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Organic nanosynthesis of diarylfluorene-based ladder-type gridarene isomers via intramolecular A1-B1 type Friedel-Crafts gridization
Authors:Sixian Sun  Changjin Ou  Dongqing Lin  Zongyan Zuo  Yong Yan  Ying Wei  Yuyu Liu  Linghai Xie  Wei Huang
Institution:1. Center for Molecular Systems and Organic Devices (CMSOD), Key Laboratory for Organic Electronics and Information Displays (KLOEID) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing University of Posts & Telecommunications, Nanjing 210046, China;2. School of Physical and Mathematical Sciences, Nanjing Tech University (NanjingTech), Nanjing 211816, China;3. Shaanxi Institute of Flexible Electronics (SIFE), Northwestern Polytechnical University (NPU), 127 West Youyi Road, Xi''an 710072, Shaanxi, China
Abstract:Fluorene-based ladder-type nanogrids have been synthesized via the stepwise and iterative Friedel-Crafts/Suzuki cross-coupling reactions, and efficient intramolecular gridization reaction could enhance yield up to ~95%. Multiple configurational isomers were successfully separated with the yield of 10%, 20% and 65% for Grid-DFCz-1, Grid-DFCz-2 and Grid-DFCz-3 respectively. The molecular configurations of Grid-arene isomers were characterized and confirmed by the NMR spectra. We found that molecular configuration has little influence on photophysical and electrochemical properties.
Keywords:Solution-processed nanogrid  Diarylfluorene  Ladder-type  Configurational isomers  Intramolecular Friedel-Crafts reaction
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