Synthesis and energy-transfer properties of hydrogen-bonded oligofluorenes |
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Authors: | Dudek Stephen P Pouderoijen Maarten Abbel Robert Schenning Albertus P H J Meijer E W |
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Institution: | Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The Netherlands. |
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Abstract: | A set of fluorene oligomers has been synthesized by stepwise palladium-catalyzed (Suzuki) couplings of fluorene monomers. Ureidopyrimidinones (UPy), functional groups that can dimerize via quadruple hydrogen bonds, were attached to both ends of the oligofluorenes. The resulting bis-UPy-terminated oligomers self-assemble into supramolecular chain polymers. For comparison, oligofluorenes of the same oligomer lengths but without terminal hydrogen-bonding groups were synthesized. Chains of hydrogen-bonded fluorenes can be simply endcapped by a variety of chain stoppers, molecules that have one UPy group. In this manner, we have endcapped the hydrogen-bonded fluorene chains with either oligo(p-phenylenevinylene) or perylene bisimide. Energy-transfer experiments in solution and the solid state demonstrate that oligofluorenes can donate energy to a variety of energy acceptors, but that this energy transfer occurs most effectively when the donor fluorene is hydrogen-bonded to the acceptor. |
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