Quinoxaline-Based Polymer Dots with Ultrabright Red to Near-Infrared Fluorescence for In Vivo Biological Imaging
Abstract
This article describes the design and synthesis of quinoxaline-based semiconducting polymer dots (Pdots) that exhibit near-infrared fluorescence, ultrahigh brightness, large Stokes shifts, and excellent cellular targeting capability. We also introduced fluorine atoms and long alkyl chains into polymer backbones and systematically investigated their effect on the fluorescence quantum yields of Pdots. These new series of quinoxaline-based Pdots have a fluorescence quantum yield as high as 47% with a Stokes shift larger than 150 nm. Single-particle analysis reveals that the average per-particle brightness of the Pdots is at least 6 times higher than that of the commercially available quantum dots. We further demonstrated the use of this new class of quinoxaline-based Pdots for effective and specific cellular and subcellular labeling without any noticeable nonspecific binding. Moreover, the cytotoxicity of Pdots were evaluated on HeLa cells and zebrafish embryos to demonstrate their great biocompatibility. By taking advantage of their extreme brightness and minimal cytotoxicity, we performed, for the first time, in vivo microangiography imaging on living zebrafish embryos using Pdots. These quinoxaline-based NIR-fluorescent Pdots are anticipated to find broad use in a variety of in vitro and in vivo biological research.
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Fluorination minimizes structural distortions between the excited and ground states, which enhances the fluorescence quantum yield of Pdots.
“Thus, structural distortions between the excited and ground states are minimized by this substitution, which enhance the Φfl of Pdots.170,175,176”
From The Pursuit of Shortwave Infrared-Emitting Nanoparticles with Bright Fluorescence through Molecular Design and Excited-State Engineering of Molecular Aggregates (2022) · cites this paper as [176]
Fluorination introduces higher degrees of main-chain planarity, rigidity order, and packing tightness in conjugated polymers.
“In general, fluorination introduces higher degrees of main-chain planarity, rigidity order, and packing tightness.”
From The Pursuit of Shortwave Infrared-Emitting Nanoparticles with Bright Fluorescence through Molecular Design and Excited-State Engineering of Molecular Aggregates (2022) · cites this paper as [176]
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Self-citation
- Authors
- Liu, H.-Y., Wu, P.-J., Kuo, S.-Y., Chen, C.-P., Chang, E.-H., Wu, C.-Y., & Chan, Y.-H.
- Affiliations
- National Sun Yat-sen University (TW)
- Corresponding author
- Chan, Yang-Hsiang
- ORCID
- Chan, Yang-Hsiang
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2015-08-10
- Volume
- 137
- Issue
- 32
- Pages
- 10420-10429
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2411062454
- Cited by
- 181
- References
- 73
- Citations by year
- 2026: 4 · 2025: 4 · 2024: 11 · 2023: 10 · 2022: 13 · 2021: 14 · 2020: 26 · 2019: 22 · 2018: 24 · 2017: 34 · 2016: 16 · 2015: 3
- FWCI
- 10.41
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Taiwan University
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Quantum Dots Synthesis And Properties
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
- Keywords
- quinoxaline, polymer dots, semiconducting polymer dots, near-infrared fluorescence, red fluorescence, fluorescence quantum yield, Stokes shift, fluorine substitution, alkyl chain length, cell targeting, cytotoxicity, biocompatibility, zebrafish embryos, HeLa cells
- MeSH terms
- Animals, Embryo, Nonmammalian, Fluorescein Angiography, Fluorescence, Fluorine, HeLa Cells, Humans, Photochemistry, Quinoxalines, Semiconductors, Thiophenes, Zebrafish, Streptavidin, Quantum Dots, Chemistry Techniques, Synthetic, Optical Imaging, MCF-7 Cells
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