Circularly polarized luminescence (CPL) characteristics of hydrophobic pyrene derivatives/γ-cyclodextrin (γ-CD) complexes in aqueous solution dissolved by grinding
Circularly polarized luminescence (CPL) organic dyes are currently receiving a great interest, but there are still not many reported observations of CPL spectra of hydrophobic dyes from aqueous solution. We have prepared hydrophobic pyrene derivatives and dissolved them into aqueous solutions with γ...
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| Veröffentlicht in: | Journal of inclusion phenomena and macrocyclic chemistry 2022-02, Vol.102 (1-2), p.133-142 |
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| container_title | Journal of inclusion phenomena and macrocyclic chemistry |
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| creator | Sawai, Mika Matsumoto, Sayaka Mimura, Yuki Imai, Yoshitane Yamazaki, Shoko Kanehisa, Nobuko Tohnai, Norimitsu Nakata, Eiji Takashima, Hiroshi |
| description | Circularly polarized luminescence (CPL) organic dyes are currently receiving a great interest, but there are still not many reported observations of CPL spectra of hydrophobic dyes from aqueous solution. We have prepared hydrophobic pyrene derivatives and dissolved them into aqueous solutions with
γ
-cyclodextrin (
γ
-CD) by using grinding technique. Among these derivatives, (pyrene-1-carbonyl)serine (PySer) forms a spatially restricted dimer in the hydrophobic chiral cavity of
γ
-CD and exhibits excimer emission with a high quantum yield of
Φ
f
= 0.68. In addition, circular dichroism and CPL signals were induced for the complex. The strong
g
CPL
value of
g
CPL
= + 2.2 × 10
−3
was obtained, which may be attributed to the interaction between the hydroxyl groups in the side chain of PySer with those of
γ
-CD and it strengthens the chiral dimeric structure.
Graphic abstract |
| doi_str_mv | 10.1007/s10847-021-01108-z |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2619557929</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2619557929</sourcerecordid><originalsourceid>FETCH-LOGICAL-c249t-8d5fd33a665853f493ba3754ce6fe10401a05f01cb494b23267f264f78540ffa3</originalsourceid><addsrcrecordid>eNp9Uctu1EAQtBBIJIEf4DRSLslhyDz9OCInPKSV4ADn0XjcszuR12Nm7FW8_5Mv4D_4JposUm70pUvdVdUtVVG84-w9Z6y6yZzVqqJMcMo4Ynp8UZxxXUnKsV4ilnVNJRfV6-I853vGRCmUPCse25DcMtg0rGSK2MMRejIs-zBCdjA6IFftt801cTubrJshhTwHl0n0ZLf2KU672AVHpjXBCKTH_cHO4QD55vcv6lY3xB4e5hRGcoWD9had4n4a4AEywaH9uUBcMslxWOYQR9KHjPiAT3Qr2aKuD-P2TfHK2yHD23_9ovjx8e57-5luvn760n7YUCdUM9O6176X0palrrX0qpGdlZVWDkoPnCnGLdOecdepRnVCirLyolS-qrVi3lt5UVyefKcU8bE8m_u4pBFPGlHyRuuqEQ2yxInlUsw5gTdTCnubVsOZ-RuHOcVhMA7zFIc5okieRBnJ4xbSs_V_VH8AIqOTAA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2619557929</pqid></control><display><type>article</type><title>Circularly polarized luminescence (CPL) characteristics of hydrophobic pyrene derivatives/γ-cyclodextrin (γ-CD) complexes in aqueous solution dissolved by grinding</title><source>Springer Nature - Complete Springer Journals</source><creator>Sawai, Mika ; Matsumoto, Sayaka ; Mimura, Yuki ; Imai, Yoshitane ; Yamazaki, Shoko ; Kanehisa, Nobuko ; Tohnai, Norimitsu ; Nakata, Eiji ; Takashima, Hiroshi</creator><creatorcontrib>Sawai, Mika ; Matsumoto, Sayaka ; Mimura, Yuki ; Imai, Yoshitane ; Yamazaki, Shoko ; Kanehisa, Nobuko ; Tohnai, Norimitsu ; Nakata, Eiji ; Takashima, Hiroshi</creatorcontrib><description>Circularly polarized luminescence (CPL) organic dyes are currently receiving a great interest, but there are still not many reported observations of CPL spectra of hydrophobic dyes from aqueous solution. We have prepared hydrophobic pyrene derivatives and dissolved them into aqueous solutions with
γ
-cyclodextrin (
γ
-CD) by using grinding technique. Among these derivatives, (pyrene-1-carbonyl)serine (PySer) forms a spatially restricted dimer in the hydrophobic chiral cavity of
γ
-CD and exhibits excimer emission with a high quantum yield of
Φ
f
= 0.68. In addition, circular dichroism and CPL signals were induced for the complex. The strong
g
CPL
value of
g
CPL
= + 2.2 × 10
−3
was obtained, which may be attributed to the interaction between the hydroxyl groups in the side chain of PySer with those of
γ
-CD and it strengthens the chiral dimeric structure.
