Abstract
Mono- and bifunctional oligo(p-phenylene vinylene)s (OPVs) functionalized with ureido-s-triazine units have been synthesized and fully characterized. In chloroform monofunctional OPV derivatives dimerize with a dimerization constant of Kdim = (2.1 ± 0.3) × 104 L/mol, while bifunctional OPV derivatives are present as random coil polymers in this solvent. In more apolar solvents such as dodecane, the hydrogen-bonded dimers of the monofunctional OPV derivative aggregate in chiral stacks, as can be concluded from UV/vis, fluorescence and CD spectroscopy. Temperature-dependent measurements show a first-order transition at 53 ± 3 °C from the aggregated state to the molecularly dissolved phase. The bifunctional derivative also aggregates in dodecane; however, based on CD measurements, these aggregates are less organized. This behavior is presumably the outcome of a competition between favorable π−π interactions and restricted conformational freedom, due to the hexyl spacer, which results in a frustrated supramol...
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