Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 12, Pages 4785-4792Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201915744
Keywords
amines; charge transfer; donor-acceptor systems; fluorescence; solvent effects
Categories
Funding
- BurroughsWellcome Fund Career Award at the Scientific Interface
- Paul Berg Early Career Professorship
- Lloyd and Dottie Huck Early Career Award
- Sloan Research Fellowship
- PEW Biomedical Scholars Program
- NSF [CHE-1856210]
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While organic donor-acceptor (D-A) molecules are widely employed in multiple areas, the application of more D-A molecules could be limited because of an inherent polarity sensitivity that inhibits photochemical processes. Presented here is a facile chemical modification to attenuate solvent-dependent mechanisms of excited-state quenching through addition of a beta-carbonyl-based polar substituent. The results reveal a mechanism wherein the beta-carbonyl substituent creates a structural buffer between the donor and the surrounding solvent. Through computational and experimental analyses, it is demonstrated that the beta-carbonyl simultaneously attenuates two distinct solvent-dependent quenching mechanisms. Using the beta-carbonyl substituent, improvements in the photophysical properties of commonly used D-A fluorophores and their enhanced performance in biological imaging are shown.
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