J-Aggregation induced emission enhancement of a thienyl substituted bis(difluoroboron)-1,2-bis((1 H -pyrrol-2-yl)methylene)hydrazine (BOPHY) dye
The synthesis and characterization of 2,7-diphenyl- and 2,7-dithienyl-1,3,6,8-tetramethyl bis(difluoroboron)-1,2-bis((1 H -pyrrol-2-yl)methylene)hydrazine (BOPHY) derivatives 1 and 2 are described. The compounds were characterized by NMR ( 1 H, 13 C), X-ray single crystal diffraction analysis, UV/Vi...
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| Veröffentlicht in: | New journal of chemistry 2018, Vol.42 (10), p.8271-8275 |
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| creator | Jiang, Liang Gao, Hu Gai, Lizhi Shen, Zhen |
| description | The synthesis and characterization of 2,7-diphenyl- and 2,7-dithienyl-1,3,6,8-tetramethyl bis(difluoroboron)-1,2-bis((1
H
-pyrrol-2-yl)methylene)hydrazine (BOPHY) derivatives
1
and
2
are described. The compounds were characterized by NMR (
1
H,
13
C), X-ray single crystal diffraction analysis, UV/Vis, fluorescence spectroscopy and high-resolution mass spectrometry (HRMS). The photophysical properties were investigated in solvents of different polarities. Compound
1
exhibits slight solvent dependent spectroscopic properties, whereas compound
2
shows fluorescence quenching with an increase in the solvent polarity. Aggregation-induced emission enhancement (AIEE) is observed in compound
2
, which is attributed to the formation of J-aggregates that result in narrow, red-shifted and enhanced emission. Modification of the β-substituents of BOPHY is responsible for the formation of these aggregates, which is definitively established by an X-ray diffraction study. |
| doi_str_mv | 10.1039/C8NJ00031J |
| format | Article |
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H
-pyrrol-2-yl)methylene)hydrazine (BOPHY) derivatives
1
and
2
are described. The compounds were characterized by NMR (
1
H,
13
C), X-ray single crystal diffraction analysis, UV/Vis, fluorescence spectroscopy and high-resolution mass spectrometry (HRMS). The photophysical properties were investigated in solvents of different polarities. Compound
1
exhibits slight solvent dependent spectroscopic properties, whereas compound
2
shows fluorescence quenching with an increase in the solvent polarity. Aggregation-induced emission enhancement (AIEE) is observed in compound
2
, which is attributed to the formation of J-aggregates that result in narrow, red-shifted and enhanced emission. Modification of the β-substituents of BOPHY is responsible for the formation of these aggregates, which is definitively established by an X-ray diffraction study.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/C8NJ00031J</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Agglomeration ; Aggregates ; Fluorescence ; Hydrazines ; Mass spectrometry ; Methylene ; NMR ; Nuclear magnetic resonance ; Polarity ; Single crystals ; X-ray diffraction</subject><ispartof>New journal of chemistry, 2018, Vol.42 (10), p.8271-8275</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c325t-5ff25ca70f3edfbacc3c5fb12940a328718ee119862279b2124dfdbc29675c33</citedby><cites>FETCH-LOGICAL-c325t-5ff25ca70f3edfbacc3c5fb12940a328718ee119862279b2124dfdbc29675c33</cites><orcidid>0000-0003-2464-1278 ; 0000-0001-6361-1448</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,4021,27921,27922,27923</link.rule.ids></links><search><creatorcontrib>Jiang, Liang</creatorcontrib><creatorcontrib>Gao, Hu</creatorcontrib><creatorcontrib>Gai, Lizhi</creatorcontrib><creatorcontrib>Shen, Zhen</creatorcontrib><title>J-Aggregation induced emission enhancement of a thienyl substituted bis(difluoroboron)-1,2-bis((1 H -pyrrol-2-yl)methylene)hydrazine (BOPHY) dye</title><title>New journal of chemistry</title><description>The synthesis and characterization of 2,7-diphenyl- and 2,7-dithienyl-1,3,6,8-tetramethyl bis(difluoroboron)-1,2-bis((1
H
-pyrrol-2-yl)methylene)hydrazine (BOPHY) derivatives
1
and
2
are described. The compounds were characterized by NMR (
1
H,
13
C), X-ray single crystal diffraction analysis, UV/Vis, fluorescence spectroscopy and high-resolution mass spectrometry (HRMS). The photophysical properties were investigated in solvents of different polarities. Compound
1
exhibits slight solvent dependent spectroscopic properties, whereas compound
2
shows fluorescence quenching with an increase in the solvent polarity. Aggregation-induced emission enhancement (AIEE) is observed in compound
2
