Repurposing DNA-binding agents as H-bonded organic semiconductors

Fengjiao Zhang, Vincent Lemaur, Wookjin Choi, Prapti Kafle, Shu Seki, Jérôme Cornil, David Beljonne, Ying Diao

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Article number4217
JournalNature communications
Volume10
Issue number1
DOIs
StatePublished - Dec 1 2019

Fingerprint

Semiconductors
Semiconducting organic compounds
organic semiconductors
Hydrogen bonds
Hole mobility
deoxyribonucleic acid
ellipticine
hole mobility
Hydrogen Bonding
Charge transfer
DNA
Topoisomerase Inhibitors
Organic Chemistry
Molecular recognition
Polycyclic Aromatic Hydrocarbons
Biomolecules
polycyclic aromatic hydrocarbons
Dihedral angle
hydrogen
Microwaves

ASJC Scopus subject areas

  • Chemistry(all)
  • Biochemistry, Genetics and Molecular Biology(all)
  • Physics and Astronomy(all)

Cite this

Repurposing DNA-binding agents as H-bonded organic semiconductors. / Zhang, Fengjiao; Lemaur, Vincent; Choi, Wookjin; Kafle, Prapti; Seki, Shu; Cornil, Jérôme; Beljonne, David; Diao, Ying.

In: Nature communications, Vol. 10, No. 1, 4217, 01.12.2019.

Research output: Contribution to journalArticle

Zhang, F, Lemaur, V, Choi, W, Kafle, P, Seki, S, Cornil, J, Beljonne, D & Diao, Y 2019, 'Repurposing DNA-binding agents as H-bonded organic semiconductors', Nature communications, vol. 10, no. 1, 4217. https://doi.org/10.1038/s41467-019-12248-9
Zhang F, Lemaur V, Choi W, Kafle P, Seki S, Cornil J et al. Repurposing DNA-binding agents as H-bonded organic semiconductors. Nature communications. 2019 Dec 1;10(1). 4217. https://doi.org/10.1038/s41467-019-12248-9
Zhang, Fengjiao ; Lemaur, Vincent ; Choi, Wookjin ; Kafle, Prapti ; Seki, Shu ; Cornil, Jérôme ; Beljonne, David ; Diao, Ying. / Repurposing DNA-binding agents as H-bonded organic semiconductors. In: Nature communications. 2019 ; Vol. 10, No. 1.
@article{ba203c8459864b31bb72ad671662f597,
title = "Repurposing DNA-binding agents as H-bonded organic semiconductors",
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.",
author = "Fengjiao Zhang and Vincent Lemaur and Wookjin Choi and Prapti Kafle and Shu Seki and J{\'e}r{\^o}me Cornil and David Beljonne and Ying Diao",
year = "2019",
month = "12",
day = "1",
doi = "10.1038/s41467-019-12248-9",
language = "English (US)",
volume = "10",
journal = "Nature Communications",
issn = "2041-1723",
publisher = "Nature Publishing Group",
number = "1",

}

TY - JOUR

T1 - Repurposing DNA-binding agents as H-bonded organic semiconductors

AU - Zhang, Fengjiao

AU - Lemaur, Vincent

AU - Choi, Wookjin

AU - Kafle, Prapti

AU - Seki, Shu

AU - Cornil, Jérôme

AU - Beljonne, David

AU - Diao, Ying

PY - 2019/12/1

Y1 - 2019/12/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85072269238&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85072269238&partnerID=8YFLogxK

U2 - 10.1038/s41467-019-12248-9

DO - 10.1038/s41467-019-12248-9

M3 - Article

C2 - 31527590

AN - SCOPUS:85072269238

VL - 10

JO - Nature Communications

JF - Nature Communications

SN - 2041-1723

IS - 1

M1 - 4217

ER -