Controlling intermolecular redox-doping of naphthalene diimides

Simon B. Schmidt, Till Biskup, Xuechen Jiao, Christopher R. McNeill, Michael Sommer

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Naphthalene diimide (NDI) with tertiary amine side chains is used to n-dope a series of NDI derivatives of varying energy levels. We demonstrate a photoinduced, intermolecular redox-doping process in which a dimethylpropyl amine side chain attached to one NDI reduces another NDI derivative to form radical anions. The influence of the aromatic core substituents on energy levels, doping efficacy and radical anion stability is studied by cyclic voltammetry, UV-Vis and electron paramagnetic resonance (EPR) spectroscopy. In general, the HOMO energy level of the NDI is responsible for the doping process and the LUMO for air stability of the resulting radical anion. The most electron deficient NDI derivative having two cyano substituents displays the highest doping yield and yields air stable radical anions for both light- and thermally-induced doping. Thermal doping is further accompanied by morphologic changes that stabilize radical anions in air.

Original languageEnglish
Pages (from-to)4466-4474
Number of pages9
JournalJournal of Materials Chemistry C
Volume7
Issue number15
DOIs
Publication statusPublished - 19 Mar 2019

Cite this

Schmidt, Simon B. ; Biskup, Till ; Jiao, Xuechen ; McNeill, Christopher R. ; Sommer, Michael. / Controlling intermolecular redox-doping of naphthalene diimides. In: Journal of Materials Chemistry C. 2019 ; Vol. 7, No. 15. pp. 4466-4474.
@article{4f1f5dcbce2e4d93a7cecdea28dfcc20,
title = "Controlling intermolecular redox-doping of naphthalene diimides",
abstract = "Naphthalene diimide (NDI) with tertiary amine side chains is used to n-dope a series of NDI derivatives of varying energy levels. We demonstrate a photoinduced, intermolecular redox-doping process in which a dimethylpropyl amine side chain attached to one NDI reduces another NDI derivative to form radical anions. The influence of the aromatic core substituents on energy levels, doping efficacy and radical anion stability is studied by cyclic voltammetry, UV-Vis and electron paramagnetic resonance (EPR) spectroscopy. In general, the HOMO energy level of the NDI is responsible for the doping process and the LUMO for air stability of the resulting radical anion. The most electron deficient NDI derivative having two cyano substituents displays the highest doping yield and yields air stable radical anions for both light- and thermally-induced doping. Thermal doping is further accompanied by morphologic changes that stabilize radical anions in air.",
author = "Schmidt, {Simon B.} and Till Biskup and Xuechen Jiao and McNeill, {Christopher R.} and Michael Sommer",
year = "2019",
month = "3",
day = "19",
doi = "10.1039/c9tc00721k",
language = "English",
volume = "7",
pages = "4466--4474",
journal = "Journal of Materials Chemistry C",
issn = "2050-7526",
publisher = "The Royal Society of Chemistry",
number = "15",

}

Controlling intermolecular redox-doping of naphthalene diimides. / Schmidt, Simon B.; Biskup, Till; Jiao, Xuechen; McNeill, Christopher R.; Sommer, Michael.

In: Journal of Materials Chemistry C, Vol. 7, No. 15, 19.03.2019, p. 4466-4474.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Controlling intermolecular redox-doping of naphthalene diimides

AU - Schmidt, Simon B.

AU - Biskup, Till

AU - Jiao, Xuechen

AU - McNeill, Christopher R.

AU - Sommer, Michael

PY - 2019/3/19

Y1 - 2019/3/19

N2 - Naphthalene diimide (NDI) with tertiary amine side chains is used to n-dope a series of NDI derivatives of varying energy levels. We demonstrate a photoinduced, intermolecular redox-doping process in which a dimethylpropyl amine side chain attached to one NDI reduces another NDI derivative to form radical anions. The influence of the aromatic core substituents on energy levels, doping efficacy and radical anion stability is studied by cyclic voltammetry, UV-Vis and electron paramagnetic resonance (EPR) spectroscopy. In general, the HOMO energy level of the NDI is responsible for the doping process and the LUMO for air stability of the resulting radical anion. The most electron deficient NDI derivative having two cyano substituents displays the highest doping yield and yields air stable radical anions for both light- and thermally-induced doping. Thermal doping is further accompanied by morphologic changes that stabilize radical anions in air.

AB - Naphthalene diimide (NDI) with tertiary amine side chains is used to n-dope a series of NDI derivatives of varying energy levels. We demonstrate a photoinduced, intermolecular redox-doping process in which a dimethylpropyl amine side chain attached to one NDI reduces another NDI derivative to form radical anions. The influence of the aromatic core substituents on energy levels, doping efficacy and radical anion stability is studied by cyclic voltammetry, UV-Vis and electron paramagnetic resonance (EPR) spectroscopy. In general, the HOMO energy level of the NDI is responsible for the doping process and the LUMO for air stability of the resulting radical anion. The most electron deficient NDI derivative having two cyano substituents displays the highest doping yield and yields air stable radical anions for both light- and thermally-induced doping. Thermal doping is further accompanied by morphologic changes that stabilize radical anions in air.

UR - http://www.scopus.com/inward/record.url?scp=85064272340&partnerID=8YFLogxK

U2 - 10.1039/c9tc00721k

DO - 10.1039/c9tc00721k

M3 - Article

VL - 7

SP - 4466

EP - 4474

JO - Journal of Materials Chemistry C

JF - Journal of Materials Chemistry C

SN - 2050-7526

IS - 15

ER -