An Aromatic Oligomer Micelle: Large Enthalpic Stabilization and Selective Oligothiophene Uptake.

An aromatic oligomer micelle, featuring both high stability and high uptake ability, was quantitatively formed in water from amphiphilic oligomers, composed of three bent polyaromatic amphiphiles connected alternately by two hydrophilic chains. The well-defined micelle, with a diameter of ca. 2 nm, remains intact even under highly diluted conditions (ca. 3 μM) and at elevated temperature (>130 °C), due to the polyaromatic chelate effect. The thermodynamic studies reveal that large enthalpic gain (ΔH=-110 kJ mol-1 ) is the key for the micelle formation. The oligomer micelle selectively encapsulates unsubstituted oligothiophenes (≥4-mer) to a high degree and the resultant, aqueous host-guest complexes display unusual emission derived from the multiply stacked oligomers. Furthermore, facile uptake and release of unsubstituted polythiophenes can be achieved using the oligomer micelle.