A new class of fully conjugated indenofluorenes has been synthesized and confirmed by solid-state structure analysis. These indeno[2,1-c]fluorene molecules, containing an antiaromatic as-indacene core (in red), possess high electron affinities and show a broad absorption that reaches into the near-IR region of the electromagnetic spectrum. All of the featured compounds reversibly accept up to two electrons. Their electronic properties make this class of compounds attractive for applications in organic electronic devices.
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Synthesis and optoelectronic properties of indeno[1,2-b]fluorene-6,12-dione donor-acceptor-donor triads.
J Org Chem
November 2014
Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, United States.
We report the synthesis of donor-acceptor-donor triads based on the indeno[1,2-b]fluorene-6,12-dione (IF) scaffold. Arylethynyl donor group attachment expands the light absorption of these molecules to the 600-700 nm region compared to derivatives with nondonating silylethynyl substituents yet does not affect the electron-accepting capabilities of the IF core. All triads show reduction potentials at similar or less negative potentials compared to the silylethynyl derivatives.
View Article and Find Full Text PDFScalable synthesis of 5,11-diethynylated indeno[1,2-b]fluorene-6,12-diones and exploration of their solid state packing.
Beilstein J Org Chem
September 2014
Department of Chemistry & Biochemistry and the Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, USA.
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.
View Article and Find Full Text PDFIndeno[2,1-c]fluorene: a new electron-accepting scaffold for organic electronics.
Org Lett
March 2013
Department of Chemistry & Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, USA.
A new class of fully conjugated indenofluorenes has been synthesized and confirmed by solid-state structure analysis. These indeno[2,1-c]fluorene molecules, containing an antiaromatic as-indacene core (in red), possess high electron affinities and show a broad absorption that reaches into the near-IR region of the electromagnetic spectrum. All of the featured compounds reversibly accept up to two electrons.
View Article and Find Full Text PDFSynthesis, crystal structures, and photophysical properties of electron-accepting diethynylindenofluorenediones.
Org Lett
April 2011
Department of Chemistry & Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, USA.
A series of 6,12-bis[(trialkylsilyl)ethynyl]indeno[1,2-b]fluorene-5,11-diones has been synthesized. X-ray crystallographic analysis of these compounds reveals that triisopropylsilyl (TIPS) substitution on the alkyne terminus affords the largest number of intermolecular π-π interactions in the solid state. Conversely, use of trialkylsilyl groups smaller or larger than TIPS furnishes a variety of crystal-packing motifs that contain fewer π-π interactions.
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