Synthesis and Characterization of Bola‐Amphiphilic Porphyrin‐Perylenebisimide Architectures
We report on the synthesis and characterization of a family of three water‐soluble bola‐amphiphilic zinc‐porphyrin‐perylenebisimide triads containing oligo carboxylic‐acid capped Newkome dendrons in the periphery. Variations of the perylenebisimide (PBI) core geometry and dendron size (G1 and G2 den...
Gespeichert in:
| Veröffentlicht in: | Chemistry : a European journal 2024-02, Vol.30 (11), p.e202303515-n/a |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | n/a |
|---|---|
| container_issue | 11 |
| container_start_page | e202303515 |
| container_title | Chemistry : a European journal |
| container_volume | 30 |
| creator | Schulze, Erik J. Ritterhoff, Christian L. Franz, Evanie Tavlui, Olha Brummel, Olaf Meyer, Bernd Hirsch, Andreas |
| description | We report on the synthesis and characterization of a family of three water‐soluble bola‐amphiphilic zinc‐porphyrin‐perylenebisimide triads containing oligo carboxylic‐acid capped Newkome dendrons in the periphery. Variations of the perylenebisimide (PBI) core geometry and dendron size (G1 and G2 dendrons with 3‐ and 9‐carboxylic acid groups respectively) allow for tuning the supramolecular aggregation behavior with respect to variation of the molecular architecture. The triads show good solubility in basic aqueous media and aggregation to supramolecular assemblies. Theoretical investigations at the DFT level of theory accompanied by electrochemical measurements unravel the geometric and electronic structure of the amphiphiles. UV/Vis and fluorescence titrations with varying amounts of THF demonstrate disaggregation.
We report the synthetic approach and the characterization of a family of highly water‐soluble porphyrin‐PBI donor‐acceptor amphiphiles by the utilization of oligo‐carboxylic acid capped Newkome dendrons. The amphiphiles form stable aggregates in basic aqueous solutions. The amphiphiles can be individualized by the addition of THF, which manifests itself, for example, in the reinstatement of fluorescence emission. |
| doi_str_mv | 10.1002/chem.202303515 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2913444955</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2913444955</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4135-7c132d1b3d4dcf442e7cf1c7e75728d513385bb79f26c6478188f83df555ed193</originalsourceid><addsrcrecordid>eNqFkMtq3DAUQEVpSaaTbLsshm6y8VRPS1pOhqQJTOlAm7WwpWus4MdEsgnOKp-Qb8yXxMNMptBNQXBBnHu4HIS-ELwgGNPvtoJmQTFlmAkiPqAZEZSkTGbiI5phzWWaCaZP0ecY7zHGOmPsBJ0yRTHOBJ0h83ts-wqij0neumRV5SG3PQT_lPe-a5OuTC67On99flk228pPr_Y22XRhW43Bt9P_BsJYQwuFj77xDpJlsJXvwfZDgHiGPpV5HeH8MOfo7vrqz-omXf_6cbtarlPLCROptIRRRwrmuLMl5xSkLYmVIIWkygnCmBJFIXVJM5txqYhSpWKuFEKAI5rN0cXeuw3dwwCxN42PFuo6b6EboqGaMM65FmJCv_2D3ndDaKfrJopqpZgk2UQt9pQNXYwBSrMNvsnDaAg2u_Rml94c008LXw_aoWjAHfH31hOg98Cjr2H8j86sbq5-_pW_AY0uknA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2929883716</pqid></control><display><type>article</type><title>Synthesis and Characterization of Bola‐Amphiphilic Porphyrin‐Perylenebisimide Architectures</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Schulze, Erik J. ; Ritterhoff, Christian L. ; Franz, Evanie ; Tavlui, Olha ; Brummel, Olaf ; Meyer, Bernd ; Hirsch, Andreas</creator><creatorcontrib>Schulze, Erik J. ; Ritterhoff, Christian L. ; Franz, Evanie ; Tavlui, Olha ; Brummel, Olaf ; Meyer, Bernd ; Hirsch, Andreas</creatorcontrib><description>We report on the synthesis and characterization of a family of three water‐soluble bola‐amphiphilic zinc‐porphyrin‐perylenebisimide triads containing oligo carboxylic‐acid capped Newkome dendrons in the periphery. Variations of the perylenebisimide (PBI) core geometry and dendron size (G1 and G2 dendrons with 3‐ and 9‐carboxylic acid groups respectively) allow for tuning the supramolecular aggregation behavior with respect to variation of the molecular architecture. The triads show good solubility in basic aqueous media and aggregation to supramolecular assemblies. Theoretical investigations at the DFT level of theory accompanied by electrochemical measurements unravel the geometric and electronic structure of the amphiphiles. UV/Vis and fluorescence titrations with varying amounts of THF demonstrate disaggregation.
