Electrochemical and Spectroelectrochemical Comparative Study of Macrocyclic Thermally Activated Delayed Fluorescent Compounds: Molecular Charge Stability vs OLED EQE Roll-Off

Nyga, Aleksandra; Izumi, Saika; Higginbotham, Heather F.; Stachelek, Patrycja; Pluczyk, Sandra; de Silva, Piotr; Minakata, Satoshi; Takeda, Youhei; Data, Przemyslaw

doi:https://doi.org/10.1002/ajoc.202000475

Electrochemical and Spectroelectrochemical Comparative Study of Macrocyclic Thermally Activated Delayed Fluorescent Compounds: Molecular Charge Stability vs OLED EQE Roll-Off

Nyga, Aleksandra; Izumi, Saika; Higginbotham, Heather F. et al.

Asian Journal of Organic Chemistry, 2020, 9(12), 2153-2161

Number of Access:796（2025-07-27 08:51 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/78808

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Title	Electrochemical and Spectroelectrochemical Comparative Study of Macrocyclic Thermally Activated Delayed Fluorescent Compounds: Molecular Charge Stability vs OLED EQE Roll-Off
Creator	CreatorName Nyga, Aleksandra
	CreatorName Izumi, Saika
	CreatorName Higginbotham, Heather F.
	CreatorName Stachelek, Patrycja
	CreatorName Pluczyk, Sandra
	CreatorName de Silva, Piotr
	NRID 1000090273599 1000090273599 researchmap permalink read0185263 read0185263 Scopus Author ID 7003640913 7003640913 ORCID 0000-0001-9619-445X 0000-0001-9619-445X CreatorName Minakata, Satoshi
	NRID 1000060608785 1000060608785 ORCID 0000-0001-9103-4238 0000-0001-9103-4238 researchmap permalink read0156438 read0156438 Scopus Author ID 12753487600 12753487600 CreatorName Takeda, Youhei
	CreatorName Data, Przemyslaw
Subject	electrochemistry
	macrocycles
	organic light-emitting diodes
	redox
	thermally activated delayed fluorescence
Description	This is the peer reviewed version of the following article: A. Nyga, S. Izumi, H. F. Higginbotham, P. Stachelek, S. Pluczyk, P. de Silva, S. Minakata, Y. Takeda, P. Data, Asian J. Org. Chem. 2020, 9, 2153., which has been published in final form at https://doi.org/10.1002/ajoc.202000475. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Abstract	In this work, we present how a small change in molecular structure can affect the electrochemical stability of organic compounds. A new electron donor-acceptor-donor-acceptor (D-A-D-A) macrocyclic π-conjugated compound (tBuMC) comprising of dibenzophenazine as As and N,N’-bis(t-butylphenyl)-p-phenylenediamines as Ds has been synthesized. The photophysical investigation uncovered that tBuMC showed thermally activated delayed fluorescence and that the organic light-emitting diodes (OLEDs) fabricated with tBuMC as the emitter achieved high external quantum efficiency (EQEs) of ca. 10%. However, the OLED with tBuMC showed a slightly lower EQE than that of the OLED with MC (11.6%) and showed greater EQE roll-off. Comparative studies on electrochemical properties of tBuMC, MC, and a linear analogue (Linear) revealed the introduction of t-Bu groups in the D-A-D-A scaffold causes a significant change in redox behavior. Full electrochemical and spectroelectrochemical studies gave clues to understand how the steric hindering group is affecting the charge distribution in the new molecules which results in a significant difference in the OLED roll-off. The electrochemical investigations together with UV-Vis-NIR and EPR analyses supported by quantum chemical theoretical calculations were performed, which provided us insights on the effect of structural modification on the redox properties of the D-A-D-A scaffold.
Publisher	Wiley-VCH Verlag
Source Title	Asian Journal of Organic Chemistry
Volume (Issue)	9(12)
Page	2153-2161
Date of Issued	2020-12-11
Language	English
Handle URL	https://hdl.handle.net/11094/78808
PISSN	21935807
NCID	AA12586329
Relation.isVersionOf	DOI (Publisher Version) https://doi.org/10.1002/ajoc.202000475
Access Rights	open access
oaire:version	Accepted Manuscript
Category	学術雑誌論文 Journal Article

