Dresden 2020 – scientific programme

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DS: Fachverband Dünne Schichten

DS 15: Organic Thin Films, Organic-Inorganic Interfaces I (joint session DS/CPP)

DS 15.2: Talk

Tuesday, March 17, 2020, 09:45–10:00, CHE 91

Reestablishing odd-even effects in anthracene-derived monolayers by introduction of a proper symmetry — Christoph Partes¹, Eric Sauter², Michael Gärtner¹, Martin Kind¹, Andika Asyuda², Michael Bolte¹, Andreas Terfort¹, and •Michael Zharnikov² — ¹Institut für Anorganische und Analytische Chemie, Universität Frankfurt, 60438 Frankfurt, Germany — ²Angewandte Physikalische Chemie, Universität Heidelberg, 69120 Heidelberg, Germany

A series of anthracene[2,3-d]oxazolyl-2-alkylthioacetates (AOxCnSAc) with n = 2-6 methylene groups in the alkyl chain were designed and synthesized to investigate the influence of the substitution along the long axis of the molecule on the structural behavior of the respective self-assembled monolayers (SAMs) on Au(111). While in previous work anthracene-terminated alkanethiols, in which the alkyl group was attached to the off-axis 2-position of the acene, showed an exceptionally small influence of the number of methylene groups (n) in the aliphatic linker, the new system exhibits a strong dependence of almost all monolayer properties on the length of the aliphatic linker, with the parity of n being the decisive parameter - so-called odd-even effects. The high quality and well-defined character of these SAMs, along with a low band gap of only 3.0 eV, make them relevant for application in organic and molecular electronics.