Styrylpyrimidine chromophores with bulky electron-donating substituents: experimental and theoretical investigation
In: ISSN: 1463-9076, 2023
Online
academicJournal
Zugriff:
International audience ; Styrylpyrimidine with bulky 9,9-dimethylacridan, phenoxazine and phenothiazine electron-donating fragment were designed. Thermally activated delayed fluorescence (TADF) properties were expected for these structures. These chromophores exhibit peculiar emission properties. For 9,9-dimethylacridan and phenoxazine derivatives, a single emission highly sensitive to the polarity is observed in solution whereas for phenothiazine derivative a dual emission is observed in solution and is attributed to the coexistence of quasi-axial (Qax) and quasi-equatorial (Qeq) conformers. This study intends to understand with theoretical and experimental works, why the studied chromophores do not exhibit TADF properties, contrary to what was expected. The absence of phosphorescence both at room temperature and 77K tends to indicate the impossibility to harvest triplet states in these systems. Wave-function based calculations show that for both conformers of the three chromophores the S1-T1 splitting is significantly larger than 0.2 eV. The second triplet state T2 of Qeq conformers is found very close in energy to the singlet S1 state, but S1 and T2 states possess similar charge transfer characters. This prevents efficient spin-orbit coupling between the states, which is consistent with the absence of TADF.
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Styrylpyrimidine chromophores with bulky electron-donating substituents: experimental and theoretical investigation
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Autor/in / Beteiligte Person: | Hodée, Maxime ; Massue, Julien ; Achelle, Sylvain ; Fihey, Arnaud ; Tondelier, Denis ; Ulrich, Gilles ; Le Guen, Françoise Robin ; Katan, Claudine ; Institut des Sciences Chimiques de Rennes (ISCR) ; Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes) ; Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS) ; Institut de chimie et procédés pour l'énergie, l'environnement et la santé (ICPEES) ; Université de Strasbourg (UNISTRA)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE) ; Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS) ; Laboratoire de physique des interfaces et des couches minces Palaiseau (LPICM) ; École polytechnique (X)-Centre National de la Recherche Scientifique (CNRS) ; ANR-18-EURE-0012,LumoMat-E,Molecular Materials for Organic Electronics/Photonics(2018) |
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Zeitschrift: | ISSN: 1463-9076, 2023 |
Veröffentlichung: | HAL CCSD ; Royal Society of Chemistry, 2023 |
Medientyp: | academicJournal |
DOI: | 10.1039/D3CP03705C |
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