Synthesis of self-assembled nucleobases and their anhydrous proton conductivity

We synthesized self-assembled nucleobases (SANs), such as 1-dodecylthymine (DOT) or 9-dodecyladenine (DOA), in which the nucleobase is immobilized on a long alkyl chain. The thermal stability of the SAN was increased by mixing with the acidic surfactant mono-dodecyl phosphate (MDP). Additionally, the SAN–MDP composite material showed proton conductivity of 4.62 × 10⁻⁴ S cm⁻¹ at 160 °C under anhydrous conditions. Additionally, the activation energy of the proton conduction was approximately 0.2 eV and this value was one order of magnitude higher than that of a typical humidified perfluorinated membrane, in which the proton can be moved by vehicle molecules, such as water molecules. In contrast, when the nucleobase without the immobilization of a long alkyl chain was mixed with MDP, the proton conductivity of these composite materials was two orders of magnitude less than that of the SAN–MDP composite. Therefore, we measured the XRD spectra of the SAN–MDP composite material. As a result, the SAN–MDP composite material showed a self-assembled structure with a two-dimensional proton conducting pathway, such as a lamellar structure, and that the anhydrous proton conduction was related to the interaction between the nucleobase of the SAN and the phosphate group of MDP. Consequently, the self-assembled nucleobase derivatives have the potential for use as novel anhydrous proton conductors with a two-dimensional proton conducting pathway.

We synthesized the proton conductive self-assembled nucleobase, such as 1-dodecylthymine and 9-dodecyladenine, in which the nucleobase is immobilized on a long alkyl chain.