Synthesis and Characterization of Two [2]Catenanes Based on Phenylene-diacetylene Crown Ethers
Two charged donor-acceptor [2]catenanes were synthesized by the cyclization of the π-acceptor 1,1 ＇-[1, 4-phenylenebis-（methylene）]bis（4,4＇-bipyridinium）bis（hexafluorophosphate）（2） and bis（bromomethyl）benzene with the templates of the π-donor phenylene-diacetylene crown ethers la and lb in the yield...
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| Veröffentlicht in: | Chemical research in Chinese universities 2013-12, Vol.29 (6), p.1094-1097 |
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| creator | Chen, Mu-juan Zhou, Song-gen Li, Mei Lei, Chun-yan Xiao, Rui Jiang, La-sheng |
| description | Two charged donor-acceptor [2]catenanes were synthesized by the cyclization of the π-acceptor 1,1 ＇-[1, 4-phenylenebis-（methylene）]bis（4,4＇-bipyridinium）bis（hexafluorophosphate）（2） and bis（bromomethyl）benzene with the templates of the π-donor phenylene-diacetylene crown ethers la and lb in the yields of 31%, 35%, respectively. The mass spectra, 1H and 13C NMR spectra confirm that the phenylene-diacetylene crown ethers, with a nonaromatic ~r-system, successfully template the cyclization of CBPQT4＋. The X-ray crystallography analysis shows that the CBPQT4＋ ring encircles around the phenylene motif of the crown ethers, leaving the 1,3-butadiyne fragment out of the cavity of CBPQT4＋ ring. The mechanically interlocked structure of [2]catenanes was stabilized by the cooperative effects of π-stacking and hydrogen bonding interactions. |
| doi_str_mv | 10.1007/s40242-013-3218-0 |
| format | Article |
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The mass spectra, 1H and 13C NMR spectra confirm that the phenylene-diacetylene crown ethers, with a nonaromatic ~r-system, successfully template the cyclization of CBPQT4＋. The X-ray crystallography analysis shows that the CBPQT4＋ ring encircles around the phenylene motif of the crown ethers, leaving the 1,3-butadiyne fragment out of the cavity of CBPQT4＋ ring. The mechanically interlocked structure of [2]catenanes was stabilized by the cooperative effects of π-stacking and hydrogen bonding interactions.</description><identifier>ISSN: 1005-9040</identifier><identifier>EISSN: 2210-3171</identifier><identifier>DOI: 10.1007/s40242-013-3218-0</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Analytical Chemistry ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Inorganic Chemistry ; Organic Chemistry ; Physical Chemistry ; 二乙炔 ; 亚苯基 ; 冠醚 ; 合成 ; 氢键相互作用 ; 环化反应 ; 索烃 ; 表征</subject><ispartof>Chemical research in Chinese universities, 2013-12, Vol.29 (6), p.1094-1097</ispartof><rights>Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH 2013</rights><rights>Copyright © Wanfang Data Co. Ltd. All Rights Reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c300t-6d8b9d5e022a10def1dd87e8c9e03333ded95063917b4e11c311bcbbdbec348d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Uhttp://image.cqvip.com/vip1000/qk/86071X/86071X.jpg</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s40242-013-3218-0$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s40242-013-3218-0$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids></links><search><creatorcontrib>Chen, Mu-juan</creatorcontrib><creatorcontrib>Zhou, Song-gen</creatorcontrib><creatorcontrib>Li, Mei</creatorcontrib><creatorcontrib>Lei, Chun-yan</creatorcontrib><creatorcontrib>Xiao, Rui</creatorcontrib><creatorcontrib>Jiang, La-sheng</creatorcontrib><title>Synthesis and Characterization of Two [2]Catenanes Based on Phenylene-diacetylene Crown Ethers</title><title>Chemical research in Chinese universities</title><addtitle>Chem. Res. Chin. Univ</addtitle><addtitle>Chemical Research in Chinese University</addtitle><description>Two charged donor-acceptor [2]catenanes were synthesized by the cyclization of the π-acceptor 1,1 ＇-[1, 4-phenylenebis-（methylene）]bis（4,4＇-bipyridinium）bis（hexafluorophosphate）（2） and bis（bromomethyl）benzene with the templates of the π-donor phenylene-diacetylene crown ethers la and lb in the yields of 31%, 35%, respectively. The mass spectra, 1H and 13C NMR spectra confirm that the phenylene-diacetylene crown ethers, with a nonaromatic ~r-system, successfully template the cyclization of CBPQT4＋. The X-ray crystallography analysis shows that the CBPQT4＋ ring encircles around the phenylene motif of the crown ethers, leaving the 1,3-butadiyne fragment out of the cavity of CBPQT4＋ ring. The mechanically interlocked structure of [2]catenanes was stabilized by the cooperative effects of π-stacking and hydrogen bonding interactions.