Trimeric Assembly of Dendritic Light-Harvesting Antenna with Two Kinds of Porphyrin Cores
A trimeric assembly of light-harvesting antennas was prepared using a copper-catalyzed Hüisgen 1,3-dipolar cycloaddition reaction between a dendrimer having a zinc diethynyldiphenylporphyrin core (ZnDEDPP) with two azide terminals and two equivalents of dendrimers having a zinc tetraphenylporphyrin...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2017-09, Vol.82 (17), p.8917-8926 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 8926 |
|---|---|
| container_issue | 17 |
| container_start_page | 8917 |
| container_title | Journal of organic chemistry |
| container_volume | 82 |
| creator | Kimura, Ryo Suzuki, Shuichi Okada, Keiji Kozaki, Masatoshi |
| description | A trimeric assembly of light-harvesting antennas was prepared using a copper-catalyzed Hüisgen 1,3-dipolar cycloaddition reaction between a dendrimer having a zinc diethynyldiphenylporphyrin core (ZnDEDPP) with two azide terminals and two equivalents of dendrimers having a zinc tetraphenylporphyrin core (ZnTPP) with one ethynyl terminal. The absorptions of the trimer appear in a longer-wavelength region compared to monomeric references in toluene; however, there is almost no shift in wavelength in 1,1,2,2-tetrachloroethane (TCE). Fluorescence spectra of the trimer show that the singlet energy transfer from ZnTPP to ZnDEDPP takes place more effectively in toluene than in TCE. These absorption and fluorescence studies are compatible with solvent-dependent conformation; the extended forms of the trimers are favored by solvation in polar TCE, and the folded conformation is stabilized by the attractive van der Waals and dipole–dipole interactions between the dendritic chains in nonpolar toluene. |
| doi_str_mv | 10.1021/acs.joc.7b01275 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1926979904</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1926979904</sourcerecordid><originalsourceid>FETCH-LOGICAL-a333t-e9495ea09654ceb9f1af5be43e08ced49c8d65bf72b86d7fc97e419fcc69f8153</originalsourceid><addsrcrecordid>eNp1kD1PwzAURS0EoqUwsyGPSCjFduIkHqvyUUQlGMrAFDnOc-sqdYqdUPXf4yqFDS9Pss69eu8gdE3JmBJG76Xy43WjxllJKMv4CRpSzkiUCpKcoiEhjEUxS-MBuvB-TcLjnJ-jAcuznMUpHaLPhTMbcEbhifewKes9bjR-AFs504bfuVmu2mgm3Tf41tglntgWrJV4Z9oVXuwa_Gps5Q-h98ZtV3tnLJ42DvwlOtOy9nB1nCP08fS4mM6i-dvzy3Qyj2Qcx20EIhEcJBEpTxSUQlOpeQlJDCRXUCVC5VXKS52xMk-rTCuRQUKFVioVOqc8HqHbvnfrmq8ubFlsjFdQ19JC0_mCCpaKTAQjAb3vUeUa7x3oYhuul25fUFIcfBbBZxF8FkefIXFzLO_KDVR__K_AANz1QJ_snA23_lv3A2EzgXk</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1926979904</pqid></control><display><type>article</type><title>Trimeric Assembly of Dendritic Light-Harvesting Antenna with Two Kinds of Porphyrin Cores</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Kimura, Ryo ; Suzuki, Shuichi ; Okada, Keiji ; Kozaki, Masatoshi</creator><creatorcontrib>Kimura, Ryo ; Suzuki, Shuichi ; Okada, Keiji ; Kozaki, Masatoshi</creatorcontrib><description>A trimeric assembly of light-harvesting antennas was prepared using a copper-catalyzed Hüisgen 1,3-dipolar cycloaddition reaction between a dendrimer having a zinc diethynyldiphenylporphyrin core (ZnDEDPP) with two azide terminals and two equivalents of dendrimers having a zinc tetraphenylporphyrin core (ZnTPP) with one ethynyl terminal. The absorptions of the trimer appear in a longer-wavelength region compared to monomeric references in toluene; however, there is almost no shift in wavelength in 1,1,2,2-tetrachloroethane (TCE). Fluorescence spectra of the trimer show that the singlet energy transfer from ZnTPP to ZnDEDPP takes place more effectively in toluene than in TCE. These absorption and fluorescence studies are compatible with solvent-dependent conformation; the extended forms of the trimers are favored by solvation in polar TCE, and the folded conformation is stabilized by the attractive van der Waals and dipole–dipole interactions between the dendritic chains in nonpolar toluene.