Selective Fluorescence Quenching of 2,3-Diazabicyclo[2.2.2]oct-2-ene by Nucleotides
- 25 September 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (21) , 3911-3914
Abstract
The fluorescence quenching of 2,3-diazabicyclo[2.2.2]oct-2-ene (DBO) by nucleotides has been studied. The quenching mechanism was analyzed on the basis of deuterium isotope effects, tendencies for exciplex formation, and the quenching efficiency in the presence of a molecular container (cucurbit[7]uril). Exciplex-induced quenching appears to prevail for adenosine, cytidine, and uridine, while hydrogen abstraction becomes competitive for thymidine and guanosine. Compared to other fluorescent probes, DBO responds very selectively to the type of nucleotide.Keywords
This publication has 28 references indexed in Scilit:
- Quenching of n,π*-Excited States in the Gas Phase: Variations in Absolute Reactivity and SelectivityJournal of the American Chemical Society, 2002
- Structure-reactivity relationships in the photoreduction of n,π*-excited ketones and azoalkanes: the effect of reaction thermodynamics, excited-state electrophilicity, and antibonding character in the transition statePhotochemical & Photobiological Sciences, 2002
- An Inorganic Tire-Tread Lattice: Hydrothermal Synthesis of the Layered Vanadate [N(CH3)4]5V18O46 with a Supercell StructureAngewandte Chemie International Edition, 1999
- PROTON-COUPLED ELECTRON TRANSFERAnnual Review of Physical Chemistry, 1998
- Catalytic, Highly Regio- and Chemoselective Generation of Radicals from Epoxides: Titanocene Dichloride as an Electron Transfer Catalyst in Transition Metal Catalyzed Radical ReactionsAngewandte Chemie International Edition, 1998
- Singlet Excited State Dynamics of Tetrakis(4-N-methylpyridyl)porphine Associated with DNA NucleotidesThe Journal of Physical Chemistry B, 1997
- Free Energy Dependence of Intermolecular Triplet Energy Transfer: Observation of the Inverted RegionThe Journal of Physical Chemistry, 1996
- Photoinduced electron transfer mediated by a hydrogen-bonded interfaceJournal of the American Chemical Society, 1992
- DNA sequencing, automation, and the human genomeAnalytical Chemistry, 1990
- Purine bases, nucleosides, and nucleotides: aqueous solution redox chemistry and transformation reactions of their radical cations and e- and OH adductsChemical Reviews, 1989