Universität zu Köln

Schmidt, Simon B., Hoenig, Markus, Shin, Younghun, Cassinelli, Marco, Perinot, Andrea, Caironi, Mario ORCID: 0000-0002-0442-4439, Jiao, Xuechen ORCID: 0000-0001-7387-0275, McNeill, Christopher R. ORCID: 0000-0001-5221-878X, Fazzi, Daniele ORCID: 0000-0002-8515-4214, Biskup, Till ORCID: 0000-0003-2913-0004 and Sommer, Michael (2020). Radical Anion Yield, Stability, and Electrical Conductivity of Naphthalene Diimide Copolymers n-Doped with Tertiary Amines. ACS Appl. Polym. Mater., 2 (5). S. 1954 - 1964. WASHINGTON: AMER CHEMICAL SOC. ISSN 2637-6105

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Abstract

Doped organic semiconductors are required for applications such as organic solar cells, organic light-emitting diodes, and thermoelectric generators. To further establish structure-property relationships and improve the efficiency of these devices, electron-acceptor conjugated polymers and suitable doping schemes are required. A key criterion is a sufficiently low lowest unoccupied molecular orbital (LUMO), which enables air stability of excess electrons. In this work, a series of naphthalene diimide (NDI) copolymers with varying highest occupied molecular orbital (HOMO) and LUMO energy levels are made and used to investigate photochemically and thermally induced electron transfer from a small molecule NDI carrying dimethylaminopropyl (DMAP) side chains. Density functional theory calculations and UV-vis and electron spin resonance (ESR) spectroscopies indicate that the LUMO energy level of the NDI copolymer governs thermal electron transfer from the HOMO of the DMAP side chain and dictates air stability of the corresponding radical anions. Conversely, photoinduced electron transfer from DMAP to the NDI copolymer is governed by the position of the HOMO energy levels. Although the dicyano-substituted NDI copolymers with very low LUMO levels display the highest radical anion yield and excellent air stability, their conductivity is limited by electron mobility, which in turn is strongly influenced by backbone torsion and localized radical anions. These results establish fundamental structure-function relationships and shine light on the use of simple, cost-effective, covalently bound tertiary amines as potential n-dopants for electron-acceptor copolymers.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Schmidt, Simon B. UNSPECIFIED UNSPECIFIED UNSPECIFIED Hoenig, Markus UNSPECIFIED UNSPECIFIED UNSPECIFIED Shin, Younghun UNSPECIFIED UNSPECIFIED UNSPECIFIED Cassinelli, Marco UNSPECIFIED UNSPECIFIED UNSPECIFIED Perinot, Andrea UNSPECIFIED UNSPECIFIED UNSPECIFIED Caironi, Mario UNSPECIFIED orcid.org/0000-0002-0442-4439 UNSPECIFIED Jiao, Xuechen UNSPECIFIED orcid.org/0000-0001-7387-0275 UNSPECIFIED McNeill, Christopher R. UNSPECIFIED orcid.org/0000-0001-5221-878X UNSPECIFIED Fazzi, Daniele UNSPECIFIED orcid.org/0000-0002-8515-4214 UNSPECIFIED Biskup, Till UNSPECIFIED orcid.org/0000-0003-2913-0004 UNSPECIFIED Sommer, Michael UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-335166
DOI:	10.1021/acsapm.0c00151
Journal or Publication Title:	ACS Appl. Polym. Mater.
Volume:	2
Number:	5
Page Range:	S. 1954 - 1964
Date:	2020
Publisher:	AMER CHEMICAL SOC
Place of Publication:	WASHINGTON
ISSN:	2637-6105
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Physical Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language ORGANIC SEMICONDUCTORS; CONJUGATED POLYMERS; HIGH-PERFORMANCE; BUILDING-BLOCKS; ARYLATION; CHANNEL; THIOPHENE; DOPANTS; DESIGN; STATES Multiple languages Materials Science, Multidisciplinary; Polymer Science Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/33516