Synthesis and energy-transfer properties of hydrogen-bonded oligofluorenes.
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.
Dudek
Stephen P
SP
Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The Netherlands.
Pouderoijen
Maarten
M
Abbel
Robert
R
Schenning
Albertus P H J
AP
Meijer
E W
EW
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
D005449:Fluorenes; D011108:Polymers; D011744:Pyrimidinones; D010165:Palladium