Template-controlled on-surface synthesis of a lanthanide supernaphthalocyanine and its open-chain polycyanine counterpart

Qitang Fan, Jan-Niclas Luy, Martin Liebold, Katharina Greulich, Malte Zugermeier, Jörg Sundermeyer, Ralf Tonner () and J. Michael Gottfried ()
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Qitang Fan: Philipps-Universität Marburg
Jan-Niclas Luy: Philipps-Universität Marburg
Martin Liebold: Philipps-Universität Marburg
Katharina Greulich: Philipps-Universität Marburg
Malte Zugermeier: Philipps-Universität Marburg
Jörg Sundermeyer: Philipps-Universität Marburg
Ralf Tonner: Philipps-Universität Marburg
J. Michael Gottfried: Philipps-Universität Marburg

Nature Communications, 2019, vol. 10, issue 1, 1-8

Abstract: Abstract Phthalocyanines possess unique optical and electronic properties and thus are widely used in (opto)electronic devices, coatings, photodynamic therapy, etc. Extension of their π-electron systems could produce molecular materials with red-shifted absorption for a broader range of applications. However, access to expanded phthalocyanine analogues with more than four isoindoline units is challenging due to the limited synthetic possibilities. Here, we report the controlled on-surface synthesis of a gadolinium-supernaphthalocyanine macrocycle and its open-chain counterpart poly(benzodiiminoisoindoline) on a silver surface from a naphthalene dicarbonitrile precursor. Their formation is controlled by the on-surface high-dilution principle and steered by different metal templates, i.e., gadolinium atoms and the bare silver surface, which also act as oligomerization catalysts. By using scanning tunneling microscopy, photoemission spectroscopy, and density functional theory calculations, the chemical structures along with the mechanical and electronic properties of these phthalocyanine analogues with extended π-conjugation are investigated in detail.

Date: 2019
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DOI: 10.1038/s41467-019-13030-7

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