Organic Nanocrystals Based on a Solid-emission-tunable AIEgen for Cell Imaging

doi:10.1007/s40242-020-0346-1

高等学校化学研究 ›› 2021, Vol. 37 ›› Issue (1): 129-136.doi: 10.1007/s40242-020-0346-1

Organic Nanocrystals Based on a Solid-emission-tunable AIEgen for Cell Imaging

YANG Liming¹, GUO Lixin¹, YU Hao¹, WANG Guan¹, SUN Jiangman¹, ZHANG Pengfei², GU Xinggui¹, TANG Ben Zhong³

1. Beijing Advanced Innovation Center for Soft Matter Science and Engineering, College of Materials Science and Engineering, State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing 100029, P. R. China;
2. Guangdong Key Laboratory of Nanomedicine, Shenzhen Engineering Laboratory of Nanomedicine and Nanoformulations, CAS Key Laboratory of Health Informatics, Institute of Biomedicine and Biotechnology, Shenzhen Institutes of Advanced Technology, Chinese Academy of Sciences, Shenzhen 518055, P. R. China;
3. Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, Institute for Advanced Study, The Hong Kong University of Science and Technology, Hong Kong, P. R. China

收稿日期:2020-10-28 修回日期:2020-11-23 出版日期:2021-02-01 发布日期:2020-11-30
通讯作者: ZHANG Pengfei, GU Xinggui, TANG Ben Zhong E-mail:pf.zhang@siat.ac.cn;guxinggui@mail.buct.edu.cn;tangbenz@ust.hk
基金资助:
This work was partially supported by the National Natural Science Foundation of China(Nos.21702016, 21905015 and 52003023), and the Fund of the Beijing National Laboratory for Molecular Sciences, China(No.BNLMS201813). B. Z. Tang acknowledges the financial support from the National Natural Science Foundation of China(No.21788102), the Research Grants Council of Hong Kong(Nos. N_HKUT609/19, 16305518, and C6009-17G), and the Innovation and Technology Commission(No.ITC-CNERC14SC01).

Organic Nanocrystals Based on a Solid-emission-tunable AIEgen for Cell Imaging

YANG Liming¹, GUO Lixin¹, YU Hao¹, WANG Guan¹, SUN Jiangman¹, ZHANG Pengfei², GU Xinggui¹, TANG Ben Zhong³

1. Beijing Advanced Innovation Center for Soft Matter Science and Engineering, College of Materials Science and Engineering, State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing 100029, P. R. China;
2. Guangdong Key Laboratory of Nanomedicine, Shenzhen Engineering Laboratory of Nanomedicine and Nanoformulations, CAS Key Laboratory of Health Informatics, Institute of Biomedicine and Biotechnology, Shenzhen Institutes of Advanced Technology, Chinese Academy of Sciences, Shenzhen 518055, P. R. China;
3. Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, Institute for Advanced Study, The Hong Kong University of Science and Technology, Hong Kong, P. R. China

Received:2020-10-28 Revised:2020-11-23 Online:2021-02-01 Published:2020-11-30
Contact: ZHANG Pengfei, GU Xinggui, TANG Ben Zhong E-mail:pf.zhang@siat.ac.cn;guxinggui@mail.buct.edu.cn;tangbenz@ust.hk
Supported by:
This work was partially supported by the National Natural Science Foundation of China(Nos.21702016, 21905015 and 52003023), and the Fund of the Beijing National Laboratory for Molecular Sciences, China(No.BNLMS201813). B. Z. Tang acknowledges the financial support from the National Natural Science Foundation of China(No.21788102), the Research Grants Council of Hong Kong(Nos. N_HKUT609/19, 16305518, and C6009-17G), and the Innovation and Technology Commission(No.ITC-CNERC14SC01).

摘要/Abstract

摘要： The development of fluorescent nanocrystals based on organic small molecules is of great importance in bioimaging due to the merits of easy modification, high brightness and excellent photostability, however suffering from the emission-detrimental aggregation-caused quenching(ACQ) effect. Herein, we successfully designed and synthesized an AIE-active di(N,N-dimethylaniline)-dibenzofulvene(named as NFTPE), which exhibits the crystallization-induced emission enhancement(CIEE) effect. Interestingly, two types of yellow- and orange-emissive crystals for NFTPE were obtained, exhibiting aggregation microenvironment-dependent emission tuning in the solid state. Single-crystal analysis and density functional theory(DFT) calculations reveal that different aggregation microenvironments result in the distinct molecular conformation for various emission. Excitingly, the crystallization of NFTPE in an aqueous solution under the assistance of amphiphilic PEG polymer matrices could be monitored in situ by the fluorescence changes, facilitating the preparation of NFTPE nanocrystals(NFTPE-NCs) by adjusting the aggregation microenvironment. The obtained NFTP-ENCs exhibit the superior performance in cell imaging in respect to high brightness, photostability, and biocompatibility, thus demon-strating the potential in bioimaging applications.

关键词: ggregation-induced emission(AIE), Crystallization-induced emission enhancement(CIEE), Aggregation microenviron-ment, Nanocrystal, Cell imaging

Abstract: The development of fluorescent nanocrystals based on organic small molecules is of great importance in bioimaging due to the merits of easy modification, high brightness and excellent photostability, however suffering from the emission-detrimental aggregation-caused quenching(ACQ) effect. Herein, we successfully designed and synthesized an AIE-active di(N,N-dimethylaniline)-dibenzofulvene(named as NFTPE), which exhibits the crystallization-induced emission enhancement(CIEE) effect. Interestingly, two types of yellow- and orange-emissive crystals for NFTPE were obtained, exhibiting aggregation microenvironment-dependent emission tuning in the solid state. Single-crystal analysis and density functional theory(DFT) calculations reveal that different aggregation microenvironments result in the distinct molecular conformation for various emission. Excitingly, the crystallization of NFTPE in an aqueous solution under the assistance of amphiphilic PEG polymer matrices could be monitored in situ by the fluorescence changes, facilitating the preparation of NFTPE nanocrystals(NFTPE-NCs) by adjusting the aggregation microenvironment. The obtained NFTP-ENCs exhibit the superior performance in cell imaging in respect to high brightness, photostability, and biocompatibility, thus demon-strating the potential in bioimaging applications.

Key words: ggregation-induced emission(AIE), Crystallization-induced emission enhancement(CIEE), Aggregation microenviron-ment, Nanocrystal, Cell imaging

YANG Liming, GUO Lixin, YU Hao, WANG Guan, SUN Jiangman, ZHANG Pengfei, GU Xinggui, TANG Ben Zhong. Organic Nanocrystals Based on a Solid-emission-tunable AIEgen for Cell Imaging[J]. 高等学校化学研究, 2021, 37(1): 129-136.

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Organic Nanocrystals Based on a Solid-emission-tunable AIEgen for Cell Imaging

Organic Nanocrystals Based on a Solid-emission-tunable AIEgen for Cell Imaging

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