Cyclophane Molecules Exhibiting Thermally Activated Delayed Fluorescence: Linking Donor Units to Influence Molecular Conformation
| العنوان: | Cyclophane Molecules Exhibiting Thermally Activated Delayed Fluorescence: Linking Donor Units to Influence Molecular Conformation |
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| المؤلفون: | Andrei S. Batsanov, Jonathan S. Ward, Mark A. Fox, Fernando B. Dias, Alastair K Harrison, Matthias Hempe, Martin R. Bryce |
| المصدر: | Journal of organic chemistry, 2021, Vol.86(1), pp.429-445 [Peer Reviewed Journal] |
| بيانات النشر: | American Chemical Society (ACS), 2020. |
| سنة النشر: | 2020 |
| مصطلحات موضوعية: | 010405 organic chemistry, Stereochemistry, Organic Chemistry, 010402 general chemistry, 01 natural sciences, Fluorescence, 0104 chemical sciences, Williamson ether synthesis, chemistry.chemical_compound, Ring-closing metathesis, chemistry, Covalent bond, Phenothiazine, Excited state, Molecule, Cyclophane |
| الوصف: | The synthetic methodology to covalently link donors to form cyclophane-based thermally activated delayed fluorescence (TADF) molecules is presented. These are the first reported examples of TADF cyclophanes with “electronically innocent” bridges between the donor units. Using a phenothiazine-dibenzothiophene-S,S-dioxide donor–acceptor–donor (D–A–D) system, the two phenothiazine (PTZ) donor units were linked by three different strategies: (i) ester condensation, (ii) ether synthesis, and (iii) ring closing metathesis. Detailed X-ray crystallographic, photophysical and computational analyses show that the cyclophane molecular architecture alters the conformational distribution of the PTZ units, while retaining a certain degree of rotational freedom of the intersegmental D–A axes that is crucial for efficient TADF. Despite their different structures, the cyclophanes and their nonbridged precursors have similar photophysical properties since they emit through similar excited states resulting from the presence of the equatorial conformation of their PTZ donor segments. In particular, the axial–axial conformations, known to be detrimental to the TADF process, are suppressed by linking the PTZ units to form a cyclophane. The work establishes a versatile linking strategy that could be used in further functionalization while retaining the excellent photophysical properties of the parent D–A–D system. |
| وصف الملف: | application/pdf |
| تدمد: | 1520-6904 0022-3263 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7165cb7948642394b7a3686b830efac5 https://doi.org/10.1021/acs.joc.0c02174 |
| حقوق: | OPEN |
| رقم الأكسشن: | edsair.doi.dedup.....7165cb7948642394b7a3686b830efac5 |
| قاعدة البيانات: | OpenAIRE |
Find this issue from the American Chemical Society | تدمد: | 15206904 00223263 |
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