Phase-transfer-catalyst enabled enantioselective C–N coupling to access chiral boron-stereogenic BODIPYs
Abstract Tetracoordinate boron-based fluorescent materials have shown extensively applications in chemistry, biology and materials science owing to their unique optoelectronic properties. However, constructing chiral boron-stereogenic fluorophores through practical and universal strategies remains r...
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Nature Portfolio
2025-03-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-025-58117-6 |
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| author | Xue-Qing Zhang Xiao-Juan Lv Luying Guo Juan Ma Bin Su Yuefei Hu Lijuan Jiao Zhong-Yuan Li Erhong Hao |
| author_facet | Xue-Qing Zhang Xiao-Juan Lv Luying Guo Juan Ma Bin Su Yuefei Hu Lijuan Jiao Zhong-Yuan Li Erhong Hao |
| author_sort | Xue-Qing Zhang |
| collection | DOAJ |
| description | Abstract Tetracoordinate boron-based fluorescent materials have shown extensively applications in chemistry, biology and materials science owing to their unique optoelectronic properties. However, constructing chiral boron-stereogenic fluorophores through practical and universal strategies remains rare and challenging. Herein, as a proof of concept, we report an enantioselective postfunctionalization of boron dipyrromethene dyes (BODIPYs), to acess boron-stereogenic BODIPYs in moderate to good yields with commendable enantioselectivity. Chiral BODIPYs have attracted increasing attention owing to not only their distinctively photophysical properties and applications in circularly polarized luminescence (CPL) materials, but also diversely structural modification. In this·work, we present a phase-transfer-catalyst enabled enantioselective C–N coupling reaction of BODIPYs with diverse nucleophiles. This method serves as a practical SNAr (nucleophilic aromatic substitution reaction) route to achieve a series of boron-stereogenic amido/amino BODIPYs as well as demonstrates their promising CD and·CPL·activities, excellent biocompatibility, and high specificities, showing potential applications as chiral fluorescent imaging agents. |
| format | Article |
| id | doaj-art-a547ab7768f94bd8818e3f90c83b5bbf |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-a547ab7768f94bd8818e3f90c83b5bbf2025-08-20T03:41:49ZengNature PortfolioNature Communications2041-17232025-03-0116111010.1038/s41467-025-58117-6Phase-transfer-catalyst enabled enantioselective C–N coupling to access chiral boron-stereogenic BODIPYsXue-Qing Zhang0Xiao-Juan Lv1Luying Guo2Juan Ma3Bin Su4Yuefei Hu5Lijuan Jiao6Zhong-Yuan Li7Erhong Hao8Anhui Laboratory of Molecule-Based Materials, School of Chemistry and Materials Science, Anhui Normal UniversityAnhui Laboratory of Molecule-Based Materials, School of Chemistry and Materials Science, Anhui Normal UniversityAnhui Laboratory of Molecule-Based Materials, School of Chemistry and Materials Science, Anhui Normal UniversityAnhui Laboratory of Molecule-Based Materials, School of Chemistry and Materials Science, Anhui Normal UniversityAnhui Laboratory of Molecule-Based Materials, School of Chemistry and Materials Science, Anhui Normal UniversityAnhui Laboratory of Molecule-Based Materials, School of Chemistry and Materials Science, Anhui Normal UniversityAnhui Laboratory of Molecule-Based Materials, School of Chemistry and Materials Science, Anhui Normal UniversityAnhui Laboratory of Molecule-Based Materials, School of Chemistry and Materials Science, Anhui Normal UniversityAnhui Laboratory of Molecule-Based Materials, School of Chemistry and Materials Science, Anhui Normal UniversityAbstract Tetracoordinate boron-based fluorescent materials have shown extensively applications in chemistry, biology and materials science owing to their unique optoelectronic properties. However, constructing chiral boron-stereogenic fluorophores through practical and universal strategies remains rare and challenging. Herein, as a proof of concept, we report an enantioselective postfunctionalization of boron dipyrromethene dyes (BODIPYs), to acess boron-stereogenic BODIPYs in moderate to good yields with commendable enantioselectivity. Chiral BODIPYs have attracted increasing attention owing to not only their distinctively photophysical properties and applications in circularly polarized luminescence (CPL) materials, but also diversely structural modification. In this·work, we present a phase-transfer-catalyst enabled enantioselective C–N coupling reaction of BODIPYs with diverse nucleophiles. This method serves as a practical SNAr (nucleophilic aromatic substitution reaction) route to achieve a series of boron-stereogenic amido/amino BODIPYs as well as demonstrates their promising CD and·CPL·activities, excellent biocompatibility, and high specificities, showing potential applications as chiral fluorescent imaging agents.https://doi.org/10.1038/s41467-025-58117-6 |
| spellingShingle | Xue-Qing Zhang Xiao-Juan Lv Luying Guo Juan Ma Bin Su Yuefei Hu Lijuan Jiao Zhong-Yuan Li Erhong Hao Phase-transfer-catalyst enabled enantioselective C–N coupling to access chiral boron-stereogenic BODIPYs Nature Communications |
| title | Phase-transfer-catalyst enabled enantioselective C–N coupling to access chiral boron-stereogenic BODIPYs |
| title_full | Phase-transfer-catalyst enabled enantioselective C–N coupling to access chiral boron-stereogenic BODIPYs |
| title_fullStr | Phase-transfer-catalyst enabled enantioselective C–N coupling to access chiral boron-stereogenic BODIPYs |
| title_full_unstemmed | Phase-transfer-catalyst enabled enantioselective C–N coupling to access chiral boron-stereogenic BODIPYs |
| title_short | Phase-transfer-catalyst enabled enantioselective C–N coupling to access chiral boron-stereogenic BODIPYs |
| title_sort | phase transfer catalyst enabled enantioselective c n coupling to access chiral boron stereogenic bodipys |
| url | https://doi.org/10.1038/s41467-025-58117-6 |
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