Synthesis of an Electrodeficient Dipyridylbenzene-like Terdentate Ligand: Cyclometallating Ligand for Highly Emitting Iridium(III) and Platinum(II) Complexes
Cyclometallated iridium(III) and platinum(II) complexes are intensely used in optoelectronics for their photophysical properties and ability to convert excitons from singlet to triplet state, thus improving the device efficiency. In this contribution, we report the multi-steps synthesis of an electr...
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| Format: | Article |
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MDPI AG
2023-07-01
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| Series: | Organics |
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| Online Access: | https://www.mdpi.com/2673-401X/4/3/29 |
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| author | Pierre-Henri Lanoë Christian Philouze Frédérique Loiseau |
| author_facet | Pierre-Henri Lanoë Christian Philouze Frédérique Loiseau |
| author_sort | Pierre-Henri Lanoë |
| collection | DOAJ |
| description | Cyclometallated iridium(III) and platinum(II) complexes are intensely used in optoelectronics for their photophysical properties and ability to convert excitons from singlet to triplet state, thus improving the device efficiency. In this contribution, we report the multi-steps synthesis of an electrodeficient dipyridylbenzene-like terdentate ligand [N^C^N], namely 2′,6′-dimethyl-2,3′:5′,2″-terpyridine (<b>6</b>), with 18% overall yield. Compound <b>6</b> has been employed to synthesize two phosphorescent complexes of platinum(II) and iridium(III), namely compounds <b>7</b> and <b>8,</b> respectively. Both complexes have been characterized by NMR and high resolution mass spectrometry, and demonstrate high luminescence quantum yields in a deaerated solution at room temperature, with 18% and 61% for <b>7</b> and <b>8,</b> respectively. If the iridium(III) complex displays similar emission properties to [Ir(dpyx)(ppy)Cl] (dpyx = 3,5-dimethyl-2,6-dipyridylbenzene and ppy = 2- phenylpyridine), the platinum(II) derivative, with λ<sub>em</sub> = 470 nm, is a rare example of a fluorine atom-free blue emitting [N^C^N]PtCl complex. |
| first_indexed | 2024-03-10T22:19:49Z |
| format | Article |
| id | doaj.art-ec4f86ce4f71404895aad77aed942248 |
| institution | Directory Open Access Journal |
| issn | 2673-401X |
| language | English |
| last_indexed | 2024-03-10T22:19:49Z |
| publishDate | 2023-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Organics |
| spelling | doaj.art-ec4f86ce4f71404895aad77aed9422482023-11-19T12:20:57ZengMDPI AGOrganics2673-401X2023-07-014340341610.3390/org4030029Synthesis of an Electrodeficient Dipyridylbenzene-like Terdentate Ligand: Cyclometallating Ligand for Highly Emitting Iridium(III) and Platinum(II) ComplexesPierre-Henri Lanoë0Christian Philouze1Frédérique Loiseau2CNRS, DCM, Univ. Grenoble Alpes, 38000 Grenoble, FranceCNRS, DCM, Univ. Grenoble Alpes, 38000 Grenoble, FranceCNRS, DCM, Univ. Grenoble Alpes, 38000 Grenoble, FranceCyclometallated iridium(III) and platinum(II) complexes are intensely used in optoelectronics for their photophysical properties and ability to convert excitons from singlet to triplet state, thus improving the device efficiency. In this contribution, we report the multi-steps synthesis of an electrodeficient dipyridylbenzene-like terdentate ligand [N^C^N], namely 2′,6′-dimethyl-2,3′:5′,2″-terpyridine (<b>6</b>), with 18% overall yield. Compound <b>6</b> has been employed to synthesize two phosphorescent complexes of platinum(II) and iridium(III), namely compounds <b>7</b> and <b>8,</b> respectively. Both complexes have been characterized by NMR and high resolution mass spectrometry, and demonstrate high luminescence quantum yields in a deaerated solution at room temperature, with 18% and 61% for <b>7</b> and <b>8,</b> respectively. If the iridium(III) complex displays similar emission properties to [Ir(dpyx)(ppy)Cl] (dpyx = 3,5-dimethyl-2,6-dipyridylbenzene and ppy = 2- phenylpyridine), the platinum(II) derivative, with λ<sub>em</sub> = 470 nm, is a rare example of a fluorine atom-free blue emitting [N^C^N]PtCl complex.https://www.mdpi.com/2673-401X/4/3/29ligand synthesisphosphorescenceplatinumiridiumblue emissioncyclometallating coordination |
| spellingShingle | Pierre-Henri Lanoë Christian Philouze Frédérique Loiseau Synthesis of an Electrodeficient Dipyridylbenzene-like Terdentate Ligand: Cyclometallating Ligand for Highly Emitting Iridium(III) and Platinum(II) Complexes Organics ligand synthesis phosphorescence platinum iridium blue emission cyclometallating coordination |
| title | Synthesis of an Electrodeficient Dipyridylbenzene-like Terdentate Ligand: Cyclometallating Ligand for Highly Emitting Iridium(III) and Platinum(II) Complexes |
| title_full | Synthesis of an Electrodeficient Dipyridylbenzene-like Terdentate Ligand: Cyclometallating Ligand for Highly Emitting Iridium(III) and Platinum(II) Complexes |
| title_fullStr | Synthesis of an Electrodeficient Dipyridylbenzene-like Terdentate Ligand: Cyclometallating Ligand for Highly Emitting Iridium(III) and Platinum(II) Complexes |
| title_full_unstemmed | Synthesis of an Electrodeficient Dipyridylbenzene-like Terdentate Ligand: Cyclometallating Ligand for Highly Emitting Iridium(III) and Platinum(II) Complexes |
| title_short | Synthesis of an Electrodeficient Dipyridylbenzene-like Terdentate Ligand: Cyclometallating Ligand for Highly Emitting Iridium(III) and Platinum(II) Complexes |
| title_sort | synthesis of an electrodeficient dipyridylbenzene like terdentate ligand cyclometallating ligand for highly emitting iridium iii and platinum ii complexes |
| topic | ligand synthesis phosphorescence platinum iridium blue emission cyclometallating coordination |
| url | https://www.mdpi.com/2673-401X/4/3/29 |
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