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Synthesis and Characterization of a Pentiptycene‐Derived Dual Oligoparaphenylene Nanohoop
Author(s) -
Xu Wei,
Yang XiaoDi,
Fan XiangBing,
Wang Xin,
Tung ChenHo,
Wu LiZhu,
Cong Huan
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201814482
Subject(s) - characterization (materials science) , molecule , enantiomer , ring (chemistry) , cycloaddition , dual (grammatical number) , solid state , chemistry , resolution (logic) , materials science , combinatorial chemistry , crystal structure , nanotechnology , stereochemistry , crystallography , computer science , organic chemistry , catalysis , art , literature , artificial intelligence
Structural designs combining oligoparaphenylene‐derived nanohoops with other functional organic building blocks should lead to novel molecular architectures with intriguing properties. Herein, we describe the synthesis of a pentiptycene‐derived chiral dual nanohoop molecule with key steps including ring expansion through dianthracene cycloreversion and transannular [4+2] cycloaddition across a 64‐membered macrocycle. The crystal structure of the nanohoop molecule displays an ordered packing pattern with long‐range channels in the solid state. Furthermore, nonracemizable enantiomers of the nanohoop were obtained through resolution and exhibited promising chiroptical properties.