A novel carbazolophane : a comparison of the performance of two planar chiral CP-TADF emitters
Date
25/04/2024Author
Grant ID
EP/R035164/1
EP/W015137/1
EP/R035164/1
EP/W015137/1
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The prototypical example of a (cyclo)phane, [2.2]paracyclophane (PCP), has proven to be a versatile stereogenic moiety within the design of circularly polarized thermally activated delayed fluorescence (CP-TADF) emitters; however, the exploration of other cyclophanes within CP-TADF emitter design has been largely neglected. Here, a comparative study of the photophysical and optoelectronic properties of two cyclophane emitters, (1,7)tBuCzpPhTrz and its isomer (1,4)tBuCzpPhTrz, is presented. The carbazolophane-triazine compound (1,7)tBuCzpPhTrz, obtained via an unprecedented intramolecular rearrangement, is the first example of a planar chiral TADF emitter deviating from the PCP scaffold. Significant geometrical change of the enclosed carbazole in (1,7)tBuCzp results in an attenuation of the donor strength, while the merits of rigidity and steric bulk remain. In particular, the full width at half maximum (FWHM) of the photoluminescence spectrum in toluene of (1,7)tBuCzpPhTrz is reduced by 34% and blue-shifted by 20 nm compared to that of (1,4)tBuCzpPhTrz. In doped films, the compounds reach high photoluminescence quantum yields (ΦPL) of 91 and 81%, respectively. The chiroptical properties reveal dissymmetry factors |gPL| of up to 5 ? 10?4. These results demonstrate the impact of the cyclophane for the development of CP-TADF materials and add to the currently limited scope of available planar chiral donors.
Citation
Seibert , J , Xu , Y , Hafeez , H , Podlech , J , Favereau , L , Spuling , E , Waldhelm , C , Nieger , M , Fuhr , O , Hassan , Z , Crassous , J , Samuel , I D W , Zysman-Colman , E & Bräse , S 2024 , ' A novel carbazolophane : a comparison of the performance of two planar chiral CP-TADF emitters ' , Advanced Functional Materials , vol. EarlyView . https://doi.org/10.1002/adfm.202401956
Publication
Advanced Functional Materials
Status
Peer reviewed
ISSN
1616-301XType
Journal article
Description
Jürgen Manchot Foundation Deutsche Forschungsgemeinschaft. Grant Number: EXC-2082/1–390761711 China Scholarship Council. Grant Number: 202106310038 Engineering and Physical Sciences Research Council. Grant Numbers: EP/R035164/1, EP/W015137/1, EP/W524505/1 Helmholtz Association Program Ministère de l’Enseignement Supérieur et de la Recherche Centre National de la Recherche ScientifiqueCollections
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