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 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 spect

SUBMITTER: Seo D 

PROVIDER: S-EPMC12000593 | biostudies-literature | 2025 Apr

REPOSITORIES: biostudies-literature