Urea-fused and π-extended single-benzene fluorophores with ultralarge Stokes shifts

The excited-state tautomer equilibrium of the urea-fused single-benzene fluorophore was synthetically modulated to produce exceptionally large Stokes shifts (>12 400 cm ). The key N-H⋯N hydrogen bonding motif utilizes an endogenous proton for long-wavelength emission or an exogenous proton for ac...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2024-08, Vol.60 (68), p.9105-9108
Main Authors: Choi, Taehyeon, Kim, Heechan, Kim, Younghun, Lee, Dongwhan
Format: Article
Language:English
Subjects:
Benzene
Chemical bonds
Chemical compounds
Hydrogen bonding
Protons
Ureas
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Summary:The excited-state tautomer equilibrium of the urea-fused single-benzene fluorophore was synthetically modulated to produce exceptionally large Stokes shifts (>12 400 cm ). The key N-H⋯N hydrogen bonding motif utilizes an endogenous proton for long-wavelength emission or an exogenous proton for acid-base chemistry, the balance of which is exploited for fluorescence switching in the solid state.
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d4cc03389b