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Self‐Complementary Dimers of Oxalamide‐Functionalized Resorcinarene Tetrabenzoxazines
Author(s) -
Džolić Zoran,
Beyeh Ngong Kodiah,
Cetina Mario,
Turunen Lotta,
Rissanen Kari
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201701426
Subject(s) - resorcinarene , supramolecular chemistry , hydrogen bond , chemistry , amide , self assembly , intermolecular force , crystallography , supramolecular polymers , molecular recognition , polymer , polymer chemistry , crystal structure , molecule , organic chemistry
Self‐complementarity is a useful concept in supramolecular chemistry, molecular biology and polymeric systems. Two resorcinarene tetrabenzoxazines decorated with four oxalamide groups were synthesized and characterized. The oxalamide groups possessed self‐complementary hydrogen bonding sites between the carbonyls and amide groups. The self‐complementary nature of the oxalamide groups resulted in self‐included dimeric assemblies. The hydrogen bonding interactions within the tetrabenzoxazines gave rise to the formation of dimers, which were confirmed by single‐crystal X‐ray diffractions analysis and supported by NMR spectroscopy and mass spectrometry. The self‐included dimers were connected by numerous and strong intermolecular N−H⋅⋅⋅O and C−H⋅⋅⋅O hydrogen bonds supplemented with C−H⋅⋅⋅π interactions, forming one‐dimensional polymers, which were then further linked into three‐dimensional networks.