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

Shuo Li, Kun Liu, Xue-Chen Feng, Zhao-Xian Li, Zhi-Yuan Zhang, Bin Wang, Minjie Li, Yue-Ling Bai (), Lei Cui () and Chunju Li ()
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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

Nature Communications, 2022, vol. 13, issue 1, 1-7

Abstract: 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.

Date: 2022
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DOI: 10.1038/s41467-022-30121-0

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