Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 4, Pages 863-872Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201904164
Keywords
BODIPY; confocal fluorescence microscopy; fluorophores; lipid bilayers; near-infrared; structure-property relationships
Categories
Funding
- Leverhulme Trust [RPG-2019-183, RPG-2017-015]
- EPSRC [EP/N026322/1, EP/N026411/1]
- ERC [769798]
- European Research Council (ERC) [769798] Funding Source: European Research Council (ERC)
- EPSRC [EP/N026411/1, EP/K005030/1, EP/P020410/1, EP/N026322/1] Funding Source: UKRI
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Designing chromophores for biological applications requires a fundamental understanding of how the chemical structure of a chromophore influences its photophysical properties. We here describe the synthesis of a library of BODIPY dyes, exploring diversity at various positions around the BODIPY core. The results show that the nature and position of substituents have a dramatic effect on the spectroscopic properties. Substituting in a heavy atom or adjusting the size and orientation of a conjugated system provides a means of altering the spectroscopic profiles with high precision. The insight from the structure-activity relationship was applied to devise a new BODIPY dye with rationally designed photochemical properties including absorption towards the near-infrared region. The dye also exhibited switch-on fluorescence to enable visualisation of cells with high signal-to-noise ratio without washing-out of unbound dye. The BODIPY-based probe is non-cytotoxic and compatible with staining procedures including cell fixation and immunofluorescence microscopy.
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