We report the synthetic approach and the characterization of a family of highly water‐soluble porphyrin‐PBI donor‐acceptor amphiphiles by the utilization of oligo‐carboxylic acid capped Newkome dendrons. The amphiphiles form stable aggregates in basic aqueous solutions. The amphiphiles can be individualized by the addition of THF, which manifests itself, for example, in the reinstatement of fluorescence emission.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202303515</identifier><identifier>PMID: 38200652</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Aggregation ; Aggregation behavior ; Amphiphiles ; Aqueous solutions ; Carboxylic acids ; Disaggregation ; Donor-Acceptor-Hybrids ; Electrochemistry ; Electronic structure ; Molecular structure ; Perylenebisimide ; Porphyrinoids ; Porphyrins ; Synthesis</subject><ispartof>Chemistry : a European journal, 2024-02, Vol.30 (11), p.e202303515-n/a</ispartof><rights>2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH</rights><rights>2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.</rights><rights>2024. This article is published under http://creativecommons.org/licenses/by-nc/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4135-7c132d1b3d4dcf442e7cf1c7e75728d513385bb79f26c6478188f83df555ed193</citedby><cites>FETCH-LOGICAL-c4135-7c132d1b3d4dcf442e7cf1c7e75728d513385bb79f26c6478188f83df555ed193</cites><orcidid>0000-0002-3481-8009 ; 0000-0003-1458-8872</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.202303515$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.202303515$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38200652$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Schulze, Erik J.</creatorcontrib><creatorcontrib>Ritterhoff, Christian L.</creatorcontrib><creatorcontrib>Franz, Evanie</creatorcontrib><creatorcontrib>Tavlui, Olha</creatorcontrib><creatorcontrib>Brummel, Olaf</creatorcontrib><creatorcontrib>Meyer, Bernd</creatorcontrib><creatorcontrib>Hirsch, Andreas</creatorcontrib><title>Synthesis and Characterization of Bola‐Amphiphilic Porphyrin‐Perylenebisimide Architectures</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>We report on the synthesis and characterization of a family of three water‐soluble bola‐amphiphilic zinc‐porphyrin‐perylenebisimide triads containing oligo carboxylic‐acid capped Newkome dendrons in the periphery. Variations of the perylenebisimide (PBI) core geometry and dendron size (G1 and G2 dendrons with 3‐ and 9‐carboxylic acid groups respectively) allow for tuning the supramolecular aggregation behavior with respect to variation of the molecular architecture. The triads show good solubility in basic aqueous media and aggregation to supramolecular assemblies. Theoretical investigations at the DFT level of theory accompanied by electrochemical measurements unravel the geometric and electronic structure of the amphiphiles. UV/Vis and fluorescence titrations with varying amounts of THF demonstrate disaggregation.
We report the synthetic approach and the characterization of a family of highly water‐soluble porphyrin‐PBI donor‐acceptor amphiphiles by the utilization of oligo‐carboxylic acid capped Newkome dendrons. The amphiphiles form stable aggregates in basic aqueous solutions. The amphiphiles can be individualized by the addition of THF, which manifests itself, for example, in the reinstatement of fluorescence emission.</description><subject>Aggregation</subject><subject>Aggregation behavior</subject><subject>Amphiphiles</subject><subject>Aqueous solutions</subject><subject>Carboxylic acids</subject><subject>Disaggregation</subject><subject>Donor-Acceptor-Hybrids</subject><subject>Electrochemistry</subject><subject>Electronic structure</subject><subject>Molecular structure</subject><subject>Perylenebisimide</subject><subject>Porphyrinoids</subject><subject>Porphyrins</subject><subject>Synthesis</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqFkMtq3DAUQEVpSaaTbLsshm6y8VRPS1pOhqQJTOlAm7WwpWus4MdEsgnOKp-Qb8yXxMNMptBNQXBBnHu4HIS-ELwgGNPvtoJmQTFlmAkiPqAZEZSkTGbiI5phzWWaCaZP0ecY7zHGOmPsBJ0yRTHOBJ0h83ts-wqij0neumRV5SG3PQT_lPe-a5OuTC67On99flk228pPr_Y22XRhW43Bt9P_BsJYQwuFj77xDpJlsJXvwfZDgHiGPpV5HeH8MOfo7vrqz-omXf_6cbtarlPLCROptIRRRwrmuLMl5xSkLYmVIIWkygnCmBJFIXVJM5txqYhSpWKuFEKAI5rN0cXeuw3dwwCxN42PFuo6b6EboqGaMM65FmJCv_2D3ndDaKfrJopqpZgk2UQt9pQNXYwBSrMNvsnDaAg2u_Rml94c008LXw_aoWjAHfH31hOg98Cjr2H8j86sbq5-_pW_AY0uknA</recordid><startdate>20240221</startdate><enddate>20240221</enddate><creator>Schulze, Erik J.</creator><creator>Ritterhoff, Christian L.