title: Self-assembly and chemical modifications of bisphenol a on Cu(111): interplay between ordering and thermally activated stepwise deprotonation.
abstract: Bisphenol A (BPA) is a chemical widely used in the synthesis pathway of polycarbonates for the production of many daily used products. Besides other adverse health effects, medical studies have shown that BPA can cause DNA hypomethylation and therefore alters the epigenetic code. In the present work, the reactivity and self-assembly of the molecule was investigated under ultra-high-vacuum conditions on a Cu(111) surface. We show that the surface-confined molecule goes through a series of thermally activated chemical transitions. Scanning tunneling microscopy investigations showed multiple distinct molecular arrangements dependent on the temperature treatment and the formation of polymer-like molecular strings for temperatures above 470 K. X-ray photoelectron spectroscopy measurements revealed the stepwise deprotonation of the hydroxy groups, which allows the molecules to interact strongly with the underlying substrate as well as their neighboring molecules and therefore drive the organization into distinct structural arrangements. On the basis of the combined experimental evidence in conjunction with density functional theory calculations, structural models for the self-assemblies after the thermal treatment were elaborated.
authors.affiliation: Physik Department E20, Technische Universität München , D-85748 Garching, Germany.
authors.forename: Sybille
authors.initials: S
authors.lastname: Fischer
authors.forename: Anthoula C
authors.initials: AC
authors.lastname: Papageorgiou
authors.forename: Julian A
authors.initials: JA
authors.lastname: Lloyd
authors.forename: Seung Cheol
authors.initials: SC
authors.lastname: Oh
authors.forename: Katharina
authors.initials: K
authors.lastname: Diller
authors.forename: Francesco
authors.initials: F
authors.lastname: Allegretti
authors.forename: Florian
authors.initials: F
authors.lastname: Klappenberger
authors.forename: Ari Paavo
authors.initials: AP
authors.lastname: Seitsonen
authors.forename: Joachim
authors.initials: J
authors.lastname: Reichert
authors.forename: Johannes V
authors.initials: JV
authors.lastname: Barth
mesh_terms: D001559:Benzhydryl Compounds / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D016252:Microscopy, Scanning Tunneling; D010636:Phenols / Q000737:chemistry*; D056951:Photoelectron Spectroscopy; D011522:Protons; D000098826:Bisphenol A Compounds
chemical_list: D001559:Benzhydryl Compounds; D003300:Copper; D010636:Phenols; D011522:Protons; C006780:bisphenol A; D000098826:Bisphenol A Compounds