Spontaneous self-assembly of water-soluble nucleotide-calixarene conjugates in small micelles coalescing to microspheres

Spontaneous self-assembly of calix[4]arenes bearing four 2'-deoxythymidine or 2'-deoxyadenosine nucleotide pendants is investigated using (1)H NMR, exchange NMR, and diffusion ordered NMR spectroscopies and dynamic light scattering. In aqueous medium, the nucleotide-calixarene conjugates, by noncovalent interactions involving both nucleobases and calixarene skeleton, form dimers which self-organize in micelles by increasing the concentration. Microscopic images (scanning electron microscopy and transmission electron microscopy) show that the nucleobase affects the aggregate morphology in the solid state.