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O: Fachverband Oberflächenphysik

O 87: Focus Session: Molecular Nanostructures on Surfaces: On-Surface Synthesis and Single-Molecule Manipulation III

O 87.3: Talk

Thursday, March 21, 2024, 15:45–16:00, HE 101

The Chemical Functionalization of the Biphenylene Network predicted by DFT — •Hendrik Weiske and Ralf Tonner-Zech — Universität Leipzig, Leipzig, Deutschland

2D materials, such as graphene, could introduce a new disruptive technology, replacing some of the currently used materials. The covalent functionalization of graphene is still relatively uncommon and limited to powerful reagents, e.g., free radicals, n-BuLi, or strong nucleophiles.[1] The biphenylene network (BPN) is a recently synthesized 2D material[2] with a promising application range, from photocatalysis to superconductivity. While hydrogenated or fluorinated derivatives of BPN are discussed in the literature already, the molecular functionalization is an unexplored topic in the field. We show that the unique electronic structure of BPN enables functionalization using the stable unsaturated cyclic hydrocarbon cyclooctyne. Cyclooctyne is known to form well-ordered layers on Si(001), which we studied extensively in the past.[3,4] We propose cyclooctyne as a promising molecule to functionalize BPN towards new properties. We extensively studied the adsorption kinetics of cyclooctyne, thermodynamics, chemoselectivity for the reaction, and its effect on the electronic structure.

[1] I. A. Vacchi, A. Bianco, et al., Phys. Sci. Rev., 2017, 2. [2] Q. Fan, A. S. Foster, U. Koert, P. Liljeroth, J. M. Gottfried, et al., Science 2021, 372, 852-856. [3] F. Pieck, R. Tonner-Zech, Molecules, 2021, 26, 6653 [4] L. Pecher, R. Tonner, et al., J. Phys. Chem. C, 2017, 121, 26840-26850

Keywords: DFT; biphenylene network; cyclooctyne; covalent functionalization; 2D