Supramolecular Spangling, Crocheting, and Knitting of Functionalized Pyrene Molecules on a Silver Surface

T. Kaposi, S.  Joshi, T. Hoh, A. Wiengarten, K. Seufert, M. Paszkiewicz, F.  Klappenberger, D. Ecija, L. Djordjevic, T. Marangoni, D. Bonifazi, J. V. Barth,  W. Auwaerter,
ACS Nano, 2016, 10, 7665–7674
DOI: 10.1021/acsnano.6b02989


Pyrenes, as photoactive polycyclic aromatic hydrocarbons (PAHs), represent promising modules for the bottom-up assembly of functional nanostructures. Here, we introduce the synthesis of a family of pyrene derivatives peripherally functionalized with pyridin-4-ylethynyl termini and comprehensively characterize their self-assembly abilities on a smooth Ag(111) support by scanning tunneling microscopy. By deliberate selection of number and geometric positioning of the pyridyl-terminated substituents, two-dimensional arrays, one-dimensional coordination chains, and chiral, porous kagomé-type networks can be tailored. A comparison to phenyl-functionalized reference pyrenes, not supporting the self-assembly of ordered structures at low coverage, highlights the role of the pyridyl moieties for supramolecular crocheting and knitting. Furthermore, we demonstrate the selective spangling of pores in the two-dimensional pyrene assemblies by a distinct number of iodine atoms as guests by atomically resolved imaging and complementary X-ray photoelectron spectroscopy.

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