title: Synthesis and energy-transfer properties of hydrogen-bonded oligofluorenes.
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.
authors.affiliation: Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The Netherlands.
authors.forename: Stephen P
authors.initials: SP
authors.lastname: Dudek
authors.forename: Maarten
authors.initials: M
authors.lastname: Pouderoijen
authors.forename: Robert
authors.initials: R
authors.lastname: Abbel
authors.forename: Albertus P H J
authors.initials: AP
authors.lastname: Schenning
authors.forename: E W
authors.initials: EW
authors.lastname: Meijer
mesh_terms: D002384:Catalysis; D005449:Fluorenes / Q000138:chemical synthesis / Q000737:chemistry; D006860:Hydrogen Bonding; D015394:Molecular Structure; D055095:Optics and Photonics; D010165:Palladium / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry; D011744:Pyrimidinones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D005449:Fluorenes; D011108:Polymers; D011744:Pyrimidinones; D010165:Palladium