Synthesis and evaluation of new isoquinoline diimide derivatives as small molecule acceptors for organic solar cells

Insuasty, A; Carrara, S; Vu, D; Montalvo-Acosta, JJ; Ortíz, A; Hogan, C; McNeill, CR; Langford, SJ

Synthesis and evaluation of new isoquinoline diimide derivatives as small molecule acceptors for organic solar cells

Insuasty, A Carrara, S Vu, D Montalvo-Acosta, JJ Ortíz, A Hogan, C McNeill, CR Langford, SJ

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Publisher:: Elsevier
Publication Type:: Journal Article
Citation:: Tetrahedron, 2025, 178, pp. 134616
Issue Date:: 2025-06-01

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Field	Value	Language
dc.contributor.author	Insuasty, A
dc.contributor.author	Carrara, S
dc.contributor.author	Vu, D
dc.contributor.author	Montalvo-Acosta, JJ
dc.contributor.author	Ortíz, A
dc.contributor.author	Hogan, C
dc.contributor.author	McNeill, CR
dc.contributor.author	Langford, SJ
dc.date.accessioned	2025-10-15T03:49:19Z
dc.date.available	2025-10-15T03:49:19Z
dc.date.issued	2025-06-01
dc.identifier.citation	Tetrahedron, 2025, 178, pp. 134616
dc.identifier.issn	0040-4020
dc.identifier.issn	1464-5416
dc.identifier.uri	http://hdl.handle.net/10453/190403
dc.description.abstract	In this work we explore the use of the method of oxidation and heterocyclization of naphthalene diimides (NDIs) to obtain five novel isoquinoline diimide derivatives (IQDI 3–7) as new small molecule acceptors. These derivatives comprise a main core based on triphenylamine (TPA) as electron-donor linked to an isoquinoline diimide moiety as a new electron-acceptor (IQDI 3). The effect on the electronic properties of a further functionalization on TPA achieving A-D-A architectures with additional electron acceptors moieties such as carbonyl group (IQDI 4), 3-methylrhodanine (IQDI 5), 1,3-indandione (IQDI 6) and malononitrile (IQDI 7) was studied. Their electrochemical and optoelectronic properties as well as their performance in photovoltaic devices using J52 as electron-donor polymer were studied being IQDI 6 the compound that showed the best PCE % value.
dc.language	en
dc.publisher	Elsevier
dc.relation	http://purl.org/au-research/grants/arc/DP170102145
dc.relation.ispartof	Tetrahedron
dc.relation.isbasedon	10.1016/j.tet.2025.134616
dc.rights	info:eu-repo/semantics/openAccess
dc.subject	0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry
dc.subject.classification	Organic Chemistry
dc.subject.classification	3101 Biochemistry and cell biology
dc.subject.classification	3404 Medicinal and biomolecular chemistry
dc.subject.classification	3405 Organic chemistry
dc.title	Synthesis and evaluation of new isoquinoline diimide derivatives as small molecule acceptors for organic solar cells
dc.type	Journal Article
utslib.citation.volume	178
utslib.for	0304 Medicinal and Biomolecular Chemistry
utslib.for	0305 Organic Chemistry
pubs.organisational-group	University of Technology Sydney
pubs.organisational-group	University of Technology Sydney/Faculty of Science
pubs.organisational-group	University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	University of Technology Sydney/UTS Groups
pubs.organisational-group	University of Technology Sydney/UTS Groups/Centre for Clean Energy Technology (CCET)
utslib.copyright.status	open_access	*
dc.rights.license	This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND 4.0). To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-nd/4.0/
dc.date.updated	2025-10-15T03:49:15Z
pubs.publication-status	Published
pubs.volume	178

Abstract:

In this work we explore the use of the method of oxidation and heterocyclization of naphthalene diimides (NDIs) to obtain five novel isoquinoline diimide derivatives (IQDI 3–7) as new small molecule acceptors. These derivatives comprise a main core based on triphenylamine (TPA) as electron-donor linked to an isoquinoline diimide moiety as a new electron-acceptor (IQDI 3). The effect on the electronic properties of a further functionalization on TPA achieving A-D-A architectures with additional electron acceptors moieties such as carbonyl group (IQDI 4), 3-methylrhodanine (IQDI 5), 1,3-indandione (IQDI 6) and malononitrile (IQDI 7) was studied. Their electrochemical and optoelectronic properties as well as their performance in photovoltaic devices using J52 as electron-donor polymer were studied being IQDI 6 the compound that showed the best PCE % value.

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http://hdl.handle.net/10453/190403