Room Temperature Synthesis of a Covalent Monolayer Sheet at Air/Water Interface Using a Shape-Persistent Photoreactive Amphiphilic Monomer

The shape-persistent monomer 3 with its three 1,8-diazaanthracene (DAA) units is spread and compressed at the air/water interface and the layer then converted into a 1.5 nm thick covalent monolayer sheet by photoirradiation under ambient conditions. The sheet obtained under these extremely mild conditions is mechanically stable to carry its own weight when spanned over TEM grids. While its molecular structure cannot be given yet with certainty, it is likely to be the result of [4 + 4]-cycloaddition dimerizations between the DAA units of neighboring monomers. Evidence is based on the wavelength of the monomer fluorescence emission, the kinetics of this emission's intensity decay with irradiation time, and the mechanical sheet stability that suggests a surpassing of percolation threshold. Finally, the thermal stability of the sheet is investigated.