Logo do repositório
 
Publicação

A thorough and comprehensive study of novel phthaloperinone derivatives

2025-12-21Artigo científico Acesso aberto
Ver registo simples
dc.contributor.authorAmorim, Ana C.
dc.contributor.authorMorgado, Jorge
dc.contributor.authorRamalho, João P. Prates
dc.contributor.authorCruz, Hugo
dc.contributor.authorCunha, Carla
dc.contributor.authorPaixão, José A.
dc.contributor.authorMelo, J. Sérgio Seixas de
dc.contributor.authorLopes, Susana M. M.
dc.contributor.authorBranco, Luís C.
dc.contributor.authorBurke, Anthony J.
dc.contributor.institutionLAQV@REQUIMTE
dc.contributor.institutionDQ - Departamento de Química
dc.contributor.pblRSC - Royal Society of Chemistry
dc.date.accessioned2026-01-30T15:00:01Z
dc.date.available2026-01-30T15:00:01Z
dc.date.issued2025-12-21
dc.descriptionPublisher Copyright: This journal is © The Royal Society of Chemistry
dc.description.abstractDespite its promising electronic and semiconducting properties, 12H-phthaloperin-12-one remains a largely unexplored molecule, with limited studies regarding the impact of structural modifications on its properties and its application in light-emitting devices. To address this gap, we report the synthesis of 12 novel phthaloperinone derivatives, designed to fine-tune the photophysical, electrochemical, thermal and electroluminescence properties through the incorporation of electron-donating and electron-withdrawing substituents. The majority of substituents was found to interfere with the electronic distribution in the phthaloperinone core during the electronic excitation process. The introduction of a triphenylamine unit, as in compounds 3f/4f, resulted in the lowest energy gap of 2.22 eV, making this isomeric mixture a promising candidate for use as an organic semiconductor material. Electrochemical studies demonstrated that compounds 3e/4e–3h/4h and 3l/4l exhibited enhanced electrochemical stability, while thermal analysis showed that the pyrene-substituted derivative (3e/4e) displayed the highest thermal resistance (Td= 458 °C). Organic light-emitting diodes were fabricated to evaluate their electroluminescence properties. Compounds 3l/4l, which contain a phenyltriazolyl unit, achieved the best performance, displaying a maximum luminance of 99 cd m−2at 7.5 V, a luminous efficiency of 0.014 cd A−1, and a turn-on voltage of 3.3 V. These findings provide valuable insights into the structure–property relationships of phthaloperinone derivatives and highlight their potential for a wide range of applications, including electronic and optoelectronic devices.en
dc.description.versionpublishersversion
dc.description.versionpublished
dc.format.extent12
dc.format.extent4363536
dc.identifier.doi10.1039/d5ma00761e
dc.identifier.issn2633-5409
dc.identifier.otherPURE: 151570683
dc.identifier.otherPURE UUID: 82583431-add0-46b2-9592-c149d32522f7
dc.identifier.otherScopus: 105024549662
dc.identifier.otherWOS: 001606138400001
dc.identifier.otherORCID: /0000-0002-1047-7342/work/220581081
dc.identifier.urihttp://hdl.handle.net/10362/199879
dc.identifier.urlhttps://www.scopus.com/pages/publications/105024549662
dc.identifier.urlhttps://www.webofscience.com/wos/woscc/full-record/WOS:001606138400001
dc.language.isoeng
dc.peerreviewedyes
dc.subjectChemistry (miscellaneous)
dc.subjectGeneral Materials Science
dc.titleA thorough and comprehensive study of novel phthaloperinone derivativesen
dc.title.subtitlefrom synthesis and property evaluation to applications in light-emitting diodesen
dc.typejournal article
degois.publication.firstPage9556
degois.publication.issue24
degois.publication.lastPage9567
degois.publication.titleMaterials Advances
degois.publication.volume6
dspace.entity.typePublication
rcaap.rightsopenAccess

Ficheiros

Principais
A mostrar 1 - 1 de 1
Miniatura
Nome:
Amorim_et_al._2025_..pdf
Tamanho:
4.16 MB
Formato:
Adobe Portable Document Format
Ver/Abrir

Coleções

Home collection (FCT)