Jump to main content
Jump to site search

Issue 11, 2016
Previous Article Next Article

A cross-coupling-annulation cascade from peri-dibromonaphthalimide to pseudo-rylene bisimides

Author affiliations

Abstract

Herein we report a synthetic method to annulate naphthalimide moieties at different positions of a pyrene core by a cascade reaction involving palladium-mediated Suzuki–Miyaura cross-coupling and direct C–H arylation affording a new class of rylene bisimides, which we term as pseudo-rylene bisimides. The Pd-mediated reactions of peri-dibromonaphthalimide and pyrene boronic acid esters lead exclusively to six-membered ring annulation by a cascade C–C bond formation, for which a mechanistic rationale is proposed. Depending on the molecular geometry of the new pseudo-rylene bisimides, their optical properties resemble those of zethrene or terrylene bisimides, or polycyclic aromatic hydrocarbons like coronenes. The structural integrity of this new type of pseudo-rylene bisimides was confirmed by single crystal X-ray analysis.

Graphical abstract: A cross-coupling-annulation cascade from peri-dibromonaphthalimide to pseudo-rylene bisimides

Back to tab navigation

Supplementary files

Publication details

The article was received on 01 Aug 2016, accepted on 06 Sep 2016 and first published on 14 Sep 2016


Article type: Research Article
DOI: 10.1039/C6QO00421K
Author version available: Download Author version (PDF)
Citation: Org. Chem. Front., 2016,3, 1435-1442
  •   Request permissions

    A cross-coupling-annulation cascade from peri-dibromonaphthalimide to pseudo-rylene bisimides

    S. Seifert, D. Schmidt and F. Würthner, Org. Chem. Front., 2016, 3, 1435
    DOI: 10.1039/C6QO00421K

Search articles by author

Spotlight

Advertisements