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-C61 -butyric acid methyl ester was investigated, which represents the first peanut-shaped 1:2 host-guest complex based on bismacrocycles.
Keywords: conjoined bismacrocycles; strained molecules; supramolecular interactions; twisted benzene.
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