Aggregation-induced emission enhancement (AIEE)-active boron-difluoride dyes with reversible mechanochromic fluorescence
A novel class of solid-emissive boron-difluoride derivatives, using phenanthrenequinone hydrazone as ligands, were designed and efficiently synthesized. These dyes exhibit weak fluorescence in dilute solutions, but much higher fluorescence efficiency in aggregate states with a large stokes shift (ov...
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| Veröffentlicht in: | RSC advances 2019-11, Vol.9 (61), p.35872-35877 |
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| container_issue | 61 |
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| creator | Yan, Xiaojing Zhu, Pengcheng Zhou, Zhiguo Yang, Hong Lan, Haichuang Xiao, Shuzhang |
| description | A novel class of solid-emissive boron-difluoride derivatives, using phenanthrenequinone hydrazone as ligands, were designed and efficiently synthesized. These dyes exhibit weak fluorescence in dilute solutions, but much higher fluorescence efficiency in aggregate states with a large stokes shift (over 70 nm) due to the their aggregation-induced emission enhancement (AIEE) characteristics. According to their photophysical properties and X-ray single crystal structure analysis, the AIEE was ascribed to the H(J)-aggregate formation aided by multiple intermolecular interactions to restrict intramolecular motion in the solid state. Moreover, their solid emissions could be reversibly tuned between "on" and "off" by mechanical grinding and recrystallization, due to the stacking model transition between H(J)-aggregation with loose molecular packing and J-aggregation with intense intermolecular interactions.
A class of AIEE-active mechanochromic boron-difluorides were reported, and the mechanochromism was ascribed to the transition between H(J)-aggregation with loose molecular packing and J-aggregation with intense intermolecular interactions. |
| doi_str_mv | 10.1039/c9ra07437f |
| format | Article |
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A class of AIEE-active mechanochromic boron-difluorides were reported, and the mechanochromism was ascribed to the transition between H(J)-aggregation with loose molecular packing and J-aggregation with intense intermolecular interactions.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/c9ra07437f</identifier><identifier>PMID: 35528054</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Agglomeration ; Boron ; Chemistry ; Crystal structure ; Crystallography ; Difluorides ; Dyes ; Emission ; Fluorescence ; Hydrazones ; Mechanoluminescence ; Recrystallization ; Single crystals ; Structural analysis</subject><ispartof>RSC advances, 2019-11, Vol.9 (61), p.35872-35877</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-c428t-cbd46e2918169ca8e0a5a4d2213989a3f43bd0c4f40de28f9aa4d14b44b402343</citedby><cites>FETCH-LOGICAL-c428t-cbd46e2918169ca8e0a5a4d2213989a3f43bd0c4f40de28f9aa4d14b44b402343</cites><orcidid>0000-0001-9570-6986 ; 0000-0001-5952-8836</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/PMC9074698/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9074698/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35528054$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yan, Xiaojing</creatorcontrib><creatorcontrib>Zhu, Pengcheng</creatorcontrib><creatorcontrib>Zhou, Zhiguo</creatorcontrib><creatorcontrib>Yang, Hong</creatorcontrib><creatorcontrib>Lan, Haichuang</creatorcontrib><creatorcontrib>Xiao, Shuzhang</creatorcontrib><title>Aggregation-induced emission enhancement (AIEE)-active boron-difluoride dyes with reversible mechanochromic fluorescence</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>A novel class of solid-emissive boron-difluoride derivatives, using phenanthrenequinone hydrazone as ligands, were designed and efficiently synthesized. These dyes exhibit weak fluorescence in dilute solutions, but much higher fluorescence efficiency in aggregate states with a large stokes shift (over 70 nm) due to the their aggregation-induced emission enhancement (AIEE) characteristics. According to their photophysical properties and X-ray single crystal structure analysis, the AIEE was ascribed to the H(J)-aggregate formation aided by multiple intermolecular interactions to restrict intramolecular motion in the solid state. Moreover, their solid emissions could be reversibly tuned between "on" and "off" by mechanical grinding and recrystallization, due to the stacking model transition between H(J)-aggregation with loose molecular packing and J-aggregation with intense intermolecular interactions.
