Synthesis of a quinoidal dithieno[2,3-d;2′,3′-d]benzo[2,1-b;3,4-b′]-dithiophene based open-shell singlet biradicaloid

Debin Xia; Ashok Keerthi; Cunbin An; Martin Baumgarten

doi:10.1039/C6QO00543H

Synthesis of a quinoidal dithieno[2,3-d;2′,3′-d]benzo[2,1-b;3,4-b′]-dithiophene based open-shell singlet biradicaloid†

Debin Xia,‡^ab Ashok Keerthi,‡^bc Cunbin An^b and Martin Baumgarten*^b

* Corresponding authors

^a MIIT Key Laboratory of Critical Materials Technology for New Energy Conversion and Storage, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, 150001 Harbin, P. R. China

^b Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
E-mail: martin.baumgarten@mpip-mainz.mpg.de

^c School of Physics and Astronomy Condensed Matter Physics Group, the University of Manchester, M13 9PL Manchester, UK

Abstract

A fused heteroacene derivative, bis(dicyanomethylene)-end-capped-dithieno[2,3-d;2′,3′-d]benzo[2,1-b;3,4-b′]-dithiophene (4CN-DTmBDT) was synthesized. Its open-shell biradical character in the ground state is studied by a combination of electron paramagnetic resonance (EPR) and nuclear magnetic resonance (NMR). Structural assignment was verified with single crystal X-ray diffraction analysis. A highly stable biradicaloid with a low energy gap and low LUMO level is achieved.

This article is part of the themed collection: Novel π-electron molecular scaffolds

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DOI: https://doi.org/10.1039/C6QO00543H
Article type: Research Article
Submitted: 14 Sep 2016
Accepted: 28 Oct 2016
First published: 31 Oct 2016
This article is Open Access

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Org. Chem. Front., 2017,4, 18-21

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Synthesis of a quinoidal dithieno[2,3-d;2′,3′-d]benzo[2,1-b;3,4-b′]-dithiophene based open-shell singlet biradicaloid

D. Xia, A. Keerthi, C. An and M. Baumgarten, Org. Chem. Front., 2017, 4, 18 DOI: 10.1039/C6QO00543H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Organic Chemistry Frontiers

Synthesis of a quinoidal dithieno[2,3-d;2′,3′-d]benzo[2,1-b;3,4-b′]-dithiophene based open-shell singlet biradicaloid†

Abstract

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Synthesis of a quinoidal dithieno[2,3-d;2′,3′-d]benzo[2,1-b;3,4-b′]-dithiophene based open-shell singlet biradicaloid

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