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On-surface polyarylene synthesis by cycloaromatization of isopropyl substituents

Amogh Kinikar1*, Marco Di Giovannantonio1, José I. Urgel1, Kristjan Eimre1, Zijie Qiu2, Yanwei Gu2, Enquan Jin2, Akimitsu Narita2, Xiao-Ye Wang2, Klaus Müllen2,3, Pascal Ruffieux1, Carlo Antonio Pignedoli1*, Roman Fasel1,4*

1 Empa, Swiss Federal Laboratories for Materials Science and Technology, 8600 Dübendorf (Switzerland)

2 Max Planck Institute for Polymer Research, 55128 Mainz (Germany)

3 Institute of Physical Chemistry, Johannes Gutenberg, Universität Mainz, 55128 Mainz (Germany)

4 Department of Chemistry, Biochemistry and Pharmaceutical Sciences, University of Bern, 3012 Bern (Switzerland)

* Corresponding authors emails: amogh.kinikar@empa.ch, carlo.pignedoli@empa.ch, roman.fasel@empa.ch
DOI10.24435/materialscloud:yy-sc [version v1]

Publication date: Jan 25, 2022

How to cite this record

Amogh Kinikar, Marco Di Giovannantonio, José I. Urgel, Kristjan Eimre, Zijie Qiu, Yanwei Gu, Enquan Jin, Akimitsu Narita, Xiao-Ye Wang, Klaus Müllen, Pascal Ruffieux, Carlo Antonio Pignedoli, Roman Fasel, On-surface polyarylene synthesis by cycloaromatization of isopropyl substituents, Materials Cloud Archive 2022.12 (2022), doi: 10.24435/materialscloud:yy-sc.

Description

In this record we provide the data to support our recent finding on surface catalyzed cycloaromatization. Immobilization of organic building blocks on metal surfaces and their coupling via thermally induced C-C bond formations are developing as an important addition to the toolbox of organic and polymer synthesis. Additional advantages of this technique are the in situ monitoring of the reaction by scanning probe methods and the accessibility of insoluble and reactive carbon nanostructures. The diversity of conceivable products, however, sensitively depends on the number of available on-surface reactions. In the manuscript where the results are discussed, we introduce an unprecedented example, the intermolecular oxidative coupling of isopropyl substituents of arenes. With a new phenylene ring being formed, this [3+3] dimerization can be regarded as a formal cycloaromatization. The synthetic value of this novel reaction is proven by the synthesis of polyarylenes and co-polyarylenes, which we demonstrate by synthesizing poly(2,7-pyrenylene-1,4-phenylene). Scanning tunneling microscopy and non-contact atomic force microscopy studies complemented by density functional theory calculations are employed to obtain mechanistic insights into the title reaction.

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Files and data are licensed under the terms of the following license: Creative Commons Attribution 4.0 International.
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External references

Journal reference (Paper where the data is discussed)
A. Kinikar, M. Di Giovannantonio, J. I. Urgel, K. Eimre, Z. Qiu, Y. Gu, E. Jin, A. Narita, X. Wang, K. Müllen, P. Ruffieux, C. A. Pignedoli, and R. Fasel, Nature Synthesis (2022) doi:10.1038/s44160-022-00032-5

Keywords

Catalysis ab initio on surface synthesis MARVEL/DD3 SNSF

Version history:

2022.12 (version v1) [This version] Jan 25, 2022 DOI10.24435/materialscloud:yy-sc