Planar π-extended cycloparaphenylenes featuring an all-armchair edge topology

Xiang F, Maisel S, Beniwal S, Akhmetov V, Ruppenstein C, Devarajulu M, Dörr A, Papaianina O, Görling A, Amsharov K, Maier S (2022)

Publication Type: Journal article

Publication year: 2022

Journal

Nature Chemistry Nature Publishing Group

Book Volume: 1^4

Pages Range: 871-876

Journal Issue: 8

DOI: 10.1038/s41557-022-00968-3

Abstract

The [n]cycloparaphenylenes ([n]CPPs)—npara-linked phenylenes that form a closed-loop—have attracted substantial attention due to their unique cyclic structure and highly effective para-conjugation leading to a myriad of fascinating electronic and optoelectronic properties. However, their strained topology prevents the π-extension of CPPs to convert them either into armchair nanobelts or planarized CPP macrocycles. Here we successfully tackle this long-standing challenge and present the bottom-up synthesis and characterization of atomically precise in-plane π-extended [12]CPP on Au(111) by low-temperature scanning probe microscopy and spectroscopy combined with density functional theory. The planar π-extended CPP is a nanographene with an all-armchair edge topology. The exclusive para-conjugation at the periphery yields delocalized electronic states and the planarization maximizes the overlap of p orbitals, which both reduce the bandgap compared to conventional CPPs. Calculations predict ring currents and global aromaticity in the doubly charged system. The intriguing planar ring topology and unique electronic properties make planar π-extended CPPs promising quantum materials. [Figure not available: see fulltext.]

Authors with CRIS profile

Feifei Xiang Lehrstuhl für Festkörperphysik Sven Maisel Lehrstuhl für Theoretische Chemie Sumit Beniwal Sonderforschungsbereich 953/3 Synthetische Kohlenstoffallotrope Vladimir Akhmetov Lehrstuhl für Organische Chemie II Mirunalini Devarajulu Professur für Experimentalphysik (Rastersondenmikroskopie) Andreas Dörr Professur für Experimentalphysik (Rastersondenmikroskopie) Olena Papaianina Lehrstuhl für Organische Chemie II Andreas Görling Lehrstuhl für Theoretische Chemie Konstantin Amsharov Lehrstuhl für Organische Chemie II Sabine Maier Professur für Experimentalphysik (Rastersondenmikroskopie)

Additional Organisation(s)

Graduiertenkolleg 1896/2 In situ Mikroskopie mit Elektronen, Röntgenstrahlen und Rastersonden

Involved external institutions

Martin-Luther-Universität Halle-Wittenberg (MLU) DE Germany (DE)

How to cite

APA:

Xiang, F., Maisel, S., Beniwal, S., Akhmetov, V., Ruppenstein, C., Devarajulu, M.,... Maier, S. (2022). Planar π-extended cycloparaphenylenes featuring an all-armchair edge topology. Nature Chemistry, 1^4(8), 871-876. https://dx.doi.org/10.1038/s41557-022-00968-3

MLA:

Xiang, Feifei, et al. "Planar π-extended cycloparaphenylenes featuring an all-armchair edge topology." Nature Chemistry 1^4.8 (2022): 871-876.

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