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.7b01275</identifier><identifier>PMID: 28782361</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkynes - chemistry ; Azides - chemistry ; Catalysis ; Copper - chemistry ; Cycloaddition Reaction ; Dendrimers - chemical synthesis ; Dendrimers - chemistry ; Light-Harvesting Protein Complexes - chemistry ; Light-Harvesting Protein Complexes - metabolism ; Metalloporphyrins - chemistry ; Molecular Structure</subject><ispartof>Journal of organic chemistry, 2017-09, Vol.82 (17), p.8917-8926</ispartof><rights>Copyright © 2017 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-e9495ea09654ceb9f1af5be43e08ced49c8d65bf72b86d7fc97e419fcc69f8153</citedby><cites>FETCH-LOGICAL-a333t-e9495ea09654ceb9f1af5be43e08ced49c8d65bf72b86d7fc97e419fcc69f8153</cites><orcidid>0000-0002-9737-5639 ; 0000-0002-2817-9335</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.7b01275$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.7b01275$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27078,27926,27927,56740,56790</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28782361$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kimura, Ryo</creatorcontrib><creatorcontrib>Suzuki, Shuichi</creatorcontrib><creatorcontrib>Okada, Keiji</creatorcontrib><creatorcontrib>Kozaki, Masatoshi</creatorcontrib><title>Trimeric Assembly of Dendritic Light-Harvesting Antenna with Two Kinds of Porphyrin Cores</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A trimeric assembly of light-harvesting antennas was prepared using a copper-catalyzed Hüisgen 1,3-dipolar cycloaddition reaction between a dendrimer having a zinc diethynyldiphenylporphyrin core (ZnDEDPP) with two azide terminals and two equivalents of dendrimers having a zinc tetraphenylporphyrin core (ZnTPP) with one ethynyl terminal. The absorptions of the trimer appear in a longer-wavelength region compared to monomeric references in toluene; however, there is almost no shift in wavelength in 1,1,2,2-tetrachloroethane (TCE). Fluorescence spectra of the trimer show that the singlet energy transfer from ZnTPP to ZnDEDPP takes place more effectively in toluene than in TCE. These absorption and fluorescence studies are compatible with solvent-dependent conformation; the extended forms of the trimers are favored by solvation in polar TCE, and the folded conformation is stabilized by the attractive van der Waals and dipole–dipole interactions between the dendritic chains in nonpolar toluene.</description><subject>Alkynes - chemistry</subject><subject>Azides - chemistry</subject><subject>Catalysis</subject><subject>Copper - chemistry</subject><subject>Cycloaddition Reaction</subject><subject>Dendrimers - chemical synthesis</subject><subject>Dendrimers - chemistry</subject><subject>Light-Harvesting Protein Complexes - chemistry</subject><subject>Light-Harvesting Protein Complexes - metabolism</subject><subject>Metalloporphyrins - chemistry</subject><subject>Molecular Structure</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kD1PwzAURS0EoqUwsyGPSCjFduIkHqvyUUQlGMrAFDnOc-sqdYqdUPXf4yqFDS9Pss69eu8gdE3JmBJG76Xy43WjxllJKMv4CRpSzkiUCpKcoiEhjEUxS-MBuvB-TcLjnJ-jAcuznMUpHaLPhTMbcEbhifewKes9bjR-AFs504bfuVmu2mgm3Tf41tglntgWrJV4Z9oVXuwa_Gps5Q-h98ZtV3tnLJ42DvwlOtOy9nB1nCP08fS4mM6i-dvzy3Qyj2Qcx20EIhEcJBEpTxSUQlOpeQlJDCRXUCVC5VXKS52xMk-rTCuRQUKFVioVOqc8HqHbvnfrmq8ubFlsjFdQ19JC0_mCCpaKTAQjAb3vUeUa7x3oYhuul25fUFIcfBbBZxF8FkefIXFzLO_KDVR__K_AANz1QJ_snA23_lv3A2EzgXk</recordid><startdate>20170901</startdate><enddate>20170901</enddate><creator>Kimura, Ryo</creator><creator>Suzuki, Shuichi</creator><creator>Okada, Keiji</creator><creator>Kozaki, Masatoshi</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-9737-5639</orcidid><orcidid>https://orcid.org/0000-0002-2817-9335</orcidid></search><sort><creationdate>20170901</creationdate><title>Trimeric