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, Ashok Keerthi, Cunbin An, Martin Baumgarten^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	18-21
Number of pages	4
Journal	Organic Chemistry Frontiers
Volume	4
Issue number	1
Early online date	31 Oct 2016
DOIs	https://doi.org/10.1039/c6qo00543h
Publication status	Published - 1 Jan 2017

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10.1039/c6qo00543hLicence: CC BY

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title = "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 = "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.",

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year = "2017",

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doi = "10.1039/c6qo00543h",

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T1 - Synthesis of a quinoidal dithieno[2,3-D;2′,3′- d] benzo[2,1- b;3,4- b ′]-dithiophene based open-shell singlet biradicaloid

AU - Xia, Debin

AU - Keerthi, Ashok

AU - An, Cunbin

AU - Baumgarten, Martin

PY - 2017/1/1

Y1 - 2017/1/1

N2 - 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.

AB - 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.

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DO - 10.1039/c6qo00543h

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VL - 4

SP - 18

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JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 1

ER -

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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CCDC 1414138: Experimental Crystal Structure Determination

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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

Abstract

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CCDC 1414138: Experimental Crystal Structure Determination

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