Journal
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
Volume 18, Issue 38, Pages 26703-26711Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6cp02423h
Keywords
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Funding
- Russian Foundation for Basic Research [15-03-02856-a]
- National Science Foundation [CHE-1213047]
- Australian Research Council (ARC) [DP110101580, DP160102425]
- Australian National Computational Infrastructure Facility at ANU [m03, n62]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1213047] Funding Source: National Science Foundation
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We report the synthesis and characterization of a pH-sensitive fluorescence switch based on a conformationally-locked green fluorescent protein (GFP) chromophore. The chromophore differs from difluoroboryl-locked parent by the addition of a titratable alcohol group on the imidazolinone ring. The chromophore is fluorescent at pH <= 5, but becomes non-fluorescent at higher pH, where the substituent is ionized. We use a quantum chemical model to show that the mechanism of the fluorescence turn-off is electronically analogous to photochemical meta effects in aryl-containing systems.
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