Two novel aggregation-induced emission active coumarin-based Schiff bases and their applications in cell imaging
Two new coumarin-based Schiff bases, 8,8′-((1 E ,1′ E )-hydrazine-1,2-diylidenebis(methanylylidene))bis(7-hydroxy-4-methyl-2 H -chromen-2-one), (CHC), and 7-hydroxy-8-(( E )-(( E )-((2-hydroxynaphthalen-1-yl)methylene)hydrazono)methyl)-4-methyl-2 H -chromen-2-one, (CHN), with excited-state intramole...
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| Veröffentlicht in: | New journal of chemistry 2014, Vol.38 (6), p.2386-2393 |
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| container_title | New journal of chemistry |
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| creator | Xiao, Hongde Chen, Kun Cui, Dandan Jiang, Nannan Yin, Gui Wang, Jie Wang, Ruiyong |
| description | Two new coumarin-based Schiff bases, 8,8′-((1
E
,1′
E
)-hydrazine-1,2-diylidenebis(methanylylidene))bis(7-hydroxy-4-methyl-2
H
-chromen-2-one), (CHC), and 7-hydroxy-8-((
E
)-((
E
)-((2-hydroxynaphthalen-1-yl)methylene)hydrazono)methyl)-4-methyl-2
H
-chromen-2-one, (CHN), with excited-state intramolecular proton-transfer (ESIPT) properties, were synthesized and characterized. Both of the compounds displayed aggregation-induced emission (AIE) characteristics, of which CHC nanoparticles emitted a reddish orange fluorescence, while the CHN nanoparticles exhibited a saffron yellow fluorescence. The appearance of emission peaks in the long wave regions with large Stokes-shifts demonstrated the occurrence of the ESIPT process. Observations of the nanoparticles' morphologies were undertaken through a transmission electron microscope (TEM) method. Furthermore, due to the good biocompatibilities, high stabilities and the large Stokes-shifts, the two compounds were ideal candidates for cell staining. |
| doi_str_mv | 10.1039/C3NJ01557B |
| format | Article |
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E
,1′
E
)-hydrazine-1,2-diylidenebis(methanylylidene))bis(7-hydroxy-4-methyl-2
H
-chromen-2-one), (CHC), and 7-hydroxy-8-((
E
)-((
E
)-((2-hydroxynaphthalen-1-yl)methylene)hydrazono)methyl)-4-methyl-2
H
-chromen-2-one, (CHN), with excited-state intramolecular proton-transfer (ESIPT) properties, were synthesized and characterized. Both of the compounds displayed aggregation-induced emission (AIE) characteristics, of which CHC nanoparticles emitted a reddish orange fluorescence, while the CHN nanoparticles exhibited a saffron yellow fluorescence. The appearance of emission peaks in the long wave regions with large Stokes-shifts demonstrated the occurrence of the ESIPT process. Observations of the nanoparticles' morphologies were undertaken through a transmission electron microscope (TEM) method. Furthermore, due to the good biocompatibilities, high stabilities and the large Stokes-shifts, the two compounds were ideal candidates for cell staining.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/C3NJ01557B</identifier><language>eng</language><ispartof>New journal of chemistry, 2014, Vol.38 (6), p.2386-2393</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c231t-a719b9e3fdabce91170beb5cdef164317fafd3f568dd645c8caf72b210cd03c03</citedby><cites>FETCH-LOGICAL-c231t-a719b9e3fdabce91170beb5cdef164317fafd3f568dd645c8caf72b210cd03c03</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,4010,27900,27901,27902</link.rule.ids></links><search><creatorcontrib>Xiao, Hongde</creatorcontrib><creatorcontrib>Chen, Kun</creatorcontrib><creatorcontrib>Cui, Dandan</creatorcontrib><creatorcontrib>Jiang, Nannan</creatorcontrib><creatorcontrib>Yin, Gui</creatorcontrib><creatorcontrib>Wang, Jie</creatorcontrib><creatorcontrib>Wang, Ruiyong</creatorcontrib><title>Two novel aggregation-induced emission active coumarin-based Schiff bases and their applications in cell imaging</title><title>New journal of chemistry</title><description>Two new coumarin-based Schiff bases, 8,8′-((1
E
,1′
E
)-hydrazine-1,2-diylidenebis(methanylylidene))bis(7-hydroxy-4-methyl-2
H
-chromen-2-one), (CHC), and 7-hydroxy-8-((
E
)-((
E
)-((2-hydroxynaphthalen-1-yl)methylene)hydrazono)methyl)-4-methyl-2
H
