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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.

Author information

1
Department of Physical Chemistry, University of Málaga, 29071, Málaga, Spain.
2
Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
3
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.
4
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.
5
Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
6
Present address: Department of Chemistry, Faculty of Science, Kanagawa University, Kanagawa, 259-1293, Japan.

Abstract

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.

KEYWORDS:

absorption; charge transfer; oligomerization; radicals; structure determination

PMID:
28140501
DOI:
10.1002/anie.201610921

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