A1 Journal article (refereed)
Self-Complementary Dimers of Oxalamide-Functionalized Resorcinarene Tetrabenzoxazines (2018)

Dzolic, Z., Beyeh, N. K., Cetina, M., Turunen, L., & Rissanen, K. (2018). Self-Complementary Dimers of Oxalamide-Functionalized Resorcinarene Tetrabenzoxazines. Chemistry: An Asian Journal, 13(2), 164-169. https://doi.org/10.1002/asia.201701426

JYU authors or editors

Dzolic, Zoran
Turunen, Lotta
Rissanen, Kari

Publication details

All authors or editors: Dzolic, Zoran; Beyeh, Ngong Kodiah; Cetina, Mario; Turunen, Lotta; Rissanen, Kari

Journal or series: Chemistry: An Asian Journal

ISSN: 1861-4728

eISSN: 1861-471X

Publication year: 2018

Volume: 13

Issue number: 2

Pages range: 164-169

Publisher: Wiley-VCH Verlag

Place of Publication: Weinheim

Publication country: Germany

Publication language: English

DOI: https://doi.org/10.1002/asia.201701426

Publication open access: Not open

Publication channel open access:

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/56809

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−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.

Keywords: oligomer; carbonyls; amides; spectroscopy; mass spectrometry; hydrogen; bonds