Nonalternant Extension of Multiple Resonance Emitter via Palladium-Catalyzed [5+2]-Annulation
Despite the proliferation of multiple resonance (MR) emitters with rigid 1,4-borazine-based skeletons, the straightforward and efficient incorporation of nonhexagonal rings, especially for heptagons, to avoid notorious aggregation-induced quenching effect remains elusive. Here, a green-yellow emitte...
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| Format: | Article |
| Language: | English |
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Georg Thieme Verlag
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| Series: | Organic Materials |
| Online Access: | http://www.thieme-connect.de/DOI/DOI?10.1055/a-2531-9798 |
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| author | Weiwen Zhuang Waiming Chong Junzhi Liu |
| author_facet | Weiwen Zhuang Waiming Chong Junzhi Liu |
| author_sort | Weiwen Zhuang |
| collection | DOAJ |
| description | Despite the proliferation of multiple resonance (MR) emitters with rigid 1,4-borazine-based skeletons, the straightforward and efficient incorporation of nonhexagonal rings, especially for heptagons, to avoid notorious aggregation-induced quenching effect remains elusive. Here, a green-yellow emitter consisting of two azepines was designed and synthesized via a palladium-catalyzed one-pot twofold [5+2]-annulation reaction with high selectivity and efficiency. The tetrabenzene-fused benzo[1,2-b:5,4-b']bis(azepine) (TBBBA) core induced a highly twisted and dynamically helical rim for the novel MR-skeleton, which reduced Π-Π stacking in the solid state. Moreover, the nonalternant topology facilitated the delocalization of frontier molecular orbitals (FMO) within the twisted geometry, thus achieving red-shifted narrow emission. Our work provides a new synthetic strategy towards nonalternant extension of MR-emitters and gives insights into the electronic effects of multiple azepination on FMO distribution. |
| format | Article |
| id | doaj-art-eb376f1cfa274bb4838663331f4f966a |
| institution | Kabale University |
| issn | 2625-1825 |
| language | English |
| publisher | Georg Thieme Verlag |
| record_format | Article |
| series | Organic Materials |
| spelling | doaj-art-eb376f1cfa274bb4838663331f4f966a2025-02-05T00:00:57ZengGeorg Thieme VerlagOrganic Materials2625-182510.1055/a-2531-9798Nonalternant Extension of Multiple Resonance Emitter via Palladium-Catalyzed [5+2]-AnnulationWeiwen Zhuang0Waiming Chong1Junzhi Liu2https://orcid.org/0000-0001-7146-0942Chemistry, The University of Hong Kong, Hong Kong, Hong KongChemistry, The University of Hong Kong, Hong Kong, Hong KongChemistry, University of Hong KongDespite the proliferation of multiple resonance (MR) emitters with rigid 1,4-borazine-based skeletons, the straightforward and efficient incorporation of nonhexagonal rings, especially for heptagons, to avoid notorious aggregation-induced quenching effect remains elusive. Here, a green-yellow emitter consisting of two azepines was designed and synthesized via a palladium-catalyzed one-pot twofold [5+2]-annulation reaction with high selectivity and efficiency. The tetrabenzene-fused benzo[1,2-b:5,4-b']bis(azepine) (TBBBA) core induced a highly twisted and dynamically helical rim for the novel MR-skeleton, which reduced Π-Π stacking in the solid state. Moreover, the nonalternant topology facilitated the delocalization of frontier molecular orbitals (FMO) within the twisted geometry, thus achieving red-shifted narrow emission. Our work provides a new synthetic strategy towards nonalternant extension of MR-emitters and gives insights into the electronic effects of multiple azepination on FMO distribution.http://www.thieme-connect.de/DOI/DOI?10.1055/a-2531-9798 |
| spellingShingle | Weiwen Zhuang Waiming Chong Junzhi Liu Nonalternant Extension of Multiple Resonance Emitter via Palladium-Catalyzed [5+2]-Annulation Organic Materials |
| title | Nonalternant Extension of Multiple Resonance Emitter via Palladium-Catalyzed [5+2]-Annulation |
| title_full | Nonalternant Extension of Multiple Resonance Emitter via Palladium-Catalyzed [5+2]-Annulation |
| title_fullStr | Nonalternant Extension of Multiple Resonance Emitter via Palladium-Catalyzed [5+2]-Annulation |
| title_full_unstemmed | Nonalternant Extension of Multiple Resonance Emitter via Palladium-Catalyzed [5+2]-Annulation |
| title_short | Nonalternant Extension of Multiple Resonance Emitter via Palladium-Catalyzed [5+2]-Annulation |
| title_sort | nonalternant extension of multiple resonance emitter via palladium catalyzed 5 2 annulation |
| url | http://www.thieme-connect.de/DOI/DOI?10.1055/a-2531-9798 |
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