Axially chiral 1,4-dihydropyridine derivatives: aggregation-induced emission in exciplexes and application as viscosity probes
By combining the fluorophores of axially chiral 1,1′-binaphthol (BINOL) and 1,4-dihydropyridine derivatives, axially chiral 1,4-dihydropyridine derivatives (( R )-/( S )- 2 ) with aggregation-induced emission (AIE) in exciplexes were designed and synthesized. ( R )-/( S )- 2 emitted low fluorescence...
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| Veröffentlicht in: | RSC advances 2019-10, Vol.9 (55), p.32219-32225 |
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| container_title | RSC advances |
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| creator | Yang, Zeren Huo, Yanmin Liu, Yanke Du, Guifen Zhang, Wenhao Zhou, Lijie Zhan, Lihui Ren, Xuerui Duan, Wenzeng Gong, Shuwen |
| description | By combining the fluorophores of axially chiral 1,1′-binaphthol (BINOL) and 1,4-dihydropyridine derivatives, axially chiral 1,4-dihydropyridine derivatives ((
R
)-/(
S
)-
2
) with aggregation-induced emission (AIE) in exciplexes were designed and synthesized. (
R
)-/(
S
)-
2
emitted low fluorescence in THF solutions of their locally excited states; however, they emitted red-shifted fluorescence in the aggregate state upon exciplex formation. Moreover, (
R
)-/(
S
)-
2
showed linear and multi-exponential relationships between their local excited and exciplex fluorescence intensities and the viscosity of the medium, which allowed us to determine the viscosities of different mixed solvents. In addition, as an axially chiral viscosity probe, (
R
)-/(
S
)-
2
show excellent CD signals and have potential applications in the fields of chiral recognition and fluorescence imaging, which will broaden the new family of AIE fluorophores. To the best of our knowledge, there are few reports of axially chiral intramolecular exciplex-mediated AIE molecules.
Axially chiral 1,4-dihydropyridine derivatives ((
R
)-/(
S
)-
2
) with aggregation-induced emission (AIE) in exciplex were designed and synthesized. They have excellent CD signals and can determine the different viscosity in mixed solvents. |
| doi_str_mv | 10.1039/c9ra06553a |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_rsc_p</sourceid><recordid>TN_cdi_rsc_primary_c9ra06553a</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2661482687</sourcerecordid><originalsourceid>FETCH-LOGICAL-c494t-6e10a372b48ec50ef4e77337099867d8791d36b4896e907dcf2f464714afa5663</originalsourceid><addsrcrecordid>eNpdkttrFDEYxQex2FL74rsS8EXE0dwmmfRBWBYvhYIg-hyyyTe7KbPJmMwsOy_-7abdutbmJZfz4_AdTqrqBcHvCWbqg1XJYNE0zDypzijmoqZYqKcPzqfVRc43uCzRECrIs-qUFR63hJxVvxd7b_p-Rnbjk-kRecdr5zezS3GYk3c-AHKQ_M6Mfgf5Epn1OsG63GKofXCTBYdg63MuD8gHBHvrhx72kJEJDplh6L29w5HJaOezjdmPMxpSXEF-Xp10ps9wcb-fVz8_f_qx_Fpff_tytVxc15YrPtYCCDZM0hVvwTYYOg5SMiaxUq2QrpWKOCaKqgQoLJ3taMcFl4SbzjRCsPPq48F3mFZbcBbCWNLqIfmtSbOOxuv_leA3eh13urhRxXkxeHNvkOKvCfKoS2YLfW8CxClrKgThLRWtLOjrR-hNnFIo8TRlmFFCG8wK9fZA2RRzTtAdhyFY3zarl-r74q7ZRYFfPRz_iP7tsQAvD0DK9qj--xrsD_GUqiM</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2303212503</pqid></control><display><type>article</type><title>Axially chiral 1,4-dihydropyridine derivatives: aggregation-induced emission in exciplexes and application as viscosity probes</title><source>DOAJ Directory of Open Access Journals</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>PubMed Central Open Access</source><source>PubMed Central</source><creator>Yang, Zeren ; Huo, Yanmin ; Liu, Yanke ; Du, Guifen ; Zhang, Wenhao ; Zhou, Lijie ; Zhan, Lihui ; Ren, Xuerui ; Duan, Wenzeng ; Gong, Shuwen</creator><creatorcontrib>Yang, Zeren ; Huo, Yanmin ; Liu, Yanke ; Du, Guifen ; Zhang, Wenhao ; Zhou, Lijie ; Zhan, Lihui ; Ren, Xuerui ; Duan, Wenzeng ; Gong, Shuwen</creatorcontrib><description>By combining the fluorophores of axially chiral 1,1′-binaphthol (BINOL) and 1,4-dihydropyridine derivatives, axially chiral 1,4-dihydropyridine derivatives ((
R
)-/(
S
)-
2
) with aggregation-induced emission (AIE) in exciplexes were designed and synthesized. (
R
)-/(
S
)-
2
emitted low fluorescence in THF solutions of their locally excited states; however, they emitted red-shifted fluorescence in the aggregate state upon exciplex formation. Moreover, (
R
)-/(
S
)-
2
showed linear and multi-exponential relationships between their local excited and exciplex fluorescence intensities and the viscosity of the medium, which allowed us to determine the viscosities of different mixed solvents. In addition, as an axially chiral viscosity probe, (
R
)-/(
S
)-
2
show excellent CD signals and have potential applications in the fields of chiral recognition and fluorescence imaging, which will broaden the new family of AIE fluorophores. To the best of our knowledge, there are few reports of axially chiral intramolecular exciplex-mediated AIE molecules.