</creator><creator>Franz, Evanie</creator><creator>Tavlui, Olha</creator><creator>Brummel, Olaf</creator><creator>Meyer, Bernd</creator><creator>Hirsch, Andreas</creator><general>Wiley Subscription Services, Inc</general><scope>24P</scope><scope>WIN</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3481-8009</orcidid><orcidid>https://orcid.org/0000-0003-1458-8872</orcidid></search><sort><creationdate>20240221</creationdate><title>Synthesis and Characterization of Bola‐Amphiphilic Porphyrin‐Perylenebisimide Architectures</title><author>Schulze, Erik J. ; Ritterhoff, Christian L. ; Franz, Evanie ; Tavlui, Olha ; Brummel, Olaf ; Meyer, Bernd ; Hirsch, Andreas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4135-7c132d1b3d4dcf442e7cf1c7e75728d513385bb79f26c6478188f83df555ed193</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Aggregation</topic><topic>Aggregation behavior</topic><topic>Amphiphiles</topic><topic>Aqueous solutions</topic><topic>Carboxylic acids</topic><topic>Disaggregation</topic><topic>Donor-Acceptor-Hybrids</topic><topic>Electrochemistry</topic><topic>Electronic structure</topic><topic>Molecular structure</topic><topic>Perylenebisimide</topic><topic>Porphyrinoids</topic><topic>Porphyrins</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Schulze, Erik J.</creatorcontrib><creatorcontrib>Ritterhoff, Christian L.</creatorcontrib><creatorcontrib>Franz, Evanie</creatorcontrib><creatorcontrib>Tavlui, Olha</creatorcontrib><creatorcontrib>Brummel, Olaf</creatorcontrib><creatorcontrib>Meyer, Bernd</creatorcontrib><creatorcontrib>Hirsch, Andreas</creatorcontrib><collection>Wiley Online Library Open Access</collection><collection>Wiley Free Content</collection><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>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Schulze, Erik J.</au><au>Ritterhoff, Christian L.</au><au>Franz, Evanie</au><au>Tavlui, Olha</au><au>Brummel, Olaf</au><au>Meyer, Bernd</au><au>Hirsch, Andreas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Characterization of Bola‐Amphiphilic Porphyrin‐Perylenebisimide Architectures</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2024-02-21</date><risdate>2024</risdate><volume>30</volume><issue>11</issue><spage>e202303515</spage><epage>n/a</epage><pages>e202303515-n/a</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>We report on the synthesis and characterization of a family of three water‐soluble bola‐amphiphilic zinc‐porphyrin‐perylenebisimide triads containing oligo carboxylic‐acid capped Newkome dendrons in the periphery. Variations of the perylenebisimide (PBI) core geometry and dendron size (G1 and G2 dendrons with 3‐ and 9‐carboxylic acid groups respectively) allow for tuning the supramolecular aggregation behavior with respect to variation of the molecular architecture. The triads show good solubility in basic aqueous media and aggregation to supramolecular assemblies. Theoretical investigations at the DFT level of theory accompanied by electrochemical measurements unravel the geometric and electronic structure of the amphiphiles. UV/Vis and fluorescence titrations with varying amounts of THF demonstrate disaggregation.
We report the synthetic approach and the characterization of a family of highly water‐soluble porphyrin‐PBI donor‐acceptor amphiphiles by the utilization of oligo‐carboxylic acid capped Newkome dendrons. The amphiphiles form stable aggregates in basic aqueous solutions. The amphiphiles can be individualized by the addition of THF, which manifests itself, for example, in the reinstatement of fluorescence emission.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>38200652</pmid><doi>10.1002/chem.202303515</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-3481-8009</orcidid><orcidid>https://orcid.org/0000-0003-1458-8872</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0947-6539 |
| ispartof | Chemistry : a European journal, 2024-02, Vol.30 (11), p.e202303515-n/a |
| issn | 0947-6539 1521-3765 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2913444955 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Aggregation Aggregation behavior Amphiphiles Aqueous solutions Carboxylic acids Disaggregation Donor-Acceptor-Hybrids Electrochemistry Electronic structure Molecular structure Perylenebisimide Porphyrinoids Porphyrins Synthesis |
| title | Synthesis and Characterization of Bola‐Amphiphilic Porphyrin‐Perylenebisimide Architectures |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-23T05%3A05%3A49IST&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=Synthesis%20and%20Characterization%20of%20Bola%E2%80%90Amphiphilic%20Porphyrin%E2%80%90Perylenebisimide%20Architectures&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Schulze,%20Erik%20J.&rft.date=2024-02-21&rft.volume=30&rft.issue=11&rft.spage=e202303515&rft.epage=n/a&rft.pages=e202303515-n/a&rft.issn=0947-6539&rft.eissn=1521-3765&rft_id=info:doi/10.1002/chem.202303515&rft_dat=%3Cproquest_cross%3E2913444955%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=2929883716&rft_id=info:pmid/38200652&rfr_iscdi=true |