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Angew Chem Int Ed Engl. 2017 Mar 6;56(11):2898-2902. doi: 10.1002/anie.201610921. Epub 2017 Jan 31.

Bis(aminoaryl) Carbon-Bridged Oligo(phenylenevinylene)s Expand the Limits of Electronic Couplings.

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Department of Physical Chemistry, University of Málaga, 29071, Málaga, Spain.
Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
Dpto. Física, Ingeniería de Sistemas y Teoría de la Señal, Dpto. Óptica and Dpto de Física Aplicada and Instituto Universitario de Materiales de Alicante, Universidad de Alicante, Alicante, 03080, Spain.
Department of Molecular Nanoscience and Organic Materials, Institut de Ciència de Materials de Barcelona (ICMAB-CSIC) and Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Campus de la UAB, Bellaterra, 08193, Spain.
Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
Present address: Department of Chemistry, Faculty of Science, Kanagawa University, Kanagawa, 259-1293, Japan.


Carbon-bridged bis(aminoaryl) oligo(para-phenylenevinylene)s have been prepared and their optical, electrochemical, and structural properties analyzed. Their radical cations are class III and class II mixed-valence systems, depending on the molecular size, and they show electronic couplings which are among the largest for the self-exchange reaction of purely organic molecules. In their dication states, the antiferromagnetic coupling is progressively tuned with size from quinoidal closed-shell to open-shell biradicals. The data prove that the electronic coupling in the radical cations and the singlet-triplet gap in the dications show similar small attenuation factors, thus allowing charge/spin transfer over rather large distances.


absorption; charge transfer; oligomerization; radicals; structure determination


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