Trianglamines--readily prepared, conformationally flexible inclusion-forming chiral hexamines.
Trianglamines, macrocyclic heteraphanes, were readily synthesised through a [3+3] cyclocondensation of (R,R)-1,2-diaminocyclohexane with terephthalaldehyde, followed by NaBH4 reduction and N-alkylation. The macrocyclic ring shows a remarkable ability to change its conformation, as a consequence of rotation about the C-N bonds or nitrogen inversion due to protonation or N-alkylation, as revealed by circular dichroism spectra, computational modelling and X-ray diffraction analysis. The flexible natures of the trianglamine macrocycles allow ready accommodation of a variety of guest molecules to form crystalline inclusion complexes of highly diversified interpenetrating structures.
Gawronski
Jacek
J
Department of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60780 Poznan, Poland. gawronsk@amu.edu.pl
Gawronska
Krystyna
K
Grajewski
Jakub
J
Kwit
Marcin
M
Plutecka
Agnieszka
A
Rychlewska
Urszula
U
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D000588:Amines; D006571:Heterocyclic Compounds; D007202:Indicators and Reagents