Expanding the chemical space of flavins with pentacyclic architecture
Abstract Inspired by the prominent redox and optical properties of natural flavins, synthetic flavins have found broad applications in organic, photochemical, and biochemical research. Tailoring these properties of flavins, however, remains a challenge. In this work, we present three pentacyclic fla...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2025-04-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-025-58957-2 |
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| author | Dayeong Seo Seongyeon Kwon Gahye Yoon Taeil Son Changhyeon Won Neetu Singh Dongwook Kim Yunjung Baek |
| author_facet | Dayeong Seo Seongyeon Kwon Gahye Yoon Taeil Son Changhyeon Won Neetu Singh Dongwook Kim Yunjung Baek |
| author_sort | Dayeong Seo |
| collection | DOAJ |
| description | Abstract Inspired by the prominent redox and optical properties of natural flavins, synthetic flavins have found broad applications in organic, photochemical, and biochemical research. Tailoring these properties of flavins, however, remains a challenge. In this work, we present three pentacyclic flavins (C-PF, O-PF, and S-PF) that leverage a strategic molecular design to modify the flavin’s electronic structure. Notably, the oxygen- and sulfur-linked pentacyclic flavins (O-PF and S-PF) exhibit deep-red and NIR emission, respectively, driven by enhanced π-conjugation, substituent effects, and charge separation upon excitation. These heteroatom-incorporated pentacyclic flavins exhibit unusual quasi-reversible oxidation, expanding both optical and redox limits of synthetic flavins. Comprehensive spectroscopic, structural, and computational analyses reveal how heteroatom incorporation within this five-ring-fused system unlocks redox and optical properties of flavin-derived chromophores. |
| format | Article |
| id | doaj-art-57a450aea9e94d03be87f3a7e987e095 |
| institution | DOAJ |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-04-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-57a450aea9e94d03be87f3a7e987e0952025-08-20T03:18:28ZengNature PortfolioNature Communications2041-17232025-04-0116111010.1038/s41467-025-58957-2Expanding the chemical space of flavins with pentacyclic architectureDayeong Seo0Seongyeon Kwon1Gahye Yoon2Taeil Son3Changhyeon Won4Neetu Singh5Dongwook Kim6Yunjung Baek7Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST)Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic ScienceDepartment of Chemistry, Korea Advanced Institute of Science and Technology (KAIST)Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST)Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST)Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST)Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic ScienceDepartment of Chemistry, Korea Advanced Institute of Science and Technology (KAIST)Abstract Inspired by the prominent redox and optical properties of natural flavins, synthetic flavins have found broad applications in organic, photochemical, and biochemical research. Tailoring these properties of flavins, however, remains a challenge. In this work, we present three pentacyclic flavins (C-PF, O-PF, and S-PF) that leverage a strategic molecular design to modify the flavin’s electronic structure. Notably, the oxygen- and sulfur-linked pentacyclic flavins (O-PF and S-PF) exhibit deep-red and NIR emission, respectively, driven by enhanced π-conjugation, substituent effects, and charge separation upon excitation. These heteroatom-incorporated pentacyclic flavins exhibit unusual quasi-reversible oxidation, expanding both optical and redox limits of synthetic flavins. Comprehensive spectroscopic, structural, and computational analyses reveal how heteroatom incorporation within this five-ring-fused system unlocks redox and optical properties of flavin-derived chromophores.https://doi.org/10.1038/s41467-025-58957-2 |
| spellingShingle | Dayeong Seo Seongyeon Kwon Gahye Yoon Taeil Son Changhyeon Won Neetu Singh Dongwook Kim Yunjung Baek Expanding the chemical space of flavins with pentacyclic architecture Nature Communications |
| title | Expanding the chemical space of flavins with pentacyclic architecture |
| title_full | Expanding the chemical space of flavins with pentacyclic architecture |
| title_fullStr | Expanding the chemical space of flavins with pentacyclic architecture |
| title_full_unstemmed | Expanding the chemical space of flavins with pentacyclic architecture |
| title_short | Expanding the chemical space of flavins with pentacyclic architecture |
| title_sort | expanding the chemical space of flavins with pentacyclic architecture |
| url | https://doi.org/10.1038/s41467-025-58957-2 |
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