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Diindeno-fusion of an anthracene as a design strategy for stable organic biradicals
Univ Oregon, Dept Chem & Biochem, Eugene, OR 97403 USA.;Univ Oregon, Inst Mat Sci, Eugene, OR 97403 USA..
Univ Malaga, Dept Phys Chem, Campus Teatinos S-N, Malaga 229071, Spain..
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
Osaka Univ, Grad Sch Engn Sci, Dept Mat Engn Sci, Toyonaka, Osaka 5608531, Japan..
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2016 (English)In: Nature Chemistry, ISSN 1755-4330, E-ISSN 1755-4349, Vol. 8, no 8, 753-759 p.Article in journal (Refereed) Published
Abstract [en]

The consequence of unpaired electrons in organic molecules has fascinated and confounded chemists for over a century. The study of open-shell molecules has been rekindled in recent years as new synthetic methods, improved spectroscopic techniques and powerful computational tools have been brought to bear on this field. Nonetheless, it is the intrinsic instability of the biradical species that limits the practicality of this research. Here we report the synthesis and characterization of a molecule based on the diindeno[b,i]anthracene framework that exhibits pronounced open-shell character yet possesses remarkable stability. The synthetic route is rapid, efficient and possible on the gram scale. The molecular structure was confirmed through single-crystal X-ray diffraction. From variable-temperature Raman spectroscopy and magnetic susceptibility measurements a thermally accessible triplet excited state was found. Organic field-effect transistor device data show an ambipolar performance with balanced electron and hole mobilities. Our results demonstrate the rational design and synthesis of an air-and temperature-stable biradical compound.

Place, publisher, year, edition, pages
2016. Vol. 8, no 8, 753-759 p.
National Category
Chemical Sciences
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URN: urn:nbn:se:uu:diva-302691DOI: 10.1038/nchem.2518ISI: 000380743300008PubMedID: 27442280OAI: oai:DiVA.org:uu-302691DiVA: diva2:970660
Funder
Swedish Research Council, 621-2011-4177National Supercomputer Centre (NSC), Sweden
Available from: 2016-09-14 Created: 2016-09-08 Last updated: 2016-09-14Bibliographically approved

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Jorner, KjellOttosson, Henrik
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