Synthesis, structures and fluorescence properties of gem -linked cyclic tetraphenylethylenes and cyclic hexaphenylethylenes
Rigid cyclic molecules are of great interest due to their intriguing structures and unique properties. Here, we report the facile synthesis of gem -linked cyclic tetraphenylethylenes and cyclic hexaphenylethylenes, namely [n]CTPEs and [n]CHPEs, via the Pt-mediated cyclization of diborylated tetraphe...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2022-05, Vol.9 (11), p.2932-2938 |
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| container_title | Organic Chemistry Frontiers |
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| creator | He, Huowang Li, Jian-An Zhang, Yihuan Idrees, Sumra Cai, Jin Li, Yongying Osuka, Atsuhiro Xu, Bingjia Jiang, Hua-Wei |
| description | Rigid cyclic molecules are of great interest due to their intriguing structures and unique properties. Here, we report the facile synthesis of
gem
-linked cyclic tetraphenylethylenes and cyclic hexaphenylethylenes, namely [n]CTPEs and [n]CHPEs,
via
the Pt-mediated cyclization of diborylated tetraphenylethylene (TPE) derivatives and subsequent reductive elimination. The structure of [2]CTPE was revealed by X-ray single crystal analysis. The structures and the ring strain energies of all [n]CTPEs and [n]CHPEs obtained were calculated and compared with those of [
n
]cycloparaphenylenes. Most of the macrocycles showed enhanced aggregation-induced emission (AIE), which was comparable to that of the TPE monomer. By contrast, [2]CTPE exhibits distinctive dual-state emission properties and a long solid-state fluorescence lifetime, which may result from its highly strained rigid structure. This work provides a new direction for organic luminogens with prominent AIE characteristics and dual-state emission. |
| doi_str_mv | 10.1039/D2QO00395C |
| format | Article |
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gem
-linked cyclic tetraphenylethylenes and cyclic hexaphenylethylenes, namely [n]CTPEs and [n]CHPEs,
via
the Pt-mediated cyclization of diborylated tetraphenylethylene (TPE) derivatives and subsequent reductive elimination. The structure of [2]CTPE was revealed by X-ray single crystal analysis. The structures and the ring strain energies of all [n]CTPEs and [n]CHPEs obtained were calculated and compared with those of [
n
]cycloparaphenylenes. Most of the macrocycles showed enhanced aggregation-induced emission (AIE), which was comparable to that of the TPE monomer. By contrast, [2]CTPE exhibits distinctive dual-state emission properties and a long solid-state fluorescence lifetime, which may result from its highly strained rigid structure. This work provides a new direction for organic luminogens with prominent AIE characteristics and dual-state emission.</description><identifier>ISSN: 2052-4129</identifier><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4129</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/D2QO00395C</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Crystal structure ; Emission ; Fluorescence ; Organic chemistry ; Rigid structures ; Single crystals ; Synthesis</subject><ispartof>Organic Chemistry Frontiers, 2022-05, Vol.9 (11), p.2932-2938</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c259t-87a3def0737a13aaa647f088d487c09969ab30e2afccb0450b7f5c9b237ce4c53</citedby><cites>FETCH-LOGICAL-c259t-87a3def0737a13aaa647f088d487c09969ab30e2afccb0450b7f5c9b237ce4c53</cites><orcidid>0000-0001-6580-3240 ; 0000-0001-8970-3770</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids></links><search><creatorcontrib>He, Huowang</creatorcontrib><creatorcontrib>Li, Jian-An</creatorcontrib><creatorcontrib>Zhang, Yihuan</creatorcontrib><creatorcontrib>Idrees, Sumra</creatorcontrib><creatorcontrib>Cai, Jin</creatorcontrib><creatorcontrib>Li, Yongying</creatorcontrib><creatorcontrib>Osuka, Atsuhiro</creatorcontrib><creatorcontrib>Xu, Bingjia</creatorcontrib><creatorcontrib>Jiang, Hua-Wei</creatorcontrib><title>Synthesis, structures and fluorescence properties of gem -linked cyclic tetraphenylethylenes and cyclic hexaphenylethylenes</title><title>Organic Chemistry Frontiers</title><description>Rigid cyclic molecules are of great interest due to their intriguing structures and unique properties. Here, we report the facile synthesis of
gem
-linked cyclic tetraphenylethylenes and cyclic hexaphenylethylenes, namely [n]CTPEs and [n]CHPEs,
via
the Pt-mediated cyclization of diborylated tetraphenylethylene (TPE) derivatives and subsequent reductive elimination. The structure of [2]CTPE was revealed by X-ray single crystal analysis. The structures and the ring strain energies of all [n]CTPEs and [n]CHPEs obtained were calculated and compared with those of [
n
