A computational and experimental investigation of donor-acceptor BODIPY based near-infrared fluorophore for in vivo imaging
Abstract
TD-DFT quantum calculation was performed to predict and/or illustrate the electronic transition, the related absorption and emission maxima of some pyrrole-difluoroboron derivatives with different electron donor-acceptor unit or π-conjugated degree. Upon the calculated results, a new near infrared (NIR) fluorophore (abbreviated as TPBD-BP) was designed and fabricated through linking triphenylamine and pyrrole-difluoroboron units to benzothiadiazole (BTD) backbone. The fluorescence of TPBD-BP in solid state centered at 932 nm, which was 985 nm for TPBD-BP nanoparticles (TPBD-BP dots) encapsulated in PEG-6000. The fluorescence of TPBD-BP in both solid state and dots exhibited off-peak tail emission to NIR-II region (extended to 1300 nm). The TPBD-BP dots showed excellent water solubility, biocompatibility and aggregation induced emission (AIE), which was suitable to be applied in vivo imaging. NIR-II emission signal of TPBD-BP dots can be observed in the reproductive organ of normal nude mice after tail vein injection. This attractive combination of computational and experimental investigation would help to develop new-typed small-molecular NIR fluorophores.
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Tail fluorescence emission sometimes allows high-contrast imaging with current organic SWIR fluorophores.
“This tail fluorescence emission sometimes allows high-contrast imaging with current organic SWIR fluorophores.29,34,96,219,220”
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 [219]
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- Authors
- Zhang, R., He, X., Jiang, J.-M., Li, P.-P., Wang, H.-Y., Li, L., Yang, J.-X., & Kong, L.
- Affiliations
- Anhui University (CN)
- Northwestern Polytechnical University (CN)
- Corresponding author
- Kong, Lin
- Venue
- Bioorganic Chemistry
- Publisher
- Elsevier BV
- Published
- 2021-05
- Volume
- 110
- Pages
- 104789
- ISSN
- 0045-2068 (ISSN-L)
- OpenAlex
- W3135481010
- Cited by
- 7
- References
- 51
- Citations by year
- 2026: 1 · 2025: 2 · 2024: 1 · 2023: 1 · 2022: 2
- FWCI
- 0.30
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- Bioorganic Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
- Physical Sciences › Chemistry › Organic Chemistry › Organoboron and organosilicon chemistry
- Keywords
- BODIPY, donor-acceptor fluorophores, triphenylamine, aggregation-induced emission, in vivo imaging, water-soluble nanoparticles, biocompatibility
- MeSH terms
- Density Functional Theory, Animals, Boron Compounds, Fluorescent Dyes, Infrared Rays, Mice, Nude, Thiadiazoles, Molecular Structure, Mice, Optical Imaging
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