Dresden 2017 – scientific programme
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O: Fachverband Oberflächenphysik
O 51: Nanostructures at Surfaces: 1D and 2D Structures and Networks
O 51.17: Poster
Tuesday, March 21, 2017, 18:30–20:30, P1C
On-surface domino reactions: Glaser coupling and dehydrogenative coupling of a biscarboxylic acid to form polymeric bisacylperoxides — •lacheng liu1,2, hong-ying gao1,2, philipp held3, armido studer3, and harald fuchs1,2 — 1Center for Nanotechnology, Heisenbergstraße 11, 48149 Münster, Germany — 2Physikalisches Institut, Westfälische Wilhelms-Universität, Wilhelm-Klemm-Straße 10, 48149 Münster, Germany — 3Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstraße 40, 48149 Münster, Germany
In this work, we report the on-surface oxidative homocoupling of 6,6'-(1,4-buta-1,3-diynyl)bis(2-naphthoic acid)(BDNA) via bisacylperoxide formation on Au(111) and Au(100) surfaces. By using the dehydrogenative polymerization of the biscarboxylic acid, linear poly-BDNA with a chain length of over 100 nm was observed by scanning tunneling microscopy (STM). It is revealed that the monomer of BDNA can be prepared via on-surface Glaser coupling of 6-ethynyl-2-naphthoic acid (ENA). What's more, to further confirm the existence of the bisacylperoxide linkage, some reference compounds such as bis(2-naphthoyl)peroxide(BNP) were studied by STM and XPS. Under the Glaser coupling conditions, the BDNA directly forming the polymeric peroxide (poly-BDNA) represents a first example of an on-surface domino reaction. The results show that the reaction outcome varies as a function of surface topography and the coverage, to form branched polymers, linear polymers, or 2D metal-organic networks.