Repurposing DNA-binding agents as H-bonded organic semiconductors

Fengjiao Zhang, Vincent Lemaur, Wookjin Choi, Prapti Kafle, Shu Seki, Jérôme Cornil, David Beljonne and Ying Diao ()
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Fengjiao Zhang: University of Illinois at Urbana−Champaign
Vincent Lemaur: University of Mons
Wookjin Choi: Kyoto University
Prapti Kafle: University of Illinois at Urbana−Champaign
Shu Seki: Kyoto University
Jérôme Cornil: University of Mons
David Beljonne: University of Mons
Ying Diao: University of Illinois at Urbana−Champaign

Nature Communications, 2019, vol. 10, issue 1, 1-11

Abstract: Abstract Organic semiconductors are usually polycyclic aromatic hydrocarbons and their analogs containing heteroatom substitution. Bioinspired materials chemistry of organic electronics promises new charge transport mechanism and specific molecular recognition with biomolecules. We discover organic semiconductors from deoxyribonucleic acid topoisomerase inhibitors, featuring conjugated backbone decorated with hydrogen-bonding moieties distinct from common organic semiconductors. Using ellipticine as a model compound, we find that hydrogen bonds not only guide polymorph assembly, but are also critical to forming efficient charge transport pathways along π−conjugated planes when at a low dihedral angle by shortening the end-to-end distance of adjacent π planes. In the π−π stacking and hydrogen-bonding directions, the intrinsic, short-range hole mobilities reach as high as 6.5 cm2V−1s−1 and 4.2 cm2V−1s−1 measured by microwave conductivity, and the long-range apparent hole mobilities are up to 1.3 × 10–3 cm2V−1s−1 and 0.4 × 10–3 cm2V−1s−1 measured in field-effect transistors. We further demonstrate printed transistor devices and chemical sensors as potential applications.

Date: 2019
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DOI: 10.1038/s41467-019-12248-9

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