Shortcut to highly p-extended optoelectronic systems based on the dibenzothiophene core
The Scholl reaction stands as a versatile tool to synthetize multiple p-extended systems via intramolecular C–C oxidative couplings. A prime example is the expansion of dibenzothiophene to polycyclic butterfly-shaped heterocycles, which claim key characteristics in diverse optoelectronic application...
| Autores: | , , , , , , , , |
|---|---|
| Tipo de recurso: | artículo |
| Fecha de publicación: | 2026 |
| País: | España |
| Institución: | Universitat Politècnica de Catalunya (UPC) |
| Repositorio: | UPCommons. Portal del coneixement obert de la UPC |
| Idioma: | inglés |
| OAI Identifier: | oai:upcommons.upc.edu:2117/450163 |
| Acceso en línea: | https://hdl.handle.net/2117/450163 https://dx.doi.org/10.1039/d5ma01124h |
| Access Level: | acceso abierto |
| Palabra clave: | Photovoltaic power generation Energia solar fotovoltaica Àrees temàtiques de la UPC::Energies::Energia solar fotovoltaica |
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Shortcut to highly p-extended optoelectronic systems based on the dibenzothiophene coreFabregat Pallejà, ClaraBujaldón Carbó, RogerOliva, SilviaGarcia Amoròs, JaumeVolyniuk, DmytroGhasemi, MelikaGrazulevicius, Juozas Vidas|||0000-0002-4408-9727Puigdollers i González, Joaquim|||0000-0002-1834-2565Velasco Castrillo, Maria DoloresPhotovoltaic power generationEnergia solar fotovoltaicaÀrees temàtiques de la UPC::Energies::Energia solar fotovoltaicaThe Scholl reaction stands as a versatile tool to synthetize multiple p-extended systems via intramolecular C–C oxidative couplings. A prime example is the expansion of dibenzothiophene to polycyclic butterfly-shaped heterocycles, which claim key characteristics in diverse optoelectronic applications. Herein we describe a protocol from commercial tetrabromothiophene based on sequential one-pot Suzuki–Miyaura reactions followed by the Scholl reaction. This strategy permits rapid access to complex constructions fusing up to 11 rings in just two steps and improved yields. The proposed p-extensions successfully reduced the HOMO energy levels in the solid state to align with the gold work function (5.1 eV), while offering tunable photophysical properties. Remarkably, phenanthrene as scaffold endowed the core with a hole mobility value of 7 × 10-5 cm2 V-1 s-1 in OTFTs and excellent air-stability, with a shelf lifetime exceeding one year. Moreover, the inclusion of sulfurated units unlocked room temperature phosphorescence under oxygen-free conditions, a highly sought-after characteristic in metal- and halogen-free constructions. Their RTP quantum yields when introduced into a Zeonex matrix are as high as 14%, with oxygen-sensitive photoluminiscence that goes from deep-blue to yellow-orange. Altogether, this strategy holds great potential and versatility in developing adaptable materials for multiple functionalities.Authors gratefully acknowledge financial support by Ministerio de Ciencia, Innovacio´n y Universidades (grant number PID2023-151915NB-I00) and Horizon Europe, the European Union’s framework programme for research and innovation (R&I) for 2021–2027, project HELIOS (grant agreement no. 101155017). C. F. is grateful for the predoctoral grant FI AGAUR from Generalitat de Catalunya. The authors also want to thank the CCiTUB for the use of their equipment, and especially acknowledge Cristina Puigjaner (X-Ray Diffraction Unit) for the elucidation of the single-crystal structures and Ma Anto `nia Molins and Vicky Mun˜oz (NMR unit) for their assistance with 2D NMR spectroscopy.Peer ReviewedRoyal Society of Chemistry (RSC)20262026-01-1220262026-01-13journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/2117/450163https://dx.doi.org/10.1039/d5ma01124hreponame:UPCommons. Portal del coneixement obert de la UPCinstname:Universitat Politècnica de Catalunya (UPC)InglésengAgencia Estatal de Investigación http://doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023 PID2023-151915NB-I00 NUEVOS MATERIALES FOTOACTIVOS INTELIGENTESopen accesshttp://purl.org/coar/access_right/c_abf2Attribution-NonCommercial 4.0 Internationalhttp://creativecommons.org/licenses/by-nc/4.0/info:eu-repo/semantics/openAccessoai:upcommons.upc.edu:2117/4501632026-05-27T15:37:01Z |
| dc.title.none.fl_str_mv |
Shortcut to highly p-extended optoelectronic systems based on the dibenzothiophene core |
| title |
Shortcut to highly p-extended optoelectronic systems based on the dibenzothiophene core |
| spellingShingle |
Shortcut to highly p-extended optoelectronic systems based on the dibenzothiophene core Fabregat Pallejà, Clara Photovoltaic power generation Energia solar fotovoltaica Àrees temàtiques de la UPC::Energies::Energia solar fotovoltaica |
| title_short |
Shortcut to highly p-extended optoelectronic systems based on the dibenzothiophene core |
| title_full |
