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Alternating 2,6-/3,5-Substituted Pyridine-Acetylene Macrocycles: π-Stacking Self-Assemblies Enhanced by Intermolecular Dipole–Dipole Interaction
- Source :
- Organic Letters. 16:828-831
- Publication Year :
- 2014
- Publisher :
- American Chemical Society (ACS), 2014.
-
Abstract
- 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.
- Subjects :
- Macrocyclic Compounds
Molecular Structure
Acetylene
Pyridines
Hydrogen bond
Organic Chemistry
Intermolecular force
Stacking
Sonogashira coupling
Hydrogen Bonding
Crystallography, X-Ray
Biochemistry
chemistry.chemical_compound
Crystallography
Dipole
chemistry
Pyridine
Molecule
Physical and Theoretical Chemistry
Subjects
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 16
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi.dedup.....541c0884cf110274275edabb21884c90