Self-Complementary Dimers of Oxalamide-Functionalized Resorcinarene Tetrabenzoxazines
Dzolic, Zoran; Beyeh, Ngong Kodiah; Cetina, Mario; Turunen, Lotta; Rissanen, Kari (2018). Self-Complementary Dimers of Oxalamide-Functionalized Resorcinarene Tetrabenzoxazines. Chemistry: An Asian Journal, 13 (2), 164-169. DOI: 10.1002/asia.201701426
Published inChemistry: An Asian Journal
© 2018 Wiley-VCH Verlag GmbH & Co. This is a final draft version of an article whose final and definitive form has been published by Wiley. Published in this repository with the kind permission of the publisher.
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.