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Synthesis and Photophysical Properties of [3]Cyclo-1,8-pyrenes via [4 + 2] Cycloaddition Reaction
Huiqing Liu1, Guilin Zhuang2, Shengda Wang1
1Hefei National Laboratory for Physical Sciences at Microscale, Key Laboratory of Materials for Energy Conversion, Chinese Academy of Sciences, Department of Materials Science and Engineering, iChEM, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui Province 230026, China.
Abstract:
Herein, we report the synthesis, characterization, and photophysical properties of the crown-like structure of [3]cyclo-1,8-pyrenes (compounds 9 and 10). Planar pyrenyl arylene-ethynylene macrocycles are used as the precursors to synthesize these pyrene-based cycloarenes by [4 + 2] cycloaddition reaction with good yields. These molecules are confirmed by nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. The structure of 9 was unambiguously determined by single-crystal X-ray diffraction. Their photophysical properties are investigated by steady-state absorption, fluorescence, and time-resolved fluorescence spectroscopies, combined with theoretical calculations.
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