Self-Complementary Dimers of Oxalamide-Functionalized Resorcinarene Tetrabenzoxazines

Zoran Džolić, Ngong Kodiah Beyeh, Mario Cetina, Lotta Turunen, Kari Rissanen*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

2 Citations (Scopus)

Abstract

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-HO and C-HO hydrogen bonds supplemented with C-Hπ interactions, forming one-dimensional polymers, which were then further linked into three-dimensional networks.

Original languageEnglish
Pages (from-to)164–169
JournalChemistry - An Asian Journal
Volume13
Issue number2
DOIs
Publication statusPublished - 2018
MoE publication typeA1 Journal article-refereed

Keywords

  • Dimers
  • Noncovalent interactions
  • Resorcinarenes
  • Supramolecular chemistry
  • X-ray diffraction

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