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Three-dimensional conjugated macrocycle with large polyaromatic blocks constructed by post-π-extension

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Abstract

Generally, the conjugated homo-macrocycles (CHMs) are synthesized by covalently linking the repeating subunits. However, large subunits are often difficult to conjugate together due to severe stereo-hindrance. Meanwhile, large polyaromatic blocks can not only incorporate its appealing electronic and optical properties into CHMs but also distort the CHMs from planar to three-dimensional (3D) molecular structure. Here we synthesized the 3D CHM composed of large polyaromatic units by post-π-extension. Specifically, cyclo-m-phenylenes, as the cyclic precursor, were π-extended by C-C coupling and then subjected to dehydrocyclization, affording cyclo-1,3-dibenzo[e,1]pyrenylenes (CMDP). The structures of CMDPs were unambiguously characterized by single crystal X-ray diffraction, showing a congested and strained 3D conformation, which was also confirmed by theoretical calculations. Compared with the monomer, CMDPs showed redshifted absorption and emission, as well as a tenfold enhancement in photoluminescence quantum yield, which could be attributed to their 3D conformation.

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Acknowledgements

This work was supported by the Ministry of Science and Technology of China (2017YFA0204902, 2018YFA0209500), the National Natural Science Foundation of China (21771155, 21721001) and the Fundamental Research Funds for the Central Universities (20720180035).

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Authors and Affiliations

  1. State Key Laboratory for Physical Chemistry of Solid Surfaces, Collaborative Innovation Center of Chemistry for Energy Materials, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China

    Shun-He Liu, Hao Hou, Ze-Ying Deng, Xin-Rong Wang, Chun Tang, Yang-Yang Ju, Liu-Bin Feng & Yuan-Zhi Tan

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  1. Shun-He Liu
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  2. Hao Hou
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  3. Ze-Ying Deng
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Correspondence to Yuan-Zhi Tan.

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11426_2020_9806_MOESM1_ESM.pdf

Supporting Information for Three-dimensional Conjugated Macrocycle with Large Polyaromatic Blocks Constructed by Post-π-Extension

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Liu, SH., Hou, H., Deng, ZY. et al. Three-dimensional conjugated macrocycle with large polyaromatic blocks constructed by post-π-extension. Sci. China Chem. 63, 1626–1631 (2020). https://doi.org/10.1007/s11426-020-9806-8

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