Assembly of Dendritic Light-Harvesting Antenna with Two Kinds of Porphyrin Cores</title><author>Kimura, Ryo ; Suzuki, Shuichi ; Okada, Keiji ; Kozaki, Masatoshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-e9495ea09654ceb9f1af5be43e08ced49c8d65bf72b86d7fc97e419fcc69f8153</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Alkynes - chemistry</topic><topic>Azides - chemistry</topic><topic>Catalysis</topic><topic>Copper - chemistry</topic><topic>Cycloaddition Reaction</topic><topic>Dendrimers - chemical synthesis</topic><topic>Dendrimers - chemistry</topic><topic>Light-Harvesting Protein Complexes - chemistry</topic><topic>Light-Harvesting Protein Complexes - metabolism</topic><topic>Metalloporphyrins - chemistry</topic><topic>Molecular Structure</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kimura, Ryo</creatorcontrib><creatorcontrib>Suzuki, Shuichi</creatorcontrib><creatorcontrib>Okada, Keiji</creatorcontrib><creatorcontrib>Kozaki, Masatoshi</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kimura, Ryo</au><au>Suzuki, Shuichi</au><au>Okada, Keiji</au><au>Kozaki, Masatoshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Trimeric Assembly of Dendritic Light-Harvesting Antenna with Two Kinds of Porphyrin Cores</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2017-09-01</date><risdate>2017</risdate><volume>82</volume><issue>17</issue><spage>8917</spage><epage>8926</epage><pages>8917-8926</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A trimeric assembly of light-harvesting antennas was prepared using a copper-catalyzed Hüisgen 1,3-dipolar cycloaddition reaction between a dendrimer having a zinc diethynyldiphenylporphyrin core (ZnDEDPP) with two azide terminals and two equivalents of dendrimers having a zinc tetraphenylporphyrin core (ZnTPP) with one ethynyl terminal. The absorptions of the trimer appear in a longer-wavelength region compared to monomeric references in toluene; however, there is almost no shift in wavelength in 1,1,2,2-tetrachloroethane (TCE). Fluorescence spectra of the trimer show that the singlet energy transfer from ZnTPP to ZnDEDPP takes place more effectively in toluene than in TCE. These absorption and fluorescence studies are compatible with solvent-dependent conformation; the extended forms of the trimers are favored by solvation in polar TCE, and the folded conformation is stabilized by the attractive van der Waals and dipole–dipole interactions between the dendritic chains in nonpolar toluene.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>28782361</pmid><doi>10.1021/acs.joc.7b01275</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-9737-5639</orcidid><orcidid>https://orcid.org/0000-0002-2817-9335</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2017-09, Vol.82 (17), p.8917-8926 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1926979904 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Alkynes - chemistry Azides - chemistry Catalysis Copper - chemistry Cycloaddition Reaction Dendrimers - chemical synthesis Dendrimers - chemistry Light-Harvesting Protein Complexes - chemistry Light-Harvesting Protein Complexes - metabolism Metalloporphyrins - chemistry Molecular Structure |
| title | Trimeric Assembly of Dendritic Light-Harvesting Antenna with Two Kinds of Porphyrin Cores |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-18T03%3A56%3A41IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Trimeric%20Assembly%20of%20Dendritic%20Light-Harvesting%20Antenna%20with%20Two%20Kinds%20of%20Porphyrin%20Cores&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Kimura,%20Ryo&rft.date=2017-09-01&rft.volume=82&rft.issue=17&rft.spage=8917&rft.epage=8926&rft.pages=8917-8926&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.7b01275&rft_dat=%3Cproquest_cross%3E1926979904%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1926979904&rft_id=info:pmid/28782361&rfr_iscdi=true |