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Synthesis and macrocyclization-induced emission enhancement of benzothiadiazole-based macrocycle

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  • Shuo Li

    (Shanghai University)

  • Kun Liu

    (Tianjin Normal University)

  • Xue-Chen Feng

    (Tianjin Normal University)

  • Zhao-Xian Li

    (Tianjin Normal University)

  • Zhi-Yuan Zhang

    (Tianjin Normal University)

  • Bin Wang

    (Tianjin Normal University)

  • Minjie Li

    (Shanghai University)

  • Yue-Ling Bai

    (Shanghai University)

  • Lei Cui

    (Shanghai University)

  • Chunju Li

    (Shanghai University
    Tianjin Normal University)

Abstract

We presented an effective and universal strategy for the improvement of luminophore’s solid-state emission, i.e., macrocyclization-induced emission enhancement (MIEE), by linking luminophores through C(sp3) bridges to give a macrocycle. Benzothiadiazole-based macrocycle (BT-LC) has been synthesized by a one-step condensation of the monomer 4,7-bis(2,4-dimethoxyphenyl)−2,1,3-benzothiadiazole (BT-M) with paraformaldehyde, catalyzed by Lewis acid. In comparison with the monomer, macrocycle BT-LC produces much more intense fluorescence in the solid state (ΦPL = 99%) and exhibits better device performance in the application of OLEDs. Single-crystal analysis and theoretical simulations reveal that the monomer can return to the ground state through a minimum energy crossing point (MECPS1/S0), resulting in the decrease of fluorescence efficiency. For the macrocycle, its inherent structural rigidity prohibits this non-radiative relaxation process and promotes the radiative relaxation, therefore emitting intense fluorescence. More significantly, MIEE strategy has good universality that several macrocycles with different luminophores also display emission improvement.

Suggested Citation

  • Shuo Li & Kun Liu & Xue-Chen Feng & Zhao-Xian Li & Zhi-Yuan Zhang & Bin Wang & Minjie Li & Yue-Ling Bai & Lei Cui & Chunju Li, 2022. "Synthesis and macrocyclization-induced emission enhancement of benzothiadiazole-based macrocycle," Nature Communications, Nature, vol. 13(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30121-0
    DOI: 10.1038/s41467-022-30121-0
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    1. Huimin Ding & Jian Li & Guohua Xie & Guiqing Lin & Rufan Chen & Zhengkang Peng & Chuluo Yang & Baoshan Wang & Junliang Sun & Cheng Wang, 2018. "An AIEgen-based 3D covalent organic framework for white light-emitting diodes," Nature Communications, Nature, vol. 9(1), pages 1-7, December.
    2. Jinyang Zhao & Yongli Yan & Zhenhua Gao & Yuxiang Du & Haiyun Dong & Jiannian Yao & Yong Sheng Zhao, 2019. "Full-color laser displays based on organic printed microlaser arrays," Nature Communications, Nature, vol. 10(1), pages 1-7, December.
    3. R. H. Friend & R. W. Gymer & A. B. Holmes & J. H. Burroughes & R. N. Marks & C. Taliani & D. D. C. Bradley & D. A. Dos Santos & J. L. Brédas & M. Lögdlund & W. R. Salaneck, 1999. "Electroluminescence in conjugated polymers," Nature, Nature, vol. 397(6715), pages 121-128, January.
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    1. Ying Wei & Chunxiao Zhong & Yue Sun & Shuwei Ma & Mingjian Ni & Xiangping Wu & Yongxia Yan & Lei Yang & Ilya A. Khodov & Jiaoyang Ge & Yang Li & Dongqing Lin & Yongxia Wang & Qiujing Bao & He Zhang & , 2024. "C-H-activated Csp2-Csp3 diastereoselective gridization enables ultraviolet-emitting stereo-molecular nanohydrocarbons with mulitple H···H interactions," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    2. Sha Bai & Lu-Wen Zhang & Zi-Hang Wei & Fang Wang & Qing-Wen Zhu & Ying-Feng Han, 2024. "Calix[2]azolium[2]benzimidazolone hosts for selective binding of neutral substrates in water," Nature Communications, Nature, vol. 15(1), pages 1-10, December.

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