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Regulating the dimensionality of diphosphaperylenediimide-based polymers by coordinating the out-of-plane anisotropic π-framework toward Ag+

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Abstract

The development of hetero-π-conjugated molecules is of significance for constructing diverse assembling superstructures based on heteroatom-related bonded or nonbonded interactions. Herein, we developed one-pot P-heteroannulation via palladium-catalyzed dual P—C bonds formation and subsequent sulfidation to construct two isomeric diphosphaperylenediimides (cis-5 and trans-5). The unique out-of-plane anisotropic π-framework induced a cumulative anisotropy with a dipole moment of up to 8.82 D for cis-5, leading to distinct supramolecular packing arrangements. Optical and electrochemical characterizations demonstrated that they showed the largest redshifts extending to 574 nm and rather low-lying LUMO levels of −4.41 eV. Furthermore, the introduced P=S moieties endowed these diphosphaperylenediimides with prominent coordination ability towards Ag+, thus the first example of perylene diimide (PDI) core-involved metal-organic coordination polymers (MOCPs) with tunable dimensionality varied from 1D, 2D, to 3D were tactfully achieved. In view of easy accessibility and 2D layered porous structure, thus 2D (trans-5)·(AgOTf) based MOCP showed high crystallinity and good CO2 adsorption capacity with surface area of 112 m2/g. The result opens a span-new avenue for exploring rylene imide-based MOCPs and related properties by integrating P functionality.

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Acknowledgements

This work was supported by Shandong Provincial Natural Science Foundation (ZR2019ZD50), the National Natural Science Foundation of China (22005107, 21790361, 22122503), and the China Postdoctoral Science Foundation (2020M682693).

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Authors and Affiliations

  1. Key Laboratory of Organic Optoelectronics and Molecular Engineering, Department of Chemistry, Tsinghua University, Beijing, 100084, China

    Zetong Ma, Yujian Liu, Zhaohui Wang & Wei Jiang

  2. Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640, China

    Zetong Ma, Shengdong Wang & Jiadong Zhou

Authors
  1. Zetong Ma
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  2. Yujian Liu
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  3. Shengdong Wang
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  4. Jiadong Zhou
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  5. Zhaohui Wang
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  6. Wei Jiang
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Correspondence to Wei Jiang.

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Supporting information 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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Regulating the dimensionality of diphosphaperylenediimide-based polymers by coordinating the out-of-plane anisotropic π-framework toward Ag+

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Ma, Z., Liu, Y., Wang, S. et al. Regulating the dimensionality of diphosphaperylenediimide-based polymers by coordinating the out-of-plane anisotropic π-framework toward Ag+. Sci. China Chem. 65, 1741–1748 (2022). https://doi.org/10.1007/s11426-022-1325-1

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  • DOI: https://doi.org/10.1007/s11426-022-1325-1

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