Graphic abstract</description><identifier>ISSN: 1388-3127</identifier><identifier>EISSN: 1573-1111</identifier><identifier>DOI: 10.1007/s10847-021-01108-z</identifier><language>eng</language><publisher>Dordrecht: Springer Netherlands</publisher><subject>Aqueous solutions ; Carbonyls ; Chemistry ; Chemistry and Materials Science ; Circular polarization ; Crystallography and Scattering Methods ; Cyclodextrins ; Dichroism ; Dimers ; Dyes ; Excimers ; Food Science ; Grinding ; Hydrophobicity ; Hydroxyl groups ; Luminescence ; Organic Chemistry ; Original Article</subject><ispartof>Journal of inclusion phenomena and macrocyclic chemistry, 2022-02, Vol.102 (1-2), p.133-142</ispartof><rights>The Author(s), under exclusive licence to Springer Nature B.V. 2021</rights><rights>The Author(s), under exclusive licence to Springer Nature B.V. 2021.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c249t-8d5fd33a665853f493ba3754ce6fe10401a05f01cb494b23267f264f78540ffa3</citedby><cites>FETCH-LOGICAL-c249t-8d5fd33a665853f493ba3754ce6fe10401a05f01cb494b23267f264f78540ffa3</cites><orcidid>0000-0001-6875-8254</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s10847-021-01108-z$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10847-021-01108-z$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27903,27904,41467,42536,51297</link.rule.ids></links><search><creatorcontrib>Sawai, Mika</creatorcontrib><creatorcontrib>Matsumoto, Sayaka</creatorcontrib><creatorcontrib>Mimura, Yuki</creatorcontrib><creatorcontrib>Imai, Yoshitane</creatorcontrib><creatorcontrib>Yamazaki, Shoko</creatorcontrib><creatorcontrib>Kanehisa, Nobuko</creatorcontrib><creatorcontrib>Tohnai, Norimitsu</creatorcontrib><creatorcontrib>Nakata, Eiji</creatorcontrib><creatorcontrib>Takashima, Hiroshi</creatorcontrib><title>Circularly polarized luminescence (CPL) characteristics of hydrophobic pyrene derivatives/γ-cyclodextrin (γ-CD) complexes in aqueous solution dissolved by grinding</title><title>Journal of inclusion phenomena and macrocyclic chemistry</title><addtitle>J Incl Phenom Macrocycl Chem</addtitle><description>Circularly polarized luminescence (CPL) organic dyes are currently receiving a great interest, but there are still not many reported observations of CPL spectra of hydrophobic dyes from aqueous solution. We have prepared hydrophobic pyrene derivatives and dissolved them into aqueous solutions with
γ
-cyclodextrin (
γ
-CD) by using grinding technique. Among these derivatives, (pyrene-1-carbonyl)serine (PySer) forms a spatially restricted dimer in the hydrophobic chiral cavity of
γ
-CD and exhibits excimer emission with a high quantum yield of
Φ
f
= 0.68. In addition, circular dichroism and CPL signals were induced for the complex. The strong
g
CPL
value of
g
CPL
= + 2.2 × 10
−3
was obtained, which may be attributed to the interaction between the hydroxyl groups in the side chain of PySer with those of
γ
-CD and it strengthens the chiral dimeric structure.
Graphic abstract</description><subject>Aqueous solutions</subject><subject>Carbonyls</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Circular polarization</subject><subject>Crystallography and Scattering Methods</subject><subject>Cyclodextrins</subject><subject>Dichroism</subject><subject>Dimers</subject><subject>Dyes</subject><subject>Excimers</subject><subject>Food Science</subject><subject>Grinding</subject><subject>Hydrophobicity</subject><subject>Hydroxyl groups</subject><subject>Luminescence</subject><subject>Organic Chemistry</subject><subject>Original Article</subject><issn>1388-3127</issn><issn>1573-1111</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp9Uctu1EAQtBBIJIEf4DRSLslhyDz9OCInPKSV4ADn0XjcszuR12Nm7FW8_5Mv4D_4JposUm70pUvdVdUtVVG84-w9Z6y6yZzVqqJMcMo4Ynp8UZxxXUnKsV4ilnVNJRfV6-I853vGRCmUPCse25DcMtg0rGSK2MMRejIs-zBCdjA6IFftt801cTubrJshhTwHl0n0ZLf2KU672AVHpjXBCKTH_cHO4QD55vcv6lY3xB4e5hRGcoWD9had4n4a4AEywaH9uUBcMslxWOYQR9KHjPiAT3Qr2aKuD-P2TfHK2yHD23_9ovjx8e57-5luvn760n7YUCdUM9O6176X0palrrX0qpGdlZVWDkoPnCnGLdOecdepRnVCirLyolS-qrVi3lt5UVyefKcU8bE8m_u4pBFPGlHyRuuqEQ2yxInlUsw5gTdTCnubVsOZ-RuHOcVhMA7zFIc5okieRBnJ4xbSs_V_VH8AIqOTAA</recordid><startdate>20220201</startdate><enddate>20220201</enddate><creator>Sawai, Mika</creator><creator>Matsumoto, Sayaka</creator><creator>Mimura, Yuki</creator><creator>Imai, Yoshitane</creator><creator>Yamazaki, Shoko</creator><creator>Kanehisa, Nobuko</creator><creator>Tohnai, Norimitsu</creator><creator>Nakata, Eiji</creator><creator>Takashima, Hiroshi</creator><general>Springer