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Chiroluminophores based on non-conjugated benzenes

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Abstract

Point-chiral groups as pendants conjugated to the aromatic luminophore generate weak chiroptical signals without self-assembly, showing the dependence on the flexibility of tethers, which hinders the development of point-chiral molecular materials with chiroptical properties such as the circularly polarized luminescence (CPL). Herein we introduce the molecular chiroptical materials based on the point chirality on a single benzene luminophore scaffold. Substitutes were stepwise conjugated to single benzene luminophores to boost the steric hindrance and tension, whereby the chirality transfer efficiency from point-chiral substituents to luminophores was enhanced. Multiple intramolecular CH−π interactions anchor the whole asymmetric geometry with ultra-high rotation energy barriers and excellent thermostability. Dissymmetry g-factors of circular dichroism and CPL spectra up to 10−3 order of magnitude were realized in solutions, which are comparable to the inherent-chiral luminophores such as helicene and binaphthyl derivatives. The acridine-appended single benzene system shows the emergence of thermally activated delayed fluorescence (TADF), which extends the potentials of the single benzene chiral system in the TADF-based chiroptical devices.

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Acknowledgements

This work is also supported by the National Natural Science Foundation of China (21901145, 22171165). We also acknowledge the financial support from Youth cross-scientific innovation group of Shandong University (2020QNQT003) and the project of construction and management research of laboratory of Shandong University (sy20202202). We thank Prof. Di Sun at Shandong University for assistance with the data collection of X-ray crystal structures.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, China

    Yiping Liu, Aiyou Hao & Pengyao Xing

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  1. Yiping Liu
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  2. Aiyou Hao
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  3. Pengyao Xing
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Correspondence to Pengyao Xing.

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The authors declare no conflict of interest.

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The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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Liu, Y., Hao, A. & Xing, P. Chiroluminophores based on non-conjugated benzenes. Sci. China Chem. 66, 2130–2140 (2023). https://doi.org/10.1007/s11426-023-1630-5

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  • DOI: https://doi.org/10.1007/s11426-023-1630-5

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