A highly fluorescent PN-heterocycle-fused pyrene derivative with strong self-dimerisation through hydrogen bonding. Issue 1 (2nd January 2020)

• Record Type: Journal Article
• Authors: Bard, Jeremy P.; Mancuso, Jenna L.; Deng, Chun-Lin; Zakharov, Lev N.; Johnson, Darren W.; Haley, Michael M.
• Is Part Of: Supramolecular chemistry. Volume 32:Issue 1(2020)
• Page Start: 49
• Page End: 55
• Publication Date: 2020-01-02
• Subjects: Pyrene -- phosphaquinolinone -- fluorophore -- hydrogen bond dimer; Macromolecules -- Periodicals; Supramolecular chemistry -- Periodicals; 547.005
• DOI: 10.1080/10610278.2019.1687896
• Languages: English
• ISSNs: 1061-0278

Abstract

ABSTRACT: The pyrene moiety has been utilised in a variety of systems that exhibit either 'turn on' or 'turn off' fluorescence in response to specific analytes. Continued development of hydrogen bonding pyrene-containing scaffolds seeks to establish a wider substrate scope and utility of these hosts. Herein, we report one such example in the form of a pyrene-containing phosphaquinolinone. This molecule exhibits both strong dimerisation in the solution state and π–π stacking within the pyrene backbone in the solid state. Further, it shows an enhanced quantum yield (70%) and a large extinction coefficient compared to its parent framework. Graphical abstract: