Self-assembly of a new series of quadruply hydrogen bonded heterotrimers driven by the donor–acceptor interaction

This paper describes the self-assembly of a new series of heterotrimers in chloroform-d by utilizing the cooperative interaction of hydrogen bonding and donor–acceptor interaction. Compounds and , in which an 2-ureido-4[1H]-pyrimidinone unit is connected to 34-crown-10 or 36-crown-10, were used as donor monomer, and and , in which an 2-ureido-4[1H]-pyrimidinone unit is connected to NDI, were used as acceptor monomer, while linear compound , which contains two diamido-1,8-naphthyridines, was used as template. A large tri-p-(t-butyl)phenylmethoxyl group was introduced to in order to compare its assembling behavior with that of . Mixing with dimer caused to fully decompose and to afford 55% of ‘in–in’-oriented heterotrimer . Adding to the solution of or in chloroform-d also led to full dissociation of the dimers. However, in these systems the ‘in–in’-arranged heterotrimer or could be produced exclusively.