Construction of biphenylene dimers and surface-bound layers to explore donor-acceptor interactions

Abstract Molecular complexes based on donor-acceptor interactions that involve π-systems with antiaromatic character are rarely studied. Herein, we report the synthesis of biphenylene derivatives as potential electron donor components in π-complexes. Molecules with two connected biphenylene units are suitable to probe the formation of differently folded complexes in solution, while biphenylene derivatives with a pendant triethoxysilane group can be used to functionalize solid surfaces and probe interfacial donor-acceptor complex formation. Our results show clear indication of complex formation in solution; however, no observable interaction was found on the surface using UV-vis spectroscopy.