Scalable synthesis of 5,11-diethynylated indeno[1,2-b]fluorene-6,12-diones and exploration of their solid state packing

Bradley D Rose; Peter J Santa Maria; Aaron G Fix; Chris L Vonnegut; Lev N Zakharov; Sean R Parkin; Michael M Haley

doi:10.3762/bjoc.10.219

Scalable synthesis of 5,11-diethynylated indeno[1,2-b]fluorene-6,12-diones and exploration of their solid state packing

Beilstein J Org Chem. 2014 Sep 5:10:2122-30. doi: 10.3762/bjoc.10.219. eCollection 2014.

Authors

Bradley D Rose¹, Peter J Santa Maria¹, Aaron G Fix¹, Chris L Vonnegut¹, Lev N Zakharov², Sean R Parkin³, Michael M Haley¹

Affiliations

¹ Department of Chemistry & Biochemistry and the Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, USA.
² CAMCOR, University of Oregon, 1443 East 13th Avenue, Eugene, Oregon 97403, USA.
³ Department of Chemistry, University of Kentucky, Lexington, Kentucky 40506-0055, USA.

Abstract

We report a new synthetic route to 5,11-disubstituted indeno[1,2-b]fluorene-6,12-diones that is amenable to larger scale reactions, allowing for the preparation of gram amounts of material. With this new methodology, we explored the effects on crystal packing morphology for the indeno[1,2-b]fluorene-6,12-diones by varying the substituents on the silylethynyl groups.

Keywords: crystal packing; electron accepting; indenofluorenes; organic electronics; polycyclic conjugated hydrocarbons.