Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 14, Pages 3585-3594Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200802228
Keywords
aggregation; click chemistry; cycloaddition; energy transfer; molecular devices; oligo(phenylenevinylene)
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Funding
- Major State Basic Research Development Program [2006CB921602, 2007CB808000]
- Ministry of Science and Technology
- National Natural Science Foundation of China
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A mechanically interlocked light-harvesting system [3]rotaxane A has been synthesized in high yield through Cu(I)-catalyzed azide-alkyne cycloaddition; the hexyl-substituted truxene units are introduced into the wheels as donors and an oligo(paraphenylenevinylene) (OPV) unit into the axis as the acceptor. The structure and the purity of [3]rotaxane A were confirmed by H-1 and C-13 NMR spectroscopy and ESI HRMS. The azide-alkyne cycloaddition is demonstrated to be an efficient stoppering method in the synthesis of the rotaxane containing dibenzo[24]crown-8 and dibenzyl ammonium units. Detailed steady-state UV/Vis absorption, photoluminescent, and time-resolved fluorescence spectroscopy were performed to investigate the photophysical properties of [3]rotaxane A and its reference compounds in solution and as thin films. Even in dilute solution, efficient energy transfer from the truxene-functionalized wheels to the OPV-based axis, through the dibenzo[24]crown-8 and dibenzyl ammonium interaction, is observed in [3]rotaxane A. The unique topology of [3]rotaxane A not only efficiently promotes the intramolecular energy-transfer process, but also prevents intermolecular aggregation in the solid state. The new antenna system opens up the possibility of controllable light-harvesting molecular machines or other optoelectronic devices on the nanometer scale.
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