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A Highly Strained All‐Phenylene Conjoined Bismacrocycle
Author(s) -
Zhang Xinyu,
Shi Hong,
Zhuang Guilin,
Wang Shengda,
Wang Jinyi,
Yang Shangfeng,
Shao Xiang,
Du Pingwu
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202104669
Subject(s) - phenylene , crystallography , dihedral angle , torsion (gastropod) , chemistry , scanning tunneling microscope , benzene , materials science , ring (chemistry) , nanotechnology , molecule , hydrogen bond , anatomy , organic chemistry , biology , polymer
Herein, we report the precise synthesis of a 3D highly strained all‐phenylene bismacrocycle, termed conjoined (1,4)[10]cycloparaphenylenophane ( SCPP[10] ). This structure consists of a twisted benzene ring which is bridged twice by phenylene units anchored in two para‐positions. The conjoined structure of SCPP[10] was confirmed in real space at the atomic scale by scanning tunneling microscopy. Theoretical calculations indicate that this bismacrocycle has a very high strain energy of 110.59 kcal mol −1 and the largest interphenylene torsion angle of 46.07° caused by multiple repulsive interactions. Furthermore, a 1:2 host–guest complex of SCPP[10] and [6,6]‐phenyl‐C 61 ‐butyric acid methyl ester was investigated, which represents the first peanut‐shaped 1:2 host–guest complex based on bismacrocycles.