A Mechanically Interlocked [3]Rotaxane as a Light-Harvesting Antenna: Synthesis, Characterization, and Intramolecular Energy Transfer

作者：Wang, Jie-Yu; Han, Ji-Min; Yan, Jing; Ma, Yuguo; Pei, Jian^*

来源：Chemistry - A European Journal, 2009, 15(14): 3585-3594.

DOI：10.1002/chem.200802228

• aggregation
• click chemistry
• cycloaddition
• energy transfer
• molecular devices
• oligo(phenylenevinylene)

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.

• 出版日期2009
• 单位北京大学