Synthesis of Oligo(1,8-pyrenylene)s: A Series of Functional Molecular Liquids

Joshua C Walsh; David T Hogan; Kerry-Lynn M Williams; Simon D Brake; Gandikota Venkataramana; Tara A Misener; Brandon J Wallace; Richard P Johnson; David W Thompson; Yuming Zhao; Brian D Wagner; Graham J Bodwell

doi:10.1002/cplu.201900133

Synthesis of Oligo(1,8-pyrenylene)s: A Series of Functional Molecular Liquids

Chempluschem. 2019 Jun;84(6):754-765. doi: 10.1002/cplu.201900133. Epub 2019 May 9.

Affiliations

¹ Chemistry Department, Memorial University of Newfoundland, 283 Prince Philip Drive, St. John's, NL A1B 3X7, Canada.
² Chemistry Department, University of Prince Edward Island, 550 University Ave, Charlottetown, PE C1A 4P3, Canada.
³ Department of Chemistry and Materials Science Program, University of New Hampshire, Durham, NH 03824, USA.

PMID: 31944011
DOI: 10.1002/cplu.201900133

Abstract

A monomer-through-pentamer series of oligo(1,8-pyrenylene)s was synthesized using a two-step iterative synthetic strategy. The trimer, tetramer, and pentamer are mixtures of atropisomers that interconvert slowly at room temperature (as shown by variable-temperature NMR analysis). They are liquids well below room temperature, as indicated by POM, DSC and SWAXS analysis. These oligomers are highly fluorescent both in the liquid state and in dilute solution (λ_F,max = 444-457 nm, φ_F = 0.80) and an investigation of their photophysical properties demonstrated that delocalization plays a larger role in their excited states than it does in related pyrene-based oligomers.

Keywords: atropisomerism; functional molecular liquids; iterative synthesis; oligoarylenes; pyrene.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.