Self-assembling building blocks that are readily functionalizable and capable of achieving programmed hierarchical organization have enabled us to create various functional nanomaterials. We have previously demonstrated that N,N′-disubstituted 4,6-diaminopyrimidin-2(1 H)-one (DAP), a guanine–cytosine hybridized molecule, is a versatile building block for the creation of tapelike supramolecular polymer species in solution. In the current study, DAP was functionalized with azobenzene side chains. 1H NMR, UV/Vis, and dynamic light scattering studies confirmed the presence of nanometer-scale tapelike supramolecular polymers in alkane solvents at micromolar regimes. At higher concentrations (millimolar regimes), the supramolecular polymers hierarchically organized into lamellar superstructures to form organogels, as shown by X-ray diffraction and polarized optical microscopy. Remarkably, the azobenzene side chains are photoisomerizable even in the supramolecular polymers, owing to their loosely packed state supported by the rigid hydrogen-bonded scaffold, enabling us to establish photocontrollable supramolecular polymerization and higher order organization of the tapelike supramolecular polymers into lamellar superstructures.
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