Synthesis and Structural Investigation of New Triptycene-Based Ligands: En Route to Shape-Persistent Dendrimers and Macrocycles with Large Free Volume
- 11 October 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 72 (23) , 8683-8690
Abstract
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 π 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.Keywords
This publication has 27 references indexed in Scilit:
- Tailoring Porphyrins and Chlorins for Self-Assembly in Biomimetic Artificial Antenna SystemsAccounts of Chemical Research, 2005
- Past, present and futute of cyclodextrin researchPure and Applied Chemistry, 2004
- Synthesis and Solid-State Organization of Coil–Ring–Coil Block CopolymersChemistry – A European Journal, 2003
- Synthesis, Aggregation, and Adsorption Phenomena of Shape-Persistent Macrocycles with Extraannular Polyalkyl SubstituentsJournal of the American Chemical Society, 2001
- Novel phthalocyanine‐based conductors: tunable Π–Π stacking structure through the steric and chemical interactions of axial ligandsJournal of Porphyrins and Phthalocyanines, 2001
- Solvophobically Driven π-Stacking of Phenylene Ethynylene Macrocycles and OligomersJournal of the American Chemical Society, 2000
- Mesomorphic phthalocyanines, tetraazaporphyrins, porphyrins and triphenylenes as charge-transporting materialsJournal of Porphyrins and Phthalocyanines, 2000
- Expanded Porphyrins and Their HeterologsChemical Reviews, 1997
- Self‐assembled wires and channelsAdvanced Materials, 1996
- Direct electron transfer involving free-solute ferrocene in fluid electrolyte on an oxocuprate (Bi(Pb) 2223) electrode in the superconducting stateJournal of the American Chemical Society, 1992