Gastrodin‐Modified s ‐Tetrazines for Organized Molecular Films: Effects of Alkyl Chain Structure

ABSTRACT

Three Gastrodin derivatives, each containing a fluorescent s ‐tetrazine moiety and alkyl chains with different lengths and branching structures, were newly synthesized to clarify how alkyl chain structure governs the formation of organized molecular films. s ‐Tetrazine derivatives possess the intriguing characteristic that their luminescence behavior changes sensitively in response to molecular packing; structural transitions may potentially reveal novel luminescent properties. Each derivative formed a stable monolayer on the water surface and exhibited systematic behavioral changes depending on the hydrophobic chain length and the presence or absence of branching. Although no significant differences were observed in the mesoscopic morphologies formed within monolayers, the variations in behavior on the water surface led to differences in the orderliness of the layer structures within the multilayers. Furthermore, the absorption and fluorescence behaviors of the two‐dimensional molecular films differed from those of the corresponding three‐dimensional solids. This result indicates that chemical structure and packing of alkyl chains play a key role in controlling molecular packing and photophysical behavior in organized films.