Synthesis and Photophysical Properties of Soluble N-Doped Rubicenes via Ruthenium-Catalyzed Transfer Hydrogenative Benzannulation

William G Shuler; Sai P Parvathaneni; Jacob B Rodriguez; Taylor N Lewis; Adam J Berges; Christopher J Bardeen; Michael J Krische

doi:10.1002/chem.202100134

Synthesis and Photophysical Properties of Soluble N-Doped Rubicenes via Ruthenium-Catalyzed Transfer Hydrogenative Benzannulation

Chemistry. 2021 Mar 12;27(15):4898-4902. doi: 10.1002/chem.202100134. Epub 2021 Feb 12.

Authors

William G Shuler¹, Sai P Parvathaneni¹, Jacob B Rodriguez², Taylor N Lewis³, Adam J Berges³, Christopher J Bardeen^{2

3}, Michael J Krische¹

Affiliations

¹ Department of Chemistry, University of Texas at Austin, 105 E 24th St. (A5300), Austin, TX, 78712-1167, USA.
² Department of Materials Science and Engineering, University of California, 501 Big Springs Road, Riverside, CA, 92521, USA.
³ Department of Chemistry, University of California, 501 Big Springs Road, Riverside, CA, 92521, USA.

PMID: 33576516
DOI: 10.1002/chem.202100134

Abstract

Ruthenium-catalyzed butadiene-mediated benzannulation enabled the first synthesis of 3,10-(di-tert-butyl)rubicene and its N-doped derivatives as well as preliminary studies on their photophysical properties. Unlike the parent rubicene and 3,10-(di-tert-butyl)rubicene, which adopt classical herringbone-type packing motifs in the solid state, the N-doped congener 7 b displayed columnar packing with an alternating co-facial arrangement of aromatic and heteroaromatic substructures.

Keywords: PAH compounds; benzannulation; cycloaddition; hydrogen transfer; ruthenium.

Abstract

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