Redox-Active Dihydrophenazine-Based Macrocycle: Synthesis, Conformation-Adaptive Behavior and Host-Guest Complexation with Tetracyanoquinodimethane
Qiong-Yan Hong
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062 China
Search for more papers by this authorBin Huang
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062 China
Search for more papers by this authorMeng-Xiang Wu
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062 China
Search for more papers by this authorLin Xu
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062 China
Search for more papers by this authorXiao-Li Zhao
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062 China
Search for more papers by this authorXueliang Shi
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062 China
Search for more papers by this authorCorresponding Author
Hai-Bo Yang
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062 China
E-mail: [email protected]Search for more papers by this authorQiong-Yan Hong
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062 China
Search for more papers by this authorBin Huang
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062 China
Search for more papers by this authorMeng-Xiang Wu
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062 China
Search for more papers by this authorLin Xu
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062 China
Search for more papers by this authorXiao-Li Zhao
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062 China
Search for more papers by this authorXueliang Shi
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062 China
Search for more papers by this authorCorresponding Author
Hai-Bo Yang
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062 China
E-mail: [email protected]Search for more papers by this authorComprehensive Summary
A novel macrocycle based on conformation-adaptive and electron-rich dihydrophenazine was designed and synthesized. On the one hand, the macrocycle showed host-guest interactions with tetracyanoquinodimethane (TCNQ) driving by charge transfer interaction between them. Meanwhile, host-guest complexation was accompanied by fluorescence quenching and conformational change of the macrocycle. On the other hand, the oxidation of the macrocycle resulted in its diradical cation analogue and induced the release of the guest molecule TCNQ, thereby accomplishing reversible binding dynamics. Therefore, this work well illustrates the chemical and structural versatility of dihydrophenazine in the synthesis of macrocycles and their host-guest chemistry.
Supporting Information
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Appendix S1: Supporting information |
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