Netherlands</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-6875-8254</orcidid></search><sort><creationdate>20220201</creationdate><title>Circularly polarized luminescence (CPL) characteristics of hydrophobic pyrene derivatives/γ-cyclodextrin (γ-CD) complexes in aqueous solution dissolved by grinding</title><author>Sawai, Mika ; Matsumoto, Sayaka ; Mimura, Yuki ; Imai, Yoshitane ; Yamazaki, Shoko ; Kanehisa, Nobuko ; Tohnai, Norimitsu ; Nakata, Eiji ; Takashima, Hiroshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c249t-8d5fd33a665853f493ba3754ce6fe10401a05f01cb494b23267f264f78540ffa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Aqueous solutions</topic><topic>Carbonyls</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Circular polarization</topic><topic>Crystallography and Scattering Methods</topic><topic>Cyclodextrins</topic><topic>Dichroism</topic><topic>Dimers</topic><topic>Dyes</topic><topic>Excimers</topic><topic>Food Science</topic><topic>Grinding</topic><topic>Hydrophobicity</topic><topic>Hydroxyl groups</topic><topic>Luminescence</topic><topic>Organic Chemistry</topic><topic>Original Article</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sawai, Mika</creatorcontrib><creatorcontrib>Matsumoto, Sayaka</creatorcontrib><creatorcontrib>Mimura, Yuki</creatorcontrib><creatorcontrib>Imai, Yoshitane</creatorcontrib><creatorcontrib>Yamazaki, Shoko</creatorcontrib><creatorcontrib>Kanehisa, Nobuko</creatorcontrib><creatorcontrib>Tohnai, Norimitsu</creatorcontrib><creatorcontrib>Nakata, Eiji</creatorcontrib><creatorcontrib>Takashima, Hiroshi</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of inclusion phenomena and macrocyclic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sawai, Mika</au><au>Matsumoto, Sayaka</au><au>Mimura, Yuki</au><au>Imai, Yoshitane</au><au>Yamazaki, Shoko</au><au>Kanehisa, Nobuko</au><au>Tohnai, Norimitsu</au><au>Nakata, Eiji</au><au>Takashima, Hiroshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Circularly polarized luminescence (CPL) characteristics of hydrophobic pyrene derivatives/γ-cyclodextrin (γ-CD) complexes in aqueous solution dissolved by grinding</atitle><jtitle>Journal of inclusion phenomena and macrocyclic chemistry</jtitle><stitle>J Incl Phenom Macrocycl Chem</stitle><date>2022-02-01</date><risdate>2022</risdate><volume>102</volume><issue>1-2</issue><spage>133</spage><epage>142</epage><pages>133-142</pages><issn>1388-3127</issn><eissn>1573-1111</eissn><abstract>Circularly polarized luminescence (CPL) organic dyes are currently receiving a great interest, but there are still not many reported observations of CPL spectra of hydrophobic dyes from aqueous solution. We have prepared hydrophobic pyrene derivatives and dissolved them into aqueous solutions with
γ
-cyclodextrin (
γ
-CD) by using grinding technique. Among these derivatives, (pyrene-1-carbonyl)serine (PySer) forms a spatially restricted dimer in the hydrophobic chiral cavity of
γ
-CD and exhibits excimer emission with a high quantum yield of
Φ
f
= 0.68. In addition, circular dichroism and CPL signals were induced for the complex. The strong
g
CPL
value of
g
CPL
= + 2.2 × 10
−3
was obtained, which may be attributed to the interaction between the hydroxyl groups in the side chain of PySer with those of
γ
-CD and it strengthens the chiral dimeric structure.
Graphic abstract</abstract><cop>Dordrecht</cop><pub>Springer Netherlands</pub><doi>10.1007/s10847-021-01108-z</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0001-6875-8254</orcidid></addata></record> |
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| subjects | Aqueous solutions Carbonyls Chemistry Chemistry and Materials Science Circular polarization Crystallography and Scattering Methods Cyclodextrins Dichroism Dimers Dyes Excimers Food Science Grinding Hydrophobicity Hydroxyl groups Luminescence Organic Chemistry Original Article |
| title | Circularly polarized luminescence (CPL) characteristics of hydrophobic pyrene derivatives/γ-cyclodextrin (γ-CD) complexes in aqueous solution dissolved by grinding |
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