5
views
0
recommends
+1 Recommend
0 collections
    0
    shares
      • Record: found
      • Abstract: found
      • Article: not found

      Diindeno-fusion of an anthracene as a design strategy for stable organic biradicals.

      Read this article at

      ScienceOpenPublisherPubMed
      Bookmark
          There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

          Abstract

          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.

          Related collections

          Most cited references 40

          • Record: found
          • Abstract: not found
          • Article: not found

          Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations

            Bookmark
            • Record: found
            • Abstract: not found
            • Article: not found

            Functionalized Pentacene:  Improved Electronic Properties from Control of Solid-State Order

              Bookmark
              • Record: found
              • Abstract: not found
              • Article: not found

              Anomalous Paramagnetism of Copper Acetate

                Bookmark

                Author and article information

                Journal
                Nat Chem
                Nature chemistry
                Springer Nature
                1755-4349
                1755-4330
                Aug 2016
                : 8
                : 8
                Affiliations
                [1 ] Department of Chemistry &Biochemistry and the Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, USA.
                [2 ] Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n, 229071 Malaga, Spain.
                [3 ] Department of Chemistry - BMC, Uppsala University, Box 576, Uppsala 751 23, Sweden.
                [4 ] Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan.
                [5 ] Instituto de Ciencia Molecular, Universidad de Valencia, 46980 Paterna, Valencia, Spain.
                [6 ] CAMCOR, University of Oregon, Eugene, Oregon 97403-1433, USA.
                Article
                nchem.2518
                10.1038/nchem.2518
                27442280

                Comments

                Comment on this article