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    Inverse electron-demand diels-alder reactions of tetrazine and norbornene at the air-water interface

    Year: 2022

    Journal: Colloid Surf. B-Biointerfaces, Volume 211, MAR

    Authors: Nakahara, Hiromichi; Hagimori, Masayori; Kannaka, Kento; Mukai, Takahiro; Shibata, Osamu

    Organizations: Japan Society for the Promotion of Science (JSPS) [19K07036]; Grants-in-Aid for Scientific Research [19K07036] Funding Source: KAKEN

    Keywords: Tetrazine; Norbornene; Diels-reaction; Surface pressure; Surface potential; Surface chemistry

    The surface chemistry of the inverse electron-demand Diels-Alder (IEDDA) reaction at the air-water interface is elucidated. Tetrazine (C18-Tz) and norbornene derivatives (C16-NCA) were used as the reactants. Langmuir monolayers of C18-Tz, C16-NCA, and their binary mixtures were prepared on aqueous substrates. The surface properties were analyzed using the surface pressure (pi)-molecular area (A) and surface potential (Delta V)-A isotherms, as well as fluorescence microscopy to monitor the progress of the reaction. First, to provide comparison data to evaluate the reaction on the surface, the two components were mixed in stock solutions of organic solvents for the IEDDA reaction. The Langmuir monolayer spread from the reaction solution was characterized as a function of the reaction time. In the subsequent experiments, the Langmuir monolayers were deposited onto the surface of the substrate solutions by spreading from separate stock solutions of C18-Tz and C16-NCA. The variation of the surface behavior of the monolayers with the molecular area, surface composition of the two components, compression speed of the monolayers, and the temperature was studied. We discuss the effects of the air phase in the reaction field on the reaction efficiency by comparing the results obtained from the two methods.
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