Self-assembly of supramolecular oligo-phenylene-ethynylene wires consisting of double Hamilton receptor modified OPE rods and a tetraphenylporphyrin cyanurate

The syntheses and characterizations of new oligo-phenylene-ethynylene (OPE) bridged bis-Hamilton receptors 8–9 and their linear H-bonding behaviour with a new cyanuric acid modified tetraphenylporphyrin (TPP) 13 are reported. The resulting rigid complexes consisting of an oligo-phenylene-acetylene wire and two terminating TPPs were characterized by 1H NMR, UV/vis and fluorescence spectroscopies. The 1:2 compositions of the supramolecular complexes, the association constants Kn and the cooperativity of binding expressed by Scatchard plots and Hill coefficients ηH were determined by 1H NMR titration experiments. The strength of the association constants Kn in CDCl3 at rt was found to be in a range of 105 and 106 mol−1 dm3 for the first complexation and 1010–1012 mol−1 dm3 for the second complexation, which is rather strong.