Effect of chromophore-charge distance on the energy transfer properties of water-soluble conjugated oligomers
| Autor: | Brent S. Gaylord, Bin Liu, Shu Wang, Guillermo C. Bazan |
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| Rok vydání: | 2003 |
| Předmět: |
Stereochemistry
Kinetics Fluorescence spectrometry DNA Single-Stranded Conjugated system Biochemistry Medicinal chemistry Catalysis Hydrophobic effect Colloid and Surface Chemistry Side chain Benzene Derivatives Fluorescence Resonance Energy Transfer Fluorescent Dyes Quenching (fluorescence) Chemistry Cationic polymerization Nucleic Acid Hybridization Water General Chemistry DNA Chromophore Quaternary Ammonium Compounds Solubility Fluorescein Hydrophobic and Hydrophilic Interactions |
| Zdroj: | Journal of the American Chemical Society. 125(22) |
| ISSN: | 0002-7863 |
| Popis: | The synthesis of 1,4-bis(9,9'-bis(3"-(N,N,N-trimethylammonium)-propyl)-2'-fluorenyl)benzene tetrabromide (C3), 1,4-bis(9,9'-bis(4"-(N,N,N-trimethylammonium)-butyl)-2'-fluorenyl)benzene tetrabromide (C4), 1,4-bis(9,9'-bis(6"-(N,N,N-trimethylammonium)-hexyl)-2'-fluorenyl)benzene tetrabromide (C6), and 1,4-bis(9,9'-bis(8"-(N,N,N-trimethylammonium)-octyl)-2'-fluorenyl)benzene tetrabromide (C8) is reported. Fluorescence energy transfer experiments between C3-C8 and the acceptors pentasodium 1,4-bis(4'(2",4"-bis(butoxysulfonate)-styryl)styryl)-2-(butoxysulfonate)-5-methoxybenzene (3), fluorescein labeled single-stranded DNA and fluorescein labeled double-stranded DNA in water, buffer, and methanol reveal the importance of hydrophobic and electrostatic forces in determining chromophore-chromophore close proximity. In water, the oligomers with longer side chain length show better energy transfer, as well as higher Stern-Volmer quenching constants (K(sv)), largely due to a stronger hydrophobic attraction between the optically active components. In methanol, the differences in energy transfer are leveled, and the oligomers with shorter side chain lengths show higher K(sv) values. Compounds C3, C4, C6, and C8 were also used to dissect the different contributors to DNA hybridization assays based on cationic conjugated polymers. |
| Databáze: | OpenAIRE |
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