The synthesis of 1,18-nucleotide-appended bolaamphiphiles (1, 2, 4, and 6) is reported, in which a 3′-phosphorylated guanidine, adenosine, thymidine, or cytidine is connected to each end of an octadecamethylene chain. Single-component self-assemblies and binary self-assemblies with the complementary oligonucleotides dC20, dT20, dA20, and dG20 are studied by atomic force microscopy, powder X-ray diffraction analysis, temperature-dependent UV absorption, circular dichroism, and attenuated total-reflection Fourier-transform infrared spectroscopy. The single-component self-assembly of 1 forms a two-dimensional sheet, whereas the binary self-assembly 1/dC20 gives helical nanofibers. Non-helical nanofibers are observed for the single-component self-assemblies of 2 and 4, and helical nanofibers form from the binary self-assembly 2/dT20. Interestingly, helical nanorod structures are obtained from the binary self-assembly 4/dA20, and the aligned nanorods form a nematic phase. The single-component and binary self-assemblies from 6 give unilamellar vesicles owing to a lack of stacking interaction between the cytosine moieties.
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