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Rules of Nucleophilic Additions to Zigzag Nanographene Diones


Ribar, Peter; Valenta, Leos; Solomek, Tomas; Juricek, Michal (2021). Rules of Nucleophilic Additions to Zigzag Nanographene Diones. Angewandte Chemie Internationale Edition, (60):13521-13528.

Abstract

Nucleophilic addition of carbon-centered nucleophiles to nanographene ketones represents a valuable late-stage method for the functionalization of zigzag nanographenes, but its use is rare in the chemical literature. Using two model systems, non-Kekulé triangulene-4,8-dione and Kekulé anthanthrone, we identify unexpected regioselectivities and uncover the rules that govern these reactions. Considering the large number of nanographene ketones that have been reported since the pioneering work of Eric Clar, this method enables synthesis and exploration of hitherto unknown functionalized nanographenes.

Abstract

Nucleophilic addition of carbon-centered nucleophiles to nanographene ketones represents a valuable late-stage method for the functionalization of zigzag nanographenes, but its use is rare in the chemical literature. Using two model systems, non-Kekulé triangulene-4,8-dione and Kekulé anthanthrone, we identify unexpected regioselectivities and uncover the rules that govern these reactions. Considering the large number of nanographene ketones that have been reported since the pioneering work of Eric Clar, this method enables synthesis and exploration of hitherto unknown functionalized nanographenes.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Catalysis
Physical Sciences > General Chemistry
Language:English
Date:7 June 2021
Deposited On:15 Feb 2022 14:12
Last Modified:22 Mar 2024 04:34
Publisher:Wiley-VCH Verlag
ISSN:1433-7851
OA Status:Green
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.26434/chemrxiv.13348049.v1
Project Information:
  • : FunderSNSF
  • : Grant IDPZ00P2_174175
  • : Project TitleThree-Dimensional Molecular Electron Acceptors for Efficient Electron-Transporting Materials
  • : FunderH2020
  • : Grant ID716139
  • : Project TitleSpin-Delocalization with a Twist: Chiral Open-Shell Helices
  • Content: Published Version
  • Language: English
  • Licence: Creative Commons: Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)