi.nlm.nih.gov/pubmed/34123103
http://dx.doi.org/10.1039/d0sc03423a
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author Qi, Ji
Duan, Xingchen
Cai, Yuanjing
Jia, Shaorui
Chen, Chao
Zhao, Zheng
Li, Ying
Peng, Hui-Qing
Kwok, Ryan T. K.
Lam, Jacky W. Y.
Ding, Dan
Tang, Ben Zhong
author_facet Qi, Ji
Duan, Xingchen
Cai, Yuanjing
Jia, Shaorui
Chen, Chao
Zhao, Zheng
Li, Ying
Peng, Hui-Qing
Kwok, Ryan T. K.
Lam, Jacky W. Y.
Ding, Dan
Tang, Ben Zhong
author_sort Qi, Ji
collection PubMed
description Organic near-infrared (NIR) emitters hold great promise for biomedical applications. Yet, most organic NIR fluorophores face the limitations of short emission wavelengths, low brightness, unsatisfactory processability, and the aggregation-caused quenching effect. Therefore, development of effective molecular design strategies to improve these important properties at the same time is a highly pursued topic, but very challenging. Herein, aggregation-induced emission luminogens (AIEgens) are employed as substituents to simultaneously extend the conjugation length, boost the fluorescence quantum yield, and increase the solubility of organic NIR fluorophores, being favourable for biological applications. A series of donor–acceptor type compounds with different substituent groups (i.e., hydrogen, phenyl, and tetraphenylethene (TPE)) are synthesized and investigated. Compared to the other two analogs, MTPE-TP3 with TPE substituents exhibits the reddest fluorescence, highest brightness, and best solubility. Both the conjugated structure and twisted conformation of TPE groups endow the resulting compounds with improved fluorescence properties and processability for biomedical applications. The in vitro and in vivo applications reveal that the NIR nanoparticles function as a potent probe for tumour imaging. This study would provide new insights into the development of efficient building blocks for improving the performance of organic NIR emitters.
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spelling pubmed-81634282021-06-11 Simultaneously boosting the conjugation, brightness and solubility of organic fluorophores by using AIEgens Qi, Ji Duan, Xingchen Cai, Yuanjing Jia, Shaorui Chen, Chao Zhao, Zheng Li, Ying Peng, Hui-Qing Kwok, Ryan T. K. Lam, Jacky W. Y. Ding, Dan Tang, Ben Zhong Chem Sci Chemistry Organic near-infrared (NIR) emitters hold great promise for biomedical applications. Yet, most organic NIR fluorophores face the limitations of short emission wavelengths, low brightness, unsatisfactory processability, and the aggregation-caused quenching effect. Therefore, development of effective molecular design strategies to improve these important properties at the same time is a highly pursued topic, but very challenging. Herein, aggregation-induced emission luminogens (AIEgens) are employed as substituents to simultaneously extend the conjugation length, boost the fluorescence quantum yield, and increase the solubility of organic NIR fluorophores, being favourable for biological applications. A series of donor–acceptor type compounds with different substituent groups (i.e., hydrogen, phenyl, and tetraphenylethene (TPE)) are synthesized and investigated. Compared to the other two analogs, MTPE-TP3 with TPE substituents exhibits the reddest fluorescence, highest brightness, and best solubility. Both the conjugated structure and twisted conformation of TPE groups endow the resulting compounds with improved fluorescence properties and processability for biomedical applications. The in vitro and in vivo applications reveal that the NIR nanoparticles function as a potent probe for tumour imaging. This study would provide new insights into the development of efficient building blocks for improving the performance of organic NIR emitters. The Royal Society of Chemistry 2020-07-27 /pmc/articles/PMC8163428/ /pubmed/34123103 http://dx.doi.org/10.1039/d0sc03423a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Qi, Ji
Duan, Xingchen
Cai, Yuanjing
Jia, Shaorui
Chen, Chao
Zhao, Zheng
Li, Ying
Peng, Hui-Qing
Kwok, Ryan T. K.
Lam, Jacky W. Y.
Ding, Dan
Tang, Ben Zhong
Simultaneously boosting the conjugation, brightness and solubility of organic fluorophores by using AIEgens
title Simultaneously boosting the conjugation, brightness and solubility of organic fluorophores by using AIEgens
title_full Simultaneously boosting the conjugation, brightness and solubility of organic fluorophores by using AIEgens
title_fullStr Simultaneously boosting the conjugation, brightness and solubility of organic fluorophores by using AIEgens
title_full_unstemmed Simultaneously boosting the conjugation, brightness and solubility of organic fluorophores by using AIEgens
title_short Simultaneously boosting the conjugation, brightness and solubility of organic fluorophores by using AIEgens
title_sort simultaneously boosting the conjugation, brightness and solubility of organic fluorophores by using aiegens
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8163428/
https://www.ncbi.nlm.nih.gov/pubmed/34123103
http://dx.doi.org/10.1039/d0sc03423a
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