, which is attributed to the formation of J-aggregates that result in narrow, red-shifted and enhanced emission. Modification of the β-substituents of BOPHY is responsible for the formation of these aggregates, which is definitively established by an X-ray diffraction study.</description><subject>Agglomeration</subject><subject>Aggregates</subject><subject>Fluorescence</subject><subject>Hydrazines</subject><subject>Mass spectrometry</subject><subject>Methylene</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Polarity</subject><subject>Single crystals</subject><subject>X-ray diffraction</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpFkM1KAzEUhQdRUKsbnyDgphWjucn8LrWotRTrwo2rIZO56USmmZpkFuNT-MhOUXBxOZfDxzlwougC2A0wUdzO85clY0zA8iA6AZEWtOApHI4_xDFlSZweR6fefzAGkKVwEn0v6d1m43Ajg-ksMbbuFdYEt8b7vYG2kVbhFm0gnSaShMagHVri-8oHE_ow0pXx09rotu9cV41nZxSuOd3bUyALQneDc11LOR3a2RZDM7RocdYMtZNfxiKZ3q9fF-8zUg94Fh1p2Xo8_9NJ9Pb48DZf0NX66Xl-t6JK8CTQRGueKJkxLbDWlVRKqERXwIuYScHzDHJEgCJPOc-KigOPa11XihdplighJtHlb-zOdZ89-lB-dL2zY2PJmchFypK8GKmrX0q5znuHutw5s5VuKIGV-8HL_8HFD2_zcxs</recordid><startdate>2018</startdate><enddate>2018</enddate><creator>Jiang, Liang</creator><creator>Gao, Hu</creator><creator>Gai, Lizhi</creator><creator>Shen, Zhen</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0003-2464-1278</orcidid><orcidid>https://orcid.org/0000-0001-6361-1448</orcidid></search><sort><creationdate>2018</creationdate><title>J-Aggregation induced emission enhancement of a thienyl substituted bis(difluoroboron)-1,2-bis((1 H -pyrrol-2-yl)methylene)hydrazine (BOPHY) dye</title><author>Jiang, Liang ; Gao, Hu ; Gai, Lizhi ; Shen, Zhen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c325t-5ff25ca70f3edfbacc3c5fb12940a328718ee119862279b2124dfdbc29675c33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Agglomeration</topic><topic>Aggregates</topic><topic>Fluorescence</topic><topic>Hydrazines</topic><topic>Mass spectrometry</topic><topic>Methylene</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Polarity</topic><topic>Single crystals</topic><topic>X-ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jiang, Liang</creatorcontrib><creatorcontrib>Gao, Hu</creatorcontrib><creatorcontrib>Gai, Lizhi</creatorcontrib><creatorcontrib>Shen, Zhen</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jiang, Liang</au><au>Gao, Hu</au><au>Gai, Lizhi</au><au>Shen, Zhen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>J-Aggregation induced emission enhancement of a thienyl substituted bis(difluoroboron)-1,2-bis((1 H -pyrrol-2-yl)methylene)hydrazine (BOPHY) dye</atitle><jtitle>New journal of chemistry</jtitle><date>2018</date><risdate>2018</risdate><volume>42</volume><issue>10</issue><spage>8271</spage><epage>8275</epage><pages>8271-8275</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>The synthesis and characterization of 2,7-diphenyl- and 2,7-dithienyl-1,3,6,8-tetramethyl bis(difluoroboron)-1,2-bis((1
H
-pyrrol-2-yl)methylene)hydrazine (BOPHY) derivatives
1
and
2
are described. The compounds were characterized by NMR (
1
H,
13
C), X-ray single crystal diffraction analysis, UV/Vis, fluorescence spectroscopy and high-resolution mass spectrometry (HRMS). The photophysical properties were investigated in solvents of different polarities. Compound
1
exhibits slight solvent dependent spectroscopic properties, whereas compound
2
shows fluorescence quenching with an increase in the solvent polarity. Aggregation-induced emission enhancement (AIEE) is observed in compound
2
, which is attributed to the formation of J-aggregates that result in narrow, red-shifted and enhanced emission. Modification of the β-substituents of BOPHY is responsible for the formation of these aggregates, which is definitively established by an X-ray diffraction study.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/C8NJ00031J</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-2464-1278</orcidid><orcidid>https://orcid.org/0000-0001-6361-1448</orcidid></addata></record> |
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| ispartof | New journal of chemistry, 2018, Vol.42 (10), p.8271-8275 |
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| language | eng |
| recordid | cdi_proquest_journals_2038360589 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Agglomeration Aggregates Fluorescence Hydrazines Mass spectrometry Methylene NMR Nuclear magnetic resonance Polarity Single crystals X-ray diffraction |
| title | J-Aggregation induced emission enhancement of a thienyl substituted bis(difluoroboron)-1,2-bis((1 H -pyrrol-2-yl)methylene)hydrazine (BOPHY) dye |
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