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On-Surface Pseudo-High-Dilution Synthesis of Macrocycles: Principle and Mechanism

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† National Synchrotron Radiation Laboratory and Collaborative Innovation Center of Suzhou Nano Science and Technology, University of Science and Technology of China, Hefei 230029, P.R. China
‡ Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Str., 35032 Marburg, Germany
*E-mail: [email protected]
*E-mail: [email protected]
Cite this: ACS Nano 2017, 11, 5, 5070–5079
Publication Date (Web):April 18, 2017
https://doi.org/10.1021/acsnano.7b01870
Copyright © 2017 American Chemical Society
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    Abstract

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    Macrocycles have attracted much attention due to their specific “endless” topology, which results in extraordinary properties compared to related linear (open-chain) molecules. However, challenges still remain in their controlled synthesis with well-defined constitution and geometry. Here, we report the successful application of the (pseudo-)high-dilution method to the conditions of on-surface synthesis in ultrahigh vacuum. This approach leads to high yields (up to 84%) of cyclic hyperbenzene ([18]-honeycombene) via an Ullmann-type reaction from 4,4″-dibromo-meta-terphenyl (DMTP) as precursor on a Ag(111) surface. The mechanism of macrocycle formation was explored in detail using scanning tunneling microscopy and X-ray photoemission spectroscopy. We propose that the dominant pathway for hyperbenzene (MTP)6 formation is the stepwise desilverization of an organometallic (MTP-Ag)6 macrocycle, which forms via cyclization of (MTP-Ag)6 chains under pseudo-high-dilution conditions. The high probability of cyclization on the stage of the organometallic phase results from the reversibility of the C–Ag bond. The case is different from that in solution, in which cyclization typically occurs on the stage of a covalently bonded open-chain precursor. This difference in the cyclization mechanism on a surface compared to that in solution stems mainly from the 2D confinement exerted by the surface template, which hinders the flipping of chain segments necessary for cyclization.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acsnano.7b01870.

    • Br 3p XP spectra, additional STM images with statistical and geometric analysis, detailed isomerization schemes, derivation of eq 1 and of the stationary DMTP concentration during low-flux deposition (PDF)

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