</description><subject>Analytical Chemistry</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Inorganic Chemistry</subject><subject>Organic Chemistry</subject><subject>Physical Chemistry</subject><subject>二乙炔</subject><subject>亚苯基</subject><subject>冠醚</subject><subject>合成</subject><subject>氢键相互作用</subject><subject>环化反应</subject><subject>索烃</subject><subject>表征</subject><issn>1005-9040</issn><issn>2210-3171</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp9kEtLBDEQhIMouD5-gLd49BDtTuZ51MEXCArqSTRkJj07s2hGk5Hd9dcbXdGbfemGrq8KirE9hEMEyI9CAjKRAlAJJbEQsMYmUiIIhTmus0kUpaKEBDbZVggzAFVmWTJhT7dLN3YU-sCNs7zqjDfNSL7_MGM_OD60_G4-8Af5WJmRnHEU-IkJZHl83nTkls_kSNjeNDR-37zyw9zx0-jqww7baM1zoN2fvc3uz07vqgtxdX1-WR1fiUYBjCKzRV3alEBKg2CpRWuLnIqmJFBxLNkyhUyVmNcJITYKsW7q2tbUqKSwapsdrHznxrXGTfVsePcuJuqpXSy6xXImYzWQAaZRiytt44cQPLX61fcvxi81gv4qU6_K1JHQX2VqiIxcMSFq3ZT8X8B_0P5PUDe46VvkfpOSApI0K3P1CTM1g20</recordid><startdate>20131201</startdate><enddate>20131201</enddate><creator>Chen, Mu-juan</creator><creator>Zhou, Song-gen</creator><creator>Li, Mei</creator><creator>Lei, Chun-yan</creator><creator>Xiao, Rui</creator><creator>Jiang, La-sheng</creator><general>Springer Berlin Heidelberg</general><general>School of Chemistry and Environment, South China Normal University, Guangzhou 510006, P.R.China</general><scope>2RA</scope><scope>92L</scope><scope>CQIGP</scope><scope>~WA</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>2B.</scope><scope>4A8</scope><scope>92I</scope><scope>93N</scope><scope>PSX</scope><scope>TCJ</scope></search><sort><creationdate>20131201</creationdate><title>Synthesis and Characterization of Two [2]Catenanes Based on Phenylene-diacetylene Crown Ethers</title><author>Chen, Mu-juan ; Zhou, Song-gen ; Li, Mei ; Lei, Chun-yan ; Xiao, Rui ; Jiang, La-sheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c300t-6d8b9d5e022a10def1dd87e8c9e03333ded95063917b4e11c311bcbbdbec348d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Analytical Chemistry</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Inorganic Chemistry</topic><topic>Organic Chemistry</topic><topic>Physical Chemistry</topic><topic>二乙炔</topic><topic>亚苯基</topic><topic>冠醚</topic><topic>合成</topic><topic>氢键相互作用</topic><topic>环化反应</topic><topic>索烃</topic><topic>表征</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Mu-juan</creatorcontrib><creatorcontrib>Zhou, Song-gen</creatorcontrib><creatorcontrib>Li, Mei</creatorcontrib><creatorcontrib>Lei, Chun-yan</creatorcontrib><creatorcontrib>Xiao, Rui</creatorcontrib><creatorcontrib>Jiang, La-sheng</creatorcontrib><collection>中文科技期刊数据库</collection><collection>中文科技期刊数据库-CALIS站点</collection><collection>中文科技期刊数据库-7.0平台</collection><collection>中文科技期刊数据库- 镜像站点</collection><collection>CrossRef</collection><collection>Wanfang Data Journals - Hong Kong</collection><collection>WANFANG Data Centre</collection><collection>Wanfang Data Journals</collection><collection>万方数据期刊 - 香港版</collection><collection>China Online Journals (COJ)</collection><collection>China Online Journals (COJ)</collection><jtitle>Chemical research in Chinese universities</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Mu-juan</au><au>Zhou, Song-gen</au><au>Li, Mei</au><au>Lei, Chun-yan</au><au>Xiao, Rui</au><au>Jiang, La-sheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Characterization of Two [2]Catenanes Based on Phenylene-diacetylene Crown Ethers</atitle><jtitle>Chemical research in Chinese universities</jtitle><stitle>Chem. Res. Chin. Univ</stitle><addtitle>Chemical Research in Chinese University</addtitle><date>2013-12-01</date><risdate>2013</risdate><volume>29</volume><issue>6</issue><spage>1094</spage><epage>1097</epage><pages>1094-1097</pages><issn>1005-9040</issn><eissn>2210-3171</eissn><abstract>Two charged donor-acceptor [2]catenanes were synthesized by the cyclization of the π-acceptor 1,1 ＇-[1, 4-phenylenebis-（methylene）]bis（4,4＇-bipyridinium）bis（hexafluorophosphate）（2） and bis（bromomethyl）benzene with the templates of the π-donor phenylene-diacetylene crown ethers la and lb in the yields of 31%, 35%, respectively. The mass spectra, 1H and 13C NMR spectra confirm that the phenylene-diacetylene crown ethers, with a nonaromatic ~r-system, successfully template the cyclization of CBPQT4＋. The X-ray crystallography analysis shows that the CBPQT4＋ ring encircles around the phenylene motif of the crown ethers, leaving the 1,3-butadiyne fragment out of the cavity of CBPQT4＋ ring. 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| subjects | Analytical Chemistry Chemistry Chemistry and Materials Science Chemistry/Food Science Inorganic Chemistry Organic Chemistry Physical Chemistry 二乙炔 亚苯基 冠醚 合成 氢键相互作用 环化反应 索烃 表征 |
| title | Synthesis and Characterization of Two [2]Catenanes Based on Phenylene-diacetylene Crown Ethers |
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