On-surface synthesis is a bottom-up approach to organic materials with long-range periodicity that involves vapor deposition and self-assembly of molecular building blocks on surfaces, typically noble metals, followed by annealing at high temperatures. Typical building blocks are halogenated porphyrins. Elimination reactions between the functional groups, promoted by heat and assisted by the underlying surface, lead to new intra-and inter-molecular C-C bonds. Cl, Br, and I are frequently used, because of their propensity to establish weak intra-and intermolecular interactions, and their predictable reactivity pattern occurring at low annealing temperatures, however, F remains little studied. Having a small size, F functionalizes crowded positions without leading to distortions, and the high directionality of F- H, F- F, and F- π interactions remains little exploited. This work describes the synthesis and properties of Zn(II) tetraphenylporphyrins partially or fully fluorinated in beta-position and on the meso-phenyl rings to study H-F elimination in chemoselective on-surface syntheses and competing H-H and other H-X elimination reactions on silver substrates. The presentation will focus on synthetic aspects and will summarize also on-surface preliminary results.

Synthesis of fluorine-functionalized ZnTPP derivatives: Novel molecular tiles for covalently bonded 2D organic materials

ACS Spring Meeting 2021

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