Axially chiral 1,4-dihydropyridine derivatives ((
R
)-/(
S
)-
2
) with aggregation-induced emission (AIE) in exciplex were designed and synthesized. They have excellent CD signals and can determine the different viscosity in mixed solvents.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/c9ra06553a</identifier><identifier>PMID: 35530811</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Agglomeration ; Chemical compounds ; Chemistry ; Derivatives ; Emission ; Fluorescence ; Viscosity</subject><ispartof>RSC advances, 2019-10, Vol.9 (55), p.32219-32225</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2019</rights><rights>This journal is © The Royal Society of Chemistry 2019 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c494t-6e10a372b48ec50ef4e77337099867d8791d36b4896e907dcf2f464714afa5663</citedby><cites>FETCH-LOGICAL-c494t-6e10a372b48ec50ef4e77337099867d8791d36b4896e907dcf2f464714afa5663</cites><orcidid>0000-0003-3484-5231 ; 0000-0002-6678-7534</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9072944/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9072944/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,315,729,782,786,866,887,27933,27934,53800,53802</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35530811$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yang, Zeren</creatorcontrib><creatorcontrib>Huo, Yanmin</creatorcontrib><creatorcontrib>Liu, Yanke</creatorcontrib><creatorcontrib>Du, Guifen</creatorcontrib><creatorcontrib>Zhang, Wenhao</creatorcontrib><creatorcontrib>Zhou, Lijie</creatorcontrib><creatorcontrib>Zhan, Lihui</creatorcontrib><creatorcontrib>Ren, Xuerui</creatorcontrib><creatorcontrib>Duan, Wenzeng</creatorcontrib><creatorcontrib>Gong, Shuwen</creatorcontrib><title>Axially chiral 1,4-dihydropyridine derivatives: aggregation-induced emission in exciplexes and application as viscosity probes</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>By combining the fluorophores of axially chiral 1,1′-binaphthol (BINOL) and 1,4-dihydropyridine derivatives, axially chiral 1,4-dihydropyridine derivatives ((
R
)-/(
S
)-
2
) with aggregation-induced emission (AIE) in exciplexes were designed and synthesized. (
R
)-/(
S
)-
2
emitted low fluorescence in THF solutions of their locally excited states; however, they emitted red-shifted fluorescence in the aggregate state upon exciplex formation. Moreover, (
R
)-/(
S
)-
2
showed linear and multi-exponential relationships between their local excited and exciplex fluorescence intensities and the viscosity of the medium, which allowed us to determine the viscosities of different mixed solvents. In addition, as an axially chiral viscosity probe, (
R
)-/(
S
)-
2
show excellent CD signals and have potential applications in the fields of chiral recognition and fluorescence imaging, which will broaden the new family of AIE fluorophores. To the best of our knowledge, there are few reports of axially chiral intramolecular exciplex-mediated AIE molecules.
