Synthesis and structural investigation of new triptycene-based ligands: en route to shape-persistent dendrimers and macrocycles with large free volume.
Triptycene was used to build a series of ligands containing pyrazine groups for use in forming coordination frameworks and as model compounds toward target shape-persistent dendrimers and macrocycles. The phenylenediamine precursors are formed by controlled double nitration/reduction of triptycene, followed by condensation with triptycenyl o-quinone to form the ligands. Solid-state structures show that the ligands favor packing in layered structures with intermolecular pi stacking. Increasing the length of the wings still allows for effective packing, but increasing the number of pyrazine groups or adding more triptycenyl moieties reduces packing efficiency. To demonstrate the potential of these molecules to function as ligands, a coordination complex of 15 with copper(I) iodide was obtained and found to form dimers that pack into a layered arrangement.
Chong
Jonathan H
JH
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, Canada.
MacLachlan
Mark J
MJ
D000873:Anthracenes / Q000138:chemical synthesis / Q000737:chemistry; D050091:Dendrimers / Q000138:chemical synthesis / Q000737:chemistry*; D008024:Ligands; D047028:Macrocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008958:Models, Molecular; D015394:Molecular Structure; D012015:Reference Standards; D013237:Stereoisomerism
D000873:Anthracenes; D050091:Dendrimers; D008024:Ligands; D047028:Macrocyclic Compounds; C520712:triptycene