期刊
ACS SENSORS
卷 1, 期 2, 页码 158-165出版社
AMER CHEMICAL SOC
DOI: 10.1021/acssensors.5b00065
关键词
BODIPY dye; morpholine moiety; intracellular pH; photoinduced electron transfer (PET)
资金
- National Institute of General Medical Sciences of the National Institutes of Health [R15GM114751]
- National Science Foundation [1048655]
- Michigan Technological University faculty start-up fund
- Research Excellence Fund
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1048655] Funding Source: National Science Foundation
Three uncommon morpholine-based fluorescent probes (A, B, and C) for pH were prepared by introducing morpholine residues to BODIPY dyes at 4,4'- and 2,6-positions, respectively. In contrast to morpholine-based fluorescent probes for pH reported in literature, these fluorescent probes display high fluorescence in a basic condition while they exhibit very weak fluorescence in an acidic condition. The theoretical calculation confirmed that morpholine is unable to function as either an electron donor or an electron acceptor to quench the BODIPY fluorescence in the neutral and basic condition via photoinduced electron transfer PET) mechanism because the LUMO energy of morpholine is higher than those of the BODIPY dyes while its HOMO energy is lower than those of the BODIPY dyes. However, the protonation of tertiary amines of the morpholine residues in an acidic environment leads to fluorescence quenching of the BODIPY dyes via d-PET mechanism. The fluorescence quenching is because the protonation effectively decreases the LUMO energy which locates between the HOMO and LUMO energies of the BODIPY dyes. Fluorescent probe C with deep-red emission has been successfully used to detect pH changes in mammalian cells.
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