Shortcut to highly p-extended optoelectronic systems based on the dibenzothiophene core |
| title_fullStr |
Shortcut to highly p-extended optoelectronic systems based on the dibenzothiophene core |
| title_full_unstemmed |
Shortcut to highly p-extended optoelectronic systems based on the dibenzothiophene core |
| title_sort |
Shortcut to highly p-extended optoelectronic systems based on the dibenzothiophene core |
| dc.creator.none.fl_str_mv |
Fabregat Pallejà, Clara Bujaldón Carbó, Roger Oliva, Silvia Garcia Amoròs, Jaume Volyniuk, Dmytro Ghasemi, Melika Grazulevicius, Juozas Vidas|||0000-0002-4408-9727 Puigdollers i González, Joaquim|||0000-0002-1834-2565 Velasco Castrillo, Maria Dolores |
| author |
Fabregat Pallejà, Clara |
| author_facet |
Fabregat Pallejà, Clara Bujaldón Carbó, Roger Oliva, Silvia Garcia Amoròs, Jaume Volyniuk, Dmytro Ghasemi, Melika Grazulevicius, Juozas Vidas|||0000-0002-4408-9727 Puigdollers i González, Joaquim|||0000-0002-1834-2565 Velasco Castrillo, Maria Dolores |
| author_role |
author |
| author2 |
Bujaldón Carbó, Roger Oliva, Silvia Garcia Amoròs, Jaume Volyniuk, Dmytro Ghasemi, Melika Grazulevicius, Juozas Vidas|||0000-0002-4408-9727 Puigdollers i González, Joaquim|||0000-0002-1834-2565 Velasco Castrillo, Maria Dolores |
| author2_role |
author author author author author author author author |
| dc.subject.none.fl_str_mv |
Photovoltaic power generation Energia solar fotovoltaica Àrees temàtiques de la UPC::Energies::Energia solar fotovoltaica |
| topic |
Photovoltaic power generation Energia solar fotovoltaica Àrees temàtiques de la UPC::Energies::Energia solar fotovoltaica |
| description |
The Scholl reaction stands as a versatile tool to synthetize multiple p-extended systems via intramolecular C–C oxidative couplings. A prime example is the expansion of dibenzothiophene to polycyclic butterfly-shaped heterocycles, which claim key characteristics in diverse optoelectronic applications. Herein we describe a protocol from commercial tetrabromothiophene based on sequential one-pot Suzuki–Miyaura reactions followed by the Scholl reaction. This strategy permits rapid access to complex constructions fusing up to 11 rings in just two steps and improved yields. The proposed p-extensions successfully reduced the HOMO energy levels in the solid state to align with the gold work function (5.1 eV), while offering tunable photophysical properties. Remarkably, phenanthrene as scaffold endowed the core with a hole mobility value of 7 × 10-5 cm2 V-1 s-1 in OTFTs and excellent air-stability, with a shelf lifetime exceeding one year. Moreover, the inclusion of sulfurated units unlocked room temperature phosphorescence under oxygen-free conditions, a highly sought-after characteristic in metal- and halogen-free constructions. Their RTP quantum yields when introduced into a Zeonex matrix are as high as 14%, with oxygen-sensitive photoluminiscence that goes from deep-blue to yellow-orange. Altogether, this strategy holds great potential and versatility in developing adaptable materials for multiple functionalities. |
| publishDate |
2026 |
| dc.date.none.fl_str_mv |
2026 2026-01-12 2026 2026-01-13 |
| dc.type.none.fl_str_mv |
journal article http://purl.org/coar/resource_type/c_6501 VoR http://purl.org/coar/version/c_970fb48d4fbd8a85 |
| dc.type.openaire.fl_str_mv |
info:eu-repo/semantics/article |
| format |
article |
| dc.identifier.none.fl_str_mv |
https://hdl.handle.net/2117/450163 https://dx.doi.org/10.1039/d5ma01124h |
| url |
https://hdl.handle.net/2117/450163 https://dx.doi.org/10.1039/d5ma01124h |
| dc.language.none.fl_str_mv |
Inglés eng |
| language_invalid_str_mv |
Inglés |
| language |
eng |
| dc.relation.none.fl_str_mv |
Agencia Estatal de Investigación http://doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023 PID2023-151915NB-I00 NUEVOS MATERIALES FOTOACTIVOS INTELIGENTES |
| dc.rights.none.fl_str_mv |
open access http://purl.org/coar/access_right/c_abf2 Attribution-NonCommercial 4.0 International http://creativecommons.org/licenses/by-nc/4.0/ |
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info:eu-repo/semantics/openAccess |
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open access http://purl.org/coar/access_right/c_abf2 Attribution-NonCommercial 4.0 International http://creativecommons.org/licenses/by-nc/4.0/ |
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openAccess |
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application/pdf |
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Royal Society of Chemistry (RSC) |
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Royal Society of Chemistry (RSC) |
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reponame:UPCommons. Portal del coneixement obert de la UPC instname:Universitat Politècnica de Catalunya (UPC) |
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Universitat Politècnica de Catalunya (UPC) |
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