Alternating 2,6-/3,5-substituted pyridine-acetylene macrocycles: π-stacking self-assemblies enhanced by intermolecular dipole-dipole interaction.
Macrocyclic compounds consisting of three 2,6-pyridylene and three 3,5-pyridylene units linked by acetylene bonds were synthesized by a Sonogashira reaction. The X-ray structures showed π-stacked pairs of two macrocycles, in which a 2,6-pyridylene unit of the one molecule overlaps a 3,5-pyridylene of the other molecule because of dipole-dipole interaction. Atomic force microscope (AFM) measurements revealed fibril structures indicating the stacking of the rigid planar macrocycles. Hydrogen-bonding ability of the macrocyclic inside was demonstrated by the addition of octyl β-D-glucopyranoside.
Graduate School of Pharmaceutical Sciences, University of Toyama , Toyama 930-0194, Japan.
Hajime
H
Abe
Kohei
K
Ohtani
Daiki
D
Suzuki
Yusuke
Y
Chida
Yuta
Y
Shimada
Shinya
S
Matsumoto
Masahiko
M
Inouye
D000114:Acetylene / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*
D047028:Macrocyclic Compounds; D011725:Pyridines; C023666:pyridine; D000114:Acetylene