Self-assembly constructed by perylene bisimide derivatives bearing complementary hydrogen-bonding moieties

An intermediate compound 2, 4-bis(laurylamino)-6-(1-(2-aminoethyl)-piperazine)-1, 3, 5-triazine was prepared by stepwise nucleophilic substitution on triazine ring by lauryl amine and subsequently 1-(2-aminoethyl)-piperazine. Then imidization of perylene-3, 4, 9, 10-tetracarboxylic acid dianhydride with 2,4-bis( laurylamino)-6-(1-(2-aminoethyl)-piperazine)-1, 3, 5-triazine was carried out to afford a novel perylene derivative bearing two melamine blocks (S-2) and 1, 6, 7, 12-tetra(4-tert-butyl phenoxy)-perylene-3, 4, 9, 10-tetracarboxylic acid bisimide (S-1). The hydrogen-bonding interactions between S1 and S2 were investigated by H-1 NMR spectrum, UV/Vis spectrum and fluorescence spectrum. The influences on the morphologies of S-1.S-2 aggregates were investigated. The results show that well-defined nanofibers with a diameter of about 100 nm can be obtained by self-assembly between S-1 and S-2 only in CH2Cl2 solution. Based on these results, guidelines for the molecular design and self-assembly of supramolecular polymer materials are presented.