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Synthesis of a Hemispherical Geodesic Phenine Framework by a Polygon Assembling Strategy
Author(s) -
Mio Tatsuru,
Ikemoto Koki,
Sato Sota,
Isobe Hiroyuki
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201915509
Subject(s) - geodesic , bridging (networking) , molecule , crystallography , torsion (gastropod) , chemistry , chemical physics , materials science , molecular physics , geometry , computer science , mathematics , organic chemistry , medicine , computer network , surgery
A synthetic strategy to construct large geodesic structures of phenine (1,3,5‐trisubstituted benzene) was devised. In this strategy, five pentagons were assembled on an omphalos pentagon, and bridging peripheral pentagons furnished five additional hexagons. Thirty phenine units were synthetically assembled to afford a large C 220 H 180 molecule with a phenine framework isoreticular to a hemispherical, bisected segment of C 60 . Although a hemispherical structure of the phenine framework was suggested by solution‐phase NMR spectra, crystallographic analysis revealed an oval‐like deformation of the molecular shape. In‐depth structural analyses, including theoretical calculations, showed that structural fluctuations observed as variations in the biaryl torsion angles allowed structural deformations and, at the same time, that the dynamic fluctuations resulted in the spectroscopic observation of a hemisphere as a time‐averaged structure.