-chromen-2-one, (CHN), with excited-state intramolecular proton-transfer (ESIPT) properties, were synthesized and characterized. Both of the compounds displayed aggregation-induced emission (AIE) characteristics, of which CHC nanoparticles emitted a reddish orange fluorescence, while the CHN nanoparticles exhibited a saffron yellow fluorescence. The appearance of emission peaks in the long wave regions with large Stokes-shifts demonstrated the occurrence of the ESIPT process. Observations of the nanoparticles' morphologies were undertaken through a transmission electron microscope (TEM) method. Furthermore, due to the good biocompatibilities, high stabilities and the large Stokes-shifts, the two compounds were ideal candidates for cell staining.</description><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNpFUMtKxDAUDaLg-Nj4BVkL0dymTadLHXwy6MJxXW5vkk6kk5akM-Lf21HB1XnB4XAYuwB5BVJV1wv18iyhKMrbAzYDpStRZRoOJw55LmSR62N2ktKHlAClhhkbVp89D_3OdhzbNtoWR98H4YPZkjXcbnxKk8GRRr-znPrtBqMPosE0xW-09s7xvUgcg-Hj2vrIcRg6Tz9NifvAyXYd9xtsfWjP2JHDLtnzPzxl7_d3q8WjWL4-PC1uloIyBaPAEqqmssoZbMhW01rZ2KYgYx3oXEHp0BnlCj03RucFzQldmTUZSDJSkVSn7PK3l2KfUrSuHuI0IX7VIOv9V_X_V-obOalfMg</recordid><startdate>2014</startdate><enddate>2014</enddate><creator>Xiao, Hongde</creator><creator>Chen, Kun</creator><creator>Cui, Dandan</creator><creator>Jiang, Nannan</creator><creator>Yin, Gui</creator><creator>Wang, Jie</creator><creator>Wang, Ruiyong</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>2014</creationdate><title>Two novel aggregation-induced emission active coumarin-based Schiff bases and their applications in cell imaging</title><author>Xiao, Hongde ; Chen, Kun ; Cui, Dandan ; Jiang, Nannan ; Yin, Gui ; Wang, Jie ; Wang, Ruiyong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c231t-a719b9e3fdabce91170beb5cdef164317fafd3f568dd645c8caf72b210cd03c03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xiao, Hongde</creatorcontrib><creatorcontrib>Chen, Kun</creatorcontrib><creatorcontrib>Cui, Dandan</creatorcontrib><creatorcontrib>Jiang, Nannan</creatorcontrib><creatorcontrib>Yin, Gui</creatorcontrib><creatorcontrib>Wang, Jie</creatorcontrib><creatorcontrib>Wang, Ruiyong</creatorcontrib><collection>CrossRef</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xiao, Hongde</au><au>Chen, Kun</au><au>Cui, Dandan</au><au>Jiang, Nannan</au><au>Yin, Gui</au><au>Wang, Jie</au><au>Wang, Ruiyong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Two novel aggregation-induced emission active coumarin-based Schiff bases and their applications in cell imaging</atitle><jtitle>New journal of chemistry</jtitle><date>2014</date><risdate>2014</risdate><volume>38</volume><issue>6</issue><spage>2386</spage><epage>2393</epage><pages>2386-2393</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>Two new coumarin-based Schiff bases, 8,8′-((1
E
,1′
E
)-hydrazine-1,2-diylidenebis(methanylylidene))bis(7-hydroxy-4-methyl-2
H
-chromen-2-one), (CHC), and 7-hydroxy-8-((
E
)-((
E
)-((2-hydroxynaphthalen-1-yl)methylene)hydrazono)methyl)-4-methyl-2
H
-chromen-2-one, (CHN), with excited-state intramolecular proton-transfer (ESIPT) properties, were synthesized and characterized. Both of the compounds displayed aggregation-induced emission (AIE) characteristics, of which CHC nanoparticles emitted a reddish orange fluorescence, while the CHN nanoparticles exhibited a saffron yellow fluorescence. The appearance of emission peaks in the long wave regions with large Stokes-shifts demonstrated the occurrence of the ESIPT process. Observations of the nanoparticles' morphologies were undertaken through a transmission electron microscope (TEM) method. Furthermore, due to the good biocompatibilities, high stabilities and the large Stokes-shifts, the two compounds were ideal candidates for cell staining.</abstract><doi>10.1039/C3NJ01557B</doi><tpages>8</tpages></addata></record> |
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| ispartof | New journal of chemistry, 2014, Vol.38 (6), p.2386-2393 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| title | Two novel aggregation-induced emission active coumarin-based Schiff bases and their applications in cell imaging |
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