A class of AIEE-active mechanochromic boron-difluorides were reported, and the mechanochromism was ascribed to the transition between H(J)-aggregation with loose molecular packing and J-aggregation with intense intermolecular interactions.</description><subject>Agglomeration</subject><subject>Boron</subject><subject>Chemistry</subject><subject>Crystal structure</subject><subject>Crystallography</subject><subject>Difluorides</subject><subject>Dyes</subject><subject>Emission</subject><subject>Fluorescence</subject><subject>Hydrazones</subject><subject>Mechanoluminescence</subject><subject>Recrystallization</subject><subject>Single crystals</subject><subject>Structural analysis</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpdkl1LHDEUhkNRqlhveq8EvLGFsfmamNwIy7K2giCIvQ6Z5MxuZGaiycy2_vumrt2qIZCQ9zlvTs4JQp8pOaOE629OJ0vOBT9vP6B9RoSsGJF659V-Dx3mfE_KkDVlkn5Ee7yumSK12Ee_Z8tlgqUdQxyqMPjJgcfQh5zLAYZhZQcHPQwjPp1dLRZfKuvGsAbcxFQCfGi7KabgAfsnyPhXGFc4wRpSDk0HuAdXDKJbpdgHh59hyA6K5ye029ouw-HLeoB-Xi7u5j-q65vvV_PZdeUEU2PlGi8kME0VldpZBcTWVnjGKNdKW94K3njiRCuIB6ZabYtKRSPKJIwLfoAuNr4PU9ODL3ePyXbmIYXepicTbTBvlSGszDKujS5VlVoVg9MXgxQfJ8ijKdVx0HV2gDhlw6SkQgld64KevEPv45SG8jzDOGVCK6lYob5uKJdizgnabTKUmL89NXN9O3vu6WWBj1-nv0X_dbAARxsgZbdV_38K_gf8Rqib</recordid><startdate>20191104</startdate><enddate>20191104</enddate><creator>Yan, Xiaojing</creator><creator>Zhu, Pengcheng</creator><creator>Zhou, Zhiguo</creator><creator>Yang, Hong</creator><creator>Lan, Haichuang</creator><creator>Xiao, Shuzhang</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/0000-0001-9570-6986</orcidid><orcidid>https://orcid.org/0000-0001-5952-8836</orcidid></search><sort><creationdate>20191104</creationdate><title>Aggregation-induced emission enhancement (AIEE)-active boron-difluoride dyes with reversible mechanochromic fluorescence</title><author>Yan, Xiaojing ; Zhu, Pengcheng ; Zhou, Zhiguo ; Yang, Hong ; Lan, Haichuang ; Xiao, Shuzhang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c428t-cbd46e2918169ca8e0a5a4d2213989a3f43bd0c4f40de28f9aa4d14b44b402343</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Agglomeration</topic><topic>Boron</topic><topic>Chemistry</topic><topic>Crystal structure</topic><topic>Crystallography</topic><topic>Difluorides</topic><topic>Dyes</topic><topic>Emission</topic><topic>Fluorescence</topic><topic>Hydrazones</topic><topic>Mechanoluminescence</topic><topic>Recrystallization</topic><topic>Single crystals</topic><topic>Structural analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yan, Xiaojing</creatorcontrib><creatorcontrib>Zhu, Pengcheng</creatorcontrib><creatorcontrib>Zhou, Zhiguo</creatorcontrib><creatorcontrib>Yang, Hong</creatorcontrib><creatorcontrib>Lan, Haichuang</creatorcontrib><creatorcontrib>Xiao, Shuzhang</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>Yan, Xiaojing</au><au>Zhu, Pengcheng</au><au>Zhou, Zhiguo</au><au>Yang, Hong</au><au>Lan, Haichuang</au><au>Xiao, Shuzhang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Aggregation-induced emission enhancement (AIEE)-active boron-difluoride dyes with reversible mechanochromic fluorescence</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2019-11-04</date><risdate>2019</risdate><volume>9</volume><issue>61</issue><spage>35872</spage><epage>35877</epage><pages>35872-35877</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>A novel class of solid-emissive boron-difluoride derivatives, using phenanthrenequinone hydrazone as ligands, were designed and efficiently synthesized. These dyes exhibit weak fluorescence in dilute solutions, but much higher fluorescence efficiency in aggregate states with a large stokes shift (over 70 nm) due to the their aggregation-induced emission enhancement (AIEE) characteristics. According to their photophysical properties and X-ray single crystal structure analysis, the AIEE was ascribed to the H(J)-aggregate formation aided by multiple intermolecular interactions to restrict intramolecular motion in the solid state. Moreover, their solid emissions could be reversibly tuned between "on" and "off" by mechanical grinding and recrystallization, due to the stacking model transition between H(J)-aggregation with loose molecular packing and J-aggregation with intense intermolecular interactions.
A class of AIEE-active mechanochromic boron-difluorides were reported, and the mechanochromism was ascribed to the transition between H(J)-aggregation with loose molecular packing and J-aggregation with intense intermolecular interactions.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>35528054</pmid><doi>10.1039/c9ra07437f</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-9570-6986</orcidid><orcidid>https://orcid.org/0000-0001-5952-8836</orcidid><oa>free_for_read</oa></addata></record> |
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central; PubMed Central Open Access |
| subjects | Agglomeration Boron Chemistry Crystal structure Crystallography Difluorides Dyes Emission Fluorescence Hydrazones Mechanoluminescence Recrystallization Single crystals Structural analysis |
| title | Aggregation-induced emission enhancement (AIEE)-active boron-difluoride dyes with reversible mechanochromic fluorescence |
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