Redox‐Active Dihydrophenazine‐Based Macrocycle: Synthesis, Conformation‐Adaptive Behavior and Host‐Guest Complexation with Tetracyanoquinodimethane
Comprehensive 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,...
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| Veröffentlicht in: | Chinese journal of chemistry 2024-08, Vol.42 (16), p.1895-1900 |
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| container_end_page | 1900 |
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| container_issue | 16 |
| container_start_page | 1895 |
| container_title | Chinese journal of chemistry |
| container_volume | 42 |
| creator | Hong, Qiong‐Yan Huang, Bin Wu, Meng‐Xiang Xu, Lin Zhao, Xiao‐Li Shi, Xueliang Yang, Hai‐Bo |
| description | Comprehensive 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.
A novel macrocycle based on conformation‐adaptive and electron‐rich dihydrophenazine was designed and synthesized, and its host‐guest properties and radical cation species were investigated. The resultant macrocycle could bind electron‐deficient guest TCNQ to form a host‐guest complex, and the oxidation of the macrocycle generated a stable diradical cation and induced the release of the guest molecule. |
| doi_str_mv | 10.1002/cjoc.202400134 |
| format | Article |
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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.
A novel macrocycle based on conformation‐adaptive and electron‐rich dihydrophenazine was designed and synthesized, and its host‐guest properties and radical cation species were investigated. The resultant macrocycle could bind electron‐deficient guest TCNQ to form a host‐guest complex, and the oxidation of the macrocycle generated a stable diradical cation and induced the release of the guest molecule.</description><identifier>ISSN: 1001-604X</identifier><identifier>EISSN: 1614-7065</identifier><identifier>DOI: 10.1002/cjoc.202400134</identifier><language>eng</language><publisher>Weinheim: WILEY‐VCH Verlag GmbH & Co. KGaA</publisher><subject>Charge transfer ; Charge transfer interaction ; Chemical synthesis ; Complexation ; Conformation ; Conformational adaptation ; Dihydrophenazine ; Host‐guest interactions ; Macrocycle ; Organic radical ; Oxidation ; Redox‐active ; Supramolecular chemistry ; Tetracyanoquinodimethane</subject><ispartof>Chinese journal of chemistry, 2024-08, Vol.42 (16), p.1895-1900</ispartof><rights>2024 SIOC, CAS, Shanghai, & WILEY‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c2724-414562322e1884908e04d0a6a6a70a8610f18547e3275ce151a1b1e7533d6b3d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcjoc.202400134$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcjoc.202400134$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27929,27930,45579,45580</link.rule.ids></links><search><creatorcontrib>Hong, Qiong‐Yan</creatorcontrib><creatorcontrib>Huang, Bin</creatorcontrib><creatorcontrib>Wu, Meng‐Xiang</creatorcontrib><creatorcontrib>Xu, Lin</creatorcontrib><creatorcontrib>Zhao, Xiao‐Li</creatorcontrib><creatorcontrib>Shi, Xueliang</creatorcontrib><creatorcontrib>Yang, Hai‐Bo</creatorcontrib><title>Redox‐Active Dihydrophenazine‐Based Macrocycle: Synthesis, Conformation‐Adaptive Behavior and Host‐Guest Complexation with Tetracyanoquinodimethane</title><title>Chinese journal of chemistry</title><description>Comprehensive 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.