Axially chiral 1,4-dihydropyridine derivatives ((
R
)-/(
S
)-
2
) with aggregation-induced emission (AIE) in exciplex were designed and synthesized. They have excellent CD signals and can determine the different viscosity in mixed solvents.</description><subject>Agglomeration</subject><subject>Chemical compounds</subject><subject>Chemistry</subject><subject>Derivatives</subject><subject>Emission</subject><subject>Fluorescence</subject><subject>Viscosity</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpdkttrFDEYxQex2FL74rsS8EXE0dwmmfRBWBYvhYIg-hyyyTe7KbPJmMwsOy_-7abdutbmJZfz4_AdTqrqBcHvCWbqg1XJYNE0zDypzijmoqZYqKcPzqfVRc43uCzRECrIs-qUFR63hJxVvxd7b_p-Rnbjk-kRecdr5zezS3GYk3c-AHKQ_M6Mfgf5Epn1OsG63GKofXCTBYdg63MuD8gHBHvrhx72kJEJDplh6L29w5HJaOezjdmPMxpSXEF-Xp10ps9wcb-fVz8_f_qx_Fpff_tytVxc15YrPtYCCDZM0hVvwTYYOg5SMiaxUq2QrpWKOCaKqgQoLJ3taMcFl4SbzjRCsPPq48F3mFZbcBbCWNLqIfmtSbOOxuv_leA3eh13urhRxXkxeHNvkOKvCfKoS2YLfW8CxClrKgThLRWtLOjrR-hNnFIo8TRlmFFCG8wK9fZA2RRzTtAdhyFY3zarl-r74q7ZRYFfPRz_iP7tsQAvD0DK9qj--xrsD_GUqiM</recordid><startdate>20191010</startdate><enddate>20191010</enddate><creator>Yang, Zeren</creator><creator>Huo, Yanmin</creator><creator>Liu, Yanke</creator><creator>Du, Guifen</creator><creator>Zhang, Wenhao</creator><creator>Zhou, Lijie</creator><creator>Zhan, Lihui</creator><creator>Ren, Xuerui</creator><creator>Duan, Wenzeng</creator><creator>Gong, Shuwen</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-3484-5231</orcidid><orcidid>https://orcid.org/0000-0002-6678-7534</orcidid></search><sort><creationdate>20191010</creationdate><title>Axially chiral 1,4-dihydropyridine derivatives: aggregation-induced emission in exciplexes and application as viscosity probes</title><author>Yang, Zeren ; Huo, Yanmin ; Liu, Yanke ; Du, Guifen ; Zhang, Wenhao ; Zhou, Lijie ; Zhan, Lihui ; Ren, Xuerui ; Duan, Wenzeng ; Gong, Shuwen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c494t-6e10a372b48ec50ef4e77337099867d8791d36b4896e907dcf2f464714afa5663</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Agglomeration</topic><topic>Chemical compounds</topic><topic>Chemistry</topic><topic>Derivatives</topic><topic>Emission</topic><topic>Fluorescence</topic><topic>Viscosity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Zeren</creatorcontrib><creatorcontrib>Huo, Yanmin</creatorcontrib><creatorcontrib>Liu, Yanke</creatorcontrib><creatorcontrib>Du, Guifen</creatorcontrib><creatorcontrib>Zhang, Wenhao</creatorcontrib><creatorcontrib>Zhou, Lijie</creatorcontrib><creatorcontrib>Zhan, Lihui</creatorcontrib><creatorcontrib>Ren, Xuerui</creatorcontrib><creatorcontrib>Duan, Wenzeng</creatorcontrib><creatorcontrib>Gong, Shuwen</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yang, Zeren</au><au>Huo, Yanmin</au><au>Liu, Yanke</au><au>Du, Guifen</au><au>Zhang, Wenhao</au><au>Zhou, Lijie</au><au>Zhan, Lihui</au><au>Ren, Xuerui</au><au>Duan, Wenzeng</au><au>Gong, Shuwen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Axially chiral 1,4-dihydropyridine derivatives: aggregation-induced emission in exciplexes and application as viscosity probes</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2019-10-10</date><risdate>2019</risdate><volume>9</volume><issue>55</issue><spage>32219</spage><epage>32225</epage><pages>32219-32225</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>By combining the fluorophores of axially chiral 1,1′-binaphthol (BINOL) and 1,4-dihydropyridine derivatives, axially chiral 1,4-dihydropyridine derivatives ((
R
)-/(
S
)-
2
) with aggregation-induced emission (AIE) in exciplexes were designed and synthesized. (
R
)-/(
S
)-
2
emitted low fluorescence in THF solutions of their locally excited states; however, they emitted red-shifted fluorescence in the aggregate state upon exciplex formation. Moreover, (
R
)-/(
S
)-
2
showed linear and multi-exponential relationships between their local excited and exciplex fluorescence intensities and the viscosity of the medium, which allowed us to determine the viscosities of different mixed solvents. In addition, as an axially chiral viscosity probe, (
R
)-/(
S
)-
2
show excellent CD signals and have potential applications in the fields of chiral recognition and fluorescence imaging, which will broaden the new family of AIE fluorophores. To the best of our knowledge, there are few reports of axially chiral intramolecular exciplex-mediated AIE molecules.
Axially chiral 1,4-dihydropyridine derivatives ((
R
)-/(
S
)-
2
) with aggregation-induced emission (AIE) in exciplex were designed and synthesized. They have excellent CD signals and can determine the different viscosity in mixed solvents.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>35530811</pmid><doi>10.1039/c9ra06553a</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0003-3484-5231</orcidid><orcidid>https://orcid.org/0000-0002-6678-7534</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | RSC advances, 2019-10, Vol.9 (55), p.32219-32225 |
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| language | eng |
| recordid | cdi_rsc_primary_c9ra06553a |
| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central Open Access; PubMed Central |
| subjects | Agglomeration Chemical compounds Chemistry Derivatives Emission Fluorescence Viscosity |
| title | Axially chiral 1,4-dihydropyridine derivatives: aggregation-induced emission in exciplexes and application as viscosity probes |
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