Dissymmetrical Chiral Peropyrenes: Synthesis via Iridium-Catalyzed C-H Activation/Alkyne Benzannulation and Study of Their Properties

Stephen P George; Jonas Spengler; Ryan J Malone; James Krzoska; Frank Würthner; Wesley A Chalifoux

doi:10.1021/acs.joc.3c02985

Dissymmetrical Chiral Peropyrenes: Synthesis via Iridium-Catalyzed C-H Activation/Alkyne Benzannulation and Study of Their Properties

J Org Chem. 2024 Apr 5;89(7):5159-5163. doi: 10.1021/acs.joc.3c02985. Epub 2024 Mar 27.

Authors

Stephen P George¹, Jonas Spengler², Ryan J Malone³, James Krzoska³, Frank Würthner², Wesley A Chalifoux³

Affiliations

¹ Department of Chemistry, University of Nevada, Reno, 1664 North Virginia Street, Reno, Nevada 89557, United States.
² Institut für Organische Chemie and Center for Nanosystems Chemistry (CNC), Universität Würzburg, 97074 Würzburg, Germany.
³ Department of Chemistry, University of Alberta, 11227 Saskatchewan Drive, Edmonton, Alberta T6G 2G2, Canada.

PMID: 38532683
DOI: 10.1021/acs.joc.3c02985

Abstract

Dissymmetrical chiral peropyrenes with electron-rich and electron-deficient aryl substituents in the bay regions were synthesized via iridium-catalyzed C-H activation and alkyne benzannulation. The electronic properties were studied using cyclic and differential pulse voltammetry. The enantiomers were separated and exhibited high g_lum and g_abs values in circularly polarized luminescence (CPL) and circular dichroism (CD), respectively. Variable-temperature NMR experiments were conducted on symmetrical and dissymmetrical chiral peropyrenes to compare the barrier to rotation of the aryl groups in the bay region.