title: On-Surface Domino Reactions: Glaser Coupling and Dehydrogenative Coupling of a Biscarboxylic Acid To Form Polymeric Bisacylperoxides.
abstract: Herein 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 different Au substrates. By using this unprecedented dehydrogenative polymerization of a biscarboxylic acid, linear poly-BDNA with a chain length of over 100 nm was prepared. It is shown that the monomer BDNA can be prepared in situ at the surface via on-surface Glaser coupling of 6-ethynyl-2-naphthoic acid (ENA). Under the Glaser coupling conditions, BDNA directly undergoes polymerization to give the polymeric peroxide (poly-BDNA) representing a first example of an on-surface domino reaction. It is shown that the reaction outcome varies as a function of surface topography (Au(111) or Au(100)) and also of the surface coverage, to give branched polymers, linear polymers, or 2D metal-organic networks.
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149, Münster, Germany.
authors.forename: Philipp Alexander
authors.initials: PA
authors.lastname: Held
authors.affiliation: Physikalisches Institut, Westfälische Wilhelms-Universität Münster, Wilhelm-Klemm-Strasse 10, 48149, Münster, Germany. gaoh@uni-muenster.de.|Center for Nanotechnology (CeNTech), Heisenbergstrasse 11, 48149, Münster, Germany. gaoh@uni-muenster.de.
authors.forename: Hong-Ying
authors.initials: HY
authors.lastname: Gao
authors.affiliation: Physikalisches Institut, Westfälische Wilhelms-Universität Münster, Wilhelm-Klemm-Strasse 10, 48149, Münster, Germany.|Center for Nanotechnology (CeNTech), Heisenbergstrasse 11, 48149, Münster, Germany.
authors.forename: Lacheng
authors.initials: L
authors.lastname: Liu
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149, Münster, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Mück-Lichtenfeld
authors.affiliation: Physikalisches Institut, Westfälische Wilhelms-Universität Münster, Wilhelm-Klemm-Strasse 10, 48149, Münster, Germany.|Center for Nanotechnology (CeNTech), Heisenbergstrasse 11, 48149, Münster, Germany.
authors.forename: Alexander
authors.initials: A
authors.lastname: Timmer
authors.affiliation: Physikalisches Institut, Westfälische Wilhelms-Universität Münster, Wilhelm-Klemm-Strasse 10, 48149, Münster, Germany.|Center for Nanotechnology (CeNTech), Heisenbergstrasse 11, 48149, Münster, Germany.
authors.forename: Harry
authors.initials: H
authors.lastname: Mönig
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149, Münster, Germany.
authors.forename: Dennis
authors.initials: D
authors.lastname: Barton
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149, Münster, Germany.
authors.forename: Johannes
authors.initials: J
authors.lastname: Neugebauer
authors.affiliation: Physikalisches Institut, Westfälische Wilhelms-Universität Münster, Wilhelm-Klemm-Strasse 10, 48149, Münster, Germany. fuchsh@uni-muenster.de.|Center for Nanotechnology (CeNTech), Heisenbergstrasse 11, 48149, Münster, Germany. fuchsh@uni-muenster.de.
authors.forename: Harald
authors.initials: H
authors.lastname: Fuchs
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149, Münster, Germany. studer@uni-muenster.de.
authors.forename: Armido
authors.initials: A
authors.lastname: Studer
keywords: Glaser coupling; gold; scanning tunneling microscopy; self-assembly; surface chemistry