]cycloparaphenylenes. Most of the macrocycles showed enhanced aggregation-induced emission (AIE), which was comparable to that of the TPE monomer. By contrast, [2]CTPE exhibits distinctive dual-state emission properties and a long solid-state fluorescence lifetime, which may result from its highly strained rigid structure. This work provides a new direction for organic luminogens with prominent AIE characteristics and dual-state emission.</description><subject>Crystal structure</subject><subject>Emission</subject><subject>Fluorescence</subject><subject>Organic chemistry</subject><subject>Rigid structures</subject><subject>Single crystals</subject><subject>Synthesis</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpdkE9LxDAQxYMouKx78RMEvInVadI0zVHWv7CwiHouaTqxXbttTVKw-OWt7ILiZebB7_GGeYScxnAZA1dXN-xpDZMQywMyYyBYlMRMHf7Rx2Th_QYAYiZSEHJGvp7HNlToa39BfXCDCYNDT3VbUtsM3aQNtgZp77oeXagn1ln6hlsaNXX7jiU1o2lqQwMGp_sK27HBUE2j3cfseYWf__EJObK68bjY7zl5vbt9WT5Eq_X94_J6FRkmVIgyqXmJFiSXOuZa6zSRFrKsTDJpQKlU6YIDMm2NKSARUEgrjCoYlwYTI_icnO1ypyc-BvQh33SDa6eTOUtlLEFxBpPrfOcyrvPeoc17V2-1G_MY8p9-899--TeI-3Bf</recordid><startdate>20220531</startdate><enddate>20220531</enddate><creator>He, Huowang</creator><creator>Li, Jian-An</creator><creator>Zhang, Yihuan</creator><creator>Idrees, Sumra</creator><creator>Cai, Jin</creator><creator>Li, Yongying</creator><creator>Osuka, Atsuhiro</creator><creator>Xu, Bingjia</creator><creator>Jiang, Hua-Wei</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0001-6580-3240</orcidid><orcidid>https://orcid.org/0000-0001-8970-3770</orcidid></search><sort><creationdate>20220531</creationdate><title>Synthesis, structures and fluorescence properties of gem -linked cyclic tetraphenylethylenes and cyclic hexaphenylethylenes</title><author>He, Huowang ; Li, Jian-An ; Zhang, Yihuan ; Idrees, Sumra ; Cai, Jin ; Li, Yongying ; Osuka, Atsuhiro ; Xu, Bingjia ; Jiang, Hua-Wei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c259t-87a3def0737a13aaa647f088d487c09969ab30e2afccb0450b7f5c9b237ce4c53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Crystal structure</topic><topic>Emission</topic><topic>Fluorescence</topic><topic>Organic chemistry</topic><topic>Rigid structures</topic><topic>Single crystals</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>He, Huowang</creatorcontrib><creatorcontrib>Li, Jian-An</creatorcontrib><creatorcontrib>Zhang, Yihuan</creatorcontrib><creatorcontrib>Idrees, Sumra</creatorcontrib><creatorcontrib>Cai, Jin</creatorcontrib><creatorcontrib>Li, Yongying</creatorcontrib><creatorcontrib>Osuka, Atsuhiro</creatorcontrib><creatorcontrib>Xu, Bingjia</creatorcontrib><creatorcontrib>Jiang, Hua-Wei</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic Chemistry Frontiers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>He, Huowang</au><au>Li, Jian-An</au><au>Zhang, Yihuan</au><au>Idrees, Sumra</au><au>Cai, Jin</au><au>Li, Yongying</au><au>Osuka, Atsuhiro</au><au>Xu, Bingjia</au><au>Jiang, Hua-Wei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, structures and fluorescence properties of gem -linked cyclic tetraphenylethylenes and cyclic hexaphenylethylenes</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2022-05-31</date><risdate>2022</risdate><volume>9</volume><issue>11</issue><spage>2932</spage><epage>2938</epage><pages>2932-2938</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>Rigid cyclic molecules are of great interest due to their intriguing structures and unique properties. Here, we report the facile synthesis of
gem
-linked cyclic tetraphenylethylenes and cyclic hexaphenylethylenes, namely [n]CTPEs and [n]CHPEs,
via
the Pt-mediated cyclization of diborylated tetraphenylethylene (TPE) derivatives and subsequent reductive elimination. The structure of [2]CTPE was revealed by X-ray single crystal analysis. The structures and the ring strain energies of all [n]CTPEs and [n]CHPEs obtained were calculated and compared with those of [
n
]cycloparaphenylenes. Most of the macrocycles showed enhanced aggregation-induced emission (AIE), which was comparable to that of the TPE monomer. By contrast, [2]CTPE exhibits distinctive dual-state emission properties and a long solid-state fluorescence lifetime, which may result from its highly strained rigid structure. This work provides a new direction for organic luminogens with prominent AIE characteristics and dual-state emission.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D2QO00395C</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-6580-3240</orcidid><orcidid>https://orcid.org/0000-0001-8970-3770</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2052-4129 |
| ispartof | Organic Chemistry Frontiers, 2022-05, Vol.9 (11), p.2932-2938 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Crystal structure Emission Fluorescence Organic chemistry Rigid structures Single crystals Synthesis |
| title | Synthesis, structures and fluorescence properties of gem -linked cyclic tetraphenylethylenes and cyclic hexaphenylethylenes |
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