A novel macrocycle based on conformation‐adaptive and electron‐rich dihydrophenazine was designed and synthesized, and its host‐guest properties and radical cation species were investigated. The resultant macrocycle could bind electron‐deficient guest TCNQ to form a host‐guest complex, and the oxidation of the macrocycle generated a stable diradical cation and induced the release of the guest molecule.</description><subject>Charge transfer</subject><subject>Charge transfer interaction</subject><subject>Chemical synthesis</subject><subject>Complexation</subject><subject>Conformation</subject><subject>Conformational adaptation</subject><subject>Dihydrophenazine</subject><subject>Host‐guest interactions</subject><subject>Macrocycle</subject><subject>Organic radical</subject><subject>Oxidation</subject><subject>Redox‐active</subject><subject>Supramolecular chemistry</subject><subject>Tetracyanoquinodimethane</subject><issn>1001-604X</issn><issn>1614-7065</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkb1OwzAUhSMEEuVnZY7ESortOHHKVgK0oCIkfiS2yNi3iqvEDnZaCBOPwM7b8SS4LYIRebiW7_mOr-4JggOM-hghcixmRvQJIhQhHNONoIdTTCOG0mTT3_1jlCL6uB3sODfzesZI2gs-b0Ga16_3j6Fo1QLCM1V20pqmBM3flAbfOeUOZHjNhTWiExWchHedbktwyh2FudFTY2veKqOXLpI3K59TKPlCGRtyLcOxca1vjubgWk_UTQWvKyJ8UW0Z3kNruei4Ns9zpY1UNbQl17AXbE155WD_p-4GDxfn9_k4mtyMLvPhJBKEERpRTJOUxIQAzjI6QBkgKhFP_WGIZylGU5wllEFMWCIAJ5jjJwwsiWOZPsUy3g0O176N9RP4GYuZmVvtvyxilCGSsWSQeVV_rfJ7cM7CtGisqrntCoyKZQDFMoDiNwAPDNbAi6qg-0dd5Fc3-R_7DTaLkJI</recordid><startdate>20240815</startdate><enddate>20240815</enddate><creator>Hong, Qiong‐Yan</creator><creator>Huang, Bin</creator><creator>Wu, Meng‐Xiang</creator><creator>Xu, Lin</creator><creator>Zhao, Xiao‐Li</creator><creator>Shi, Xueliang</creator><creator>Yang, Hai‐Bo</creator><general>WILEY‐VCH Verlag GmbH & Co. KGaA</general><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20240815</creationdate><title>Redox‐Active Dihydrophenazine‐Based Macrocycle: Synthesis, Conformation‐Adaptive Behavior and Host‐Guest Complexation with Tetracyanoquinodimethane</title><author>Hong, Qiong‐Yan ; Huang, Bin ; Wu, Meng‐Xiang ; Xu, Lin ; Zhao, Xiao‐Li ; Shi, Xueliang ; Yang, Hai‐Bo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2724-414562322e1884908e04d0a6a6a70a8610f18547e3275ce151a1b1e7533d6b3d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Charge transfer</topic><topic>Charge transfer interaction</topic><topic>Chemical synthesis</topic><topic>Complexation</topic><topic>Conformation</topic><topic>Conformational adaptation</topic><topic>Dihydrophenazine</topic><topic>Host‐guest interactions</topic><topic>Macrocycle</topic><topic>Organic radical</topic><topic>Oxidation</topic><topic>Redox‐active</topic><topic>Supramolecular chemistry</topic><topic>Tetracyanoquinodimethane</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hong, Qiong‐Yan</creatorcontrib><creatorcontrib>Huang, Bin</creatorcontrib><creatorcontrib>Wu, Meng‐Xiang</creatorcontrib><creatorcontrib>Xu, Lin</creatorcontrib><creatorcontrib>Zhao, Xiao‐Li</creatorcontrib><creatorcontrib>Shi, Xueliang</creatorcontrib><creatorcontrib>Yang, Hai‐Bo</creatorcontrib><collection>CrossRef</collection><jtitle>Chinese journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hong, Qiong‐Yan</au><au>Huang, Bin</au><au>Wu, Meng‐Xiang</au><au>Xu, Lin</au><au>Zhao, Xiao‐Li</au><au>Shi, Xueliang</au><au>Yang, Hai‐Bo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Redox‐Active Dihydrophenazine‐Based Macrocycle: Synthesis, Conformation‐Adaptive Behavior and Host‐Guest Complexation with Tetracyanoquinodimethane</atitle><jtitle>Chinese journal of chemistry</jtitle><date>2024-08-15</date><risdate>2024</risdate><volume>42</volume><issue>16</issue><spage>1895</spage><epage>1900</epage><pages>1895-1900</pages><issn>1001-604X</issn><eissn>1614-7065</eissn><abstract>Comprehensive 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.
A novel macrocycle based on conformation‐adaptive and electron‐rich dihydrophenazine was designed and synthesized, and its host‐guest properties and radical cation species were investigated. The resultant macrocycle could bind electron‐deficient guest TCNQ to form a host‐guest complex, and the oxidation of the macrocycle generated a stable diradical cation and induced the release of the guest molecule.</abstract><cop>Weinheim</cop><pub>WILEY‐VCH Verlag GmbH & Co. KGaA</pub><doi>10.1002/cjoc.202400134</doi><tpages>6</tpages></addata></record> |
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| subjects | Charge transfer Charge transfer interaction Chemical synthesis Complexation Conformation Conformational adaptation Dihydrophenazine Host‐guest interactions Macrocycle Organic radical Oxidation Redox‐active Supramolecular chemistry Tetracyanoquinodimethane |
| title | Redox‐Active Dihydrophenazine‐Based Macrocycle: Synthesis, Conformation‐Adaptive Behavior and Host‐Guest Complexation with Tetracyanoquinodimethane |
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