Flavin‐Helicene Amphiphilic Hybrids: Synthesis, Characterization, and Preparation of Surface‐Supported Films
This work reports on the preparation and structural characterization of flavo[7]helicene 1 (flavin‐[7]helicene conjugate), which was subsequently characterized at the molecular level in either an aqueous environment or an organic phase, at the supramolecular level in the form of polymeric layers, an...
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| Veröffentlicht in: | ChemPlusChem (Weinheim, Germany) Germany), 2021-07, Vol.86 (7), p.982-990 |
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| creator | Jakubec, Martin Novák, David Zatloukalová, Martina Císařová, Ivana Cibulka, Radek Favereau, Ludovic Crassous, Jeanne Cytryniak, Adrianna Bilewicz, Renata Hrbáč, Jan Storch, Jan Žádný, Jaroslav Vacek, Jan |
| description | This work reports on the preparation and structural characterization of flavo[7]helicene 1 (flavin‐[7]helicene conjugate), which was subsequently characterized at the molecular level in either an aqueous environment or an organic phase, at the supramolecular level in the form of polymeric layers, and also embedded in a lipidic mesophase environment to study the resulting properties of such a hybrid relative to its parent molecules. The flavin benzo[g]pteridin‐2,4‐dione (isoalloxazine) was selected for conjugation because of its photoactivity and reversible redox behavior. Compound 1 was prepared from 2‐nitroso[6]helicene and 6‐methylamino‐3‐methyluracil, and