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In order to assemble amphiphilic adenine having azobenzene, C12AzoC5Ade (AzoAde), at the air–water interface based on the molecular recognition of DNA, we prepared aqueous linear oligothymidylic acids, dTn (n = 4, 6, 8, 10, 30), subphase as templates. Surface pressure–area (−A) isotherms and UV-Vis reflection absorption spectra of AzoAde were measured to investigate the effect of chain length of the oligothymidylic acid on the molecular recognition by forming a complementary A-T base pair. It was showed that AzoAde did not form a stable monolayer on the dT4 subphase and remained monomeric state. While AzoAde provided expanded monolayers and formed J-aggregates of azobenzene moieties on the dTn (n > 4) subphases even at the low molecular density. We also investigated the molecular recognition of template oligonucleotides by comparing dT30 with dA30, indicating that AzoAde had not a specific interaction with dA30 at the air–water interface due to base mismatching. The AzoAde monolayer on the dA30 subphase gave H-aggregate from monomeric state by compressing it. On the other hand, it remained J-aggregated state on dT30 subphase regardless of compression. It was, therefore, suggested that the linear oligothymidylic acids, dTn (n > 4), acted as templates for assembling AzoAde at the air–water interface.
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