Resource Type	journal article
Local Type	Journal Article
DCMI Type	Text
DCTERMS.bibliographicCitation	Asian Journal of Organic Chemistry. 2020, 9(12), p. 2153-2161
DC.title	Electrochemical and Spectroelectrochemical Comparative Study of Macrocyclic Thermally Activated Delayed Fluorescent Compounds: Molecular Charge Stability vs OLED EQE Roll-Off
DC.creator	Nyga, Aleksandra
	Izumi, Saika
	Higginbotham, Heather F.
	Stachelek, Patrycja
	Pluczyk, Sandra
	de Silva, Piotr
	Minakata, Satoshi
	Takeda, Youhei
	Data, Przemyslaw
DC.publisher	Wiley-VCH Verlag
DC.language' scheme='DCTERMS.RFC1766	English
DC.type' scheme='DCTERMS.DCMIType	Text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2020-12-11
DC.identifier	https://doi.org/10.1002/ajoc.202000475
DC.subject	electrochemistry
	macrocycles
	organic light-emitting diodes
	redox
	thermally activated delayed fluorescence
DC.description	This is the peer reviewed version of the following article: A. Nyga, S. Izumi, H. F. Higginbotham, P. Stachelek, S. Pluczyk, P. de Silva, S. Minakata, Y. Takeda, P. Data, Asian J. Org. Chem. 2020, 9, 2153., which has been published in final form at https://doi.org/10.1002/ajoc.202000475. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
DCTERMS.abstract	In this work, we present how a small change in molecular structure can affect the electrochemical stability of organic compounds. A new electron donor-acceptor-donor-acceptor (D-A-D-A) macrocyclic π-conjugated compound (tBuMC) comprising of dibenzophenazine as As and N,N’-bis(t-butylphenyl)-p-phenylenediamines as Ds has been synthesized. The photophysical investigation uncovered that tBuMC showed thermally activated delayed fluorescence and that the organic light-emitting diodes (OLEDs) fabricated with tBuMC as the emitter achieved high external quantum efficiency (EQEs) of ca. 10%. However, the OLED with tBuMC showed a slightly lower EQE than that of the OLED with MC (11.6%) and showed greater EQE roll-off. Comparative studies on electrochemical properties of tBuMC, MC, and a linear analogue (Linear) revealed the introduction of t-Bu groups in the D-A-D-A scaffold causes a significant change in redox behavior. Full electrochemical and spectroelectrochemical studies gave clues to understand how the steric hindering group is affecting the charge distribution in the new molecules which results in a significant difference in the OLED roll-off. The electrochemical investigations together with UV-Vis-NIR and EPR analyses supported by quantum chemical theoretical calculations were performed, which provided us insights on the effect of structural modification on the redox properties of the D-A-D-A scaffold.
DC.format	78808
citation_title	Electrochemical and Spectroelectrochemical Comparative Study of Macrocyclic Thermally Activated Delayed Fluorescent Compounds: Molecular Charge Stability vs OLED EQE Roll-Off
citation_author	Nyga, Aleksandra
	Izumi, Saika
	Higginbotham, Heather F.
	Stachelek, Patrycja
	Pluczyk, Sandra
	de Silva, Piotr
	Minakata, Satoshi
	Takeda, Youhei
	Data, Przemyslaw
citation_publisher	Wiley-VCH Verlag
citation_language	English
citation_date	2020-12-11
citation_journal_title	Asian Journal of Organic Chemistry
citation_volume	9
citation_issue	12
citation_firstpage	2153
citation_lastpage	2161
citation_doi	https://doi.org/10.1002/ajoc.202000475
citation_public_url	https://hdl.handle.net/11094/78808

Electrochemical and Spectroelectrochemical Comparative Study of Macrocyclic Thermally Activated Delayed Fluorescent Compounds: Molecular Charge Stability vs OLED EQE Roll-Off

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