Publicação
A thorough and comprehensive study of novel phthaloperinone derivatives
| Resumo: | Despite 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. |
|---|---|
| Autores principais: | Amorim, Ana C. |
| Outros Autores: | Morgado, Jorge; Ramalho, João P. Prates; Cruz, Hugo; Cunha, Carla; Paixão, José A.; Melo, J. Sérgio Seixas de; Lopes, Susana M. M.; Branco, Luís C.; Burke, Anthony J. |
| Assunto: | Chemistry (miscellaneous) General Materials Science |
| Ano: | 2025 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Universidade Nova de Lisboa |
| Idioma: | inglês |
| Origem: | Repositório Institucional da UNL |
| _version_ | 1879446224578281472 |
|---|---|
| author | Amorim, Ana C. |
| author2 | Morgado, Jorge Ramalho, João P. Prates Cruz, Hugo Cunha, Carla Paixão, José A. Melo, J. Sérgio Seixas de Lopes, Susana M. M. Branco, Luís C. Burke, Anthony J. |
| author2_role | author author author author author author author author author |
| author_facet | Amorim, Ana C. Morgado, Jorge Ramalho, João P. Prates Cruz, Hugo Cunha, Carla Paixão, José A. Melo, J. Sérgio Seixas de Lopes, Susana M. M. Branco, Luís C. Burke, Anthony J. |
| author_role | author |
| contributor_name_str_mv | LAQV@REQUIMTE DQ - Departamento de Química RSC - Royal Society of Chemistry RUN |
| country_str | PT |
| creators_json_txt | [{\"Person.name\":\"Amorim, Ana C.\"},{\"Person.name\":\"Morgado, Jorge\"},{\"Person.name\":\"Ramalho, João P. Prates\"},{\"Person.name\":\"Cruz, Hugo\"},{\"Person.name\":\"Cunha, Carla\"},{\"Person.name\":\"Paixão, José A.\"},{\"Person.name\":\"Melo, J. Sérgio Seixas de\"},{\"Person.name\":\"Lopes, Susana M. M.\"},{\"Person.name\":\"Branco, Luís C.\"},{\"Person.name\":\"Burke, Anthony J.\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | LAQV@REQUIMTE DQ - Departamento de Química RSC - Royal Society of Chemistry RUN |
| datacite.creators.creator.creatorName.fl_str_mv | Amorim, Ana C. Morgado, Jorge Ramalho, João P. Prates Cruz, Hugo Cunha, Carla Paixão, José A. Melo, J. Sérgio Seixas de Lopes, Susana M. M. Branco, Luís C. Burke, Anthony J. |
| datacite.date.Accepted.fl_str_mv | 2025-12-21T00:00:00Z |
| datacite.date.available.fl_str_mv | 2026-01-30T15:00:01Z |
| datacite.date.embargoed.fl_str_mv | 2026-01-30T15:00:01Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | Chemistry (miscellaneous) General Materials Science |
| datacite.titles.title.fl_str_mv | A thorough and comprehensive study of novel phthaloperinone derivatives from synthesis and property evaluation to applications in light-emitting diodes |
| dc.contributor.none.fl_str_mv | LAQV@REQUIMTE DQ - Departamento de Química RSC - Royal Society of Chemistry RUN |
| dc.creator.none.fl_str_mv | Amorim, Ana C. Morgado, Jorge Ramalho, João P. Prates Cruz, Hugo Cunha, Carla Paixão, José A. Melo, J. Sérgio Seixas de Lopes, Susana M. M. Branco, Luís C. Burke, Anthony J. |
| dc.date.Accepted.fl_str_mv | 2025-12-21T00:00:00Z |
| dc.date.available.fl_str_mv | 2026-01-30T15:00:01Z |
| dc.date.embargoed.fl_str_mv | 2026-01-30T15:00:01Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | http://hdl.handle.net/10362/199879 |
| dc.language.none.fl_str_mv | eng |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.subject.none.fl_str_mv | Chemistry (miscellaneous) General Materials Science |
| dc.title.fl_str_mv | A thorough and comprehensive study of novel phthaloperinone derivatives from synthesis and property evaluation to applications in light-emitting diodes |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | Despite 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. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | article |
| fulltext.url.fl_str_mv | https://run.unl.pt/bitstreams/a3803ff3-c98c-41b3-a202-f4cd1550b079/download |
| id | run_f976d24556fc57b097403be0c5e21b34 |
| identifier.url.fl_str_mv | http://hdl.handle.net/10362/199879 |
| inst_facet_str | urn:organizationAcronym:unl{{{_:::_}}}Universidade Nova de Lisboa |
| instacron_str | unl |
| institution | Universidade Nova de Lisboa |
| instname_str | Universidade Nova de Lisboa |
| language | eng |
| network_acronym_str | run |
| network_name_str | Repositório Institucional da UNL |
| oai_identifier_str | oai:run.unl.pt:10362/199879 |
| organization_str_mv | urn:organizationAcronym:unl |
| person_str_mv | Amorim, Ana C. Morgado, Jorge Ramalho, João P. Prates Cruz, Hugo Cunha, Carla Paixão, José A. Melo, J. Sérgio Seixas de Lopes, Susana M. M. Branco, Luís C. Burke, Anthony J. |
| publishDate | 2025 |
| repo_facet_str | urn:repositoryAcronym:run{{{_:::_}}}Repositório Institucional da UNL |
| reponame_str | Repositório Institucional da UNL |
| repository_id_str | urn:repositoryAcronym:run |
| service_str_mv | urn:repositoryAcronym:run |
| spelling | engenDespite 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.application/pdfenA thorough and comprehensive study of novel phthaloperinone derivativesSubtitleenfrom synthesis and property evaluation to applications in light-emitting diodesAmorim, Ana C.Morgado, JorgeRamalho, João P. PratesCruz, HugoCunha, CarlaPaixão, José A.Melo, J. Sérgio Seixas deLopes, Susana M. M.Branco, Luís C.Burke, Anthony J.LAQV@REQUIMTEDQ - Departamento de QuímicaRSC - Royal Society of ChemistryHostingInstitutionOrganizationalRUNe-mailmailto:run@unl.ptrun@unl.ptISSNIsPartOf2633-5409URNIsPartOfPURE: 151570683URNIsPartOfPURE UUID: 82583431-add0-46b2-9592-c149d32522f7URNIsPartOfScopus: 105024549662URNIsPartOfWOS: 001606138400001URNIsPartOfORCID: /0000-0002-1047-7342/work/220581081DOIIsPartOf10.1039/d5ma00761e2026-01-30T15:00:01Z2025-12-212025-12-21T00:00:00ZHandlehttp://hdl.handle.net/10362/199879http://purl.org/coar/access_right/c_abf2open accessChemistry (miscellaneous)General Materials Science4363536 bytesliteraturehttp://purl.org/coar/resource_type/c_6501journal articlehttp://purl.org/coar/access_right/c_abf2application/pdffulltexthttps://run.unl.pt/bitstreams/a3803ff3-c98c-41b3-a202-f4cd1550b079/download |
| spellingShingle | A thorough and comprehensive study of novel phthaloperinone derivatives Amorim, Ana C. Chemistry (miscellaneous) General Materials Science |
| status | SINGLETON |
| subject.fl_str_mv | Chemistry (miscellaneous) General Materials Science |
| title | A thorough and comprehensive study of novel phthaloperinone derivatives |
| title_full | A thorough and comprehensive study of novel phthaloperinone derivatives |
| title_fullStr | A thorough and comprehensive study of novel phthaloperinone derivatives |
| title_full_unstemmed | A thorough and comprehensive study of novel phthaloperinone derivatives |
| title_short | A thorough and comprehensive study of novel phthaloperinone derivatives |
| title_sort | A thorough and comprehensive study of novel phthaloperinone derivatives |
| topic | Chemistry (miscellaneous) General Materials Science |
| topic_facet | Chemistry (miscellaneous) General Materials Science |
| url | http://hdl.handle.net/10362/199879 |
| visible | 1 |
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