3,4-Ethylenedithio thiophene donor for NIR-II fluorophores with improved quantum yields

Liu，Chunchen1,2; Wang，Xinyuan2; Zhu，Xingfu2; Ma，Rui2; Lin，Qihui1; Liang，Yongye2

2023

10.1039/d2qm01278b

Materials Chemistry Frontiers   Impact Factor & Quartile

2052-1537

Bright fluorophores are vital for bioimaging in the second near-infrared (NIR-II, 1500-1700 nm) window. Donor engineering has been demonstrated to be effective at significantly improving the brightness of donor-acceptor-donor (D-A-D) NIR-II fluorophores. Developing new donor units to construct NIR-II fluorophores with improved quantum yields (QYs) is still challenging. Herein, 3,4-ethylenedithio thiophene (EDST) is employed as the donor unit for the first time to construct a new NIR-II fluorophore, IR-nFES. Compared with the fluorophore IR-nFE with the 3,4-ethylenedioxy thiophene (EDOT) donor, sulphur atom replacement can significantly increase the conjugation backbone distortion, affording an enhanced fluorescence QY of 5.5% in toluene for IR-nFES. Water soluble nanofluorophores (NFs) of IR-nFES are fabricated by encapsulating with an amphiphilic copolymer, and IR-nFE NFs show a QY of 1.3%, 4.8 times higher than that of the IR-nFE counterpart. It is further demonstrated that IR-nFES NFs are significantly brighter than IR-nFE NFs and indocyanine green (ICG), and also exhibit good optical stability. Consequently, IR-nFES NFs realize superior in vivo imaging of mouse cerebral vessels with a high signal-to-background ratio (SBR) of 4.99. Our studies reveal that sulphur substitution can afford new NIR-II molecular fluorophores with enhanced brightness.

SCI

English

Corresponding

National Natural Science Foundation of China[21772084] ; Fundamental Research Layout of Shenzhen[JCYJ20180504165657443] ; Guangdong Provincial Natural Science Foundation[2019A1515110464] ; Shenzhen San-Ming Project[SZSM201809085] ; Shenzhen Science and Technology Commission-free exploration/general project[JCYJ20190812151209348]

Chemistry ; Materials Science

Chemistry, Multidisciplinary ; Materials Science, Multidisciplinary

WOS:000961001600001

ROYAL SOC CHEMISTRY

2-s2.0-85151838811

Scopus

1.Joint Laboratory for Infectious Disease Prevention and Control,Hygienic Section of Longhua Center for Disease Control and Prevention,Shenzhen,Longhua District,518109,China
2.Department of Materials Science and Engineering,Shenzhen Key Laboratory of Printed Organic Electronic,Southern University of Science and Technology,Shenzhen,518055,China

Liu，Chunchen,Wang，Xinyuan,Zhu，Xingfu,et al. 3,4-Ethylenedithio thiophene donor for NIR-II fluorophores with improved quantum yields[J]. Materials Chemistry Frontiers,2023.

Liu，Chunchen,Wang，Xinyuan,Zhu，Xingfu,Ma，Rui,Lin，Qihui,&Liang，Yongye.(2023).3,4-Ethylenedithio thiophene donor for NIR-II fluorophores with improved quantum yields.Materials Chemistry Frontiers.

Liu，Chunchen,et al."3,4-Ethylenedithio thiophene donor for NIR-II fluorophores with improved quantum yields".Materials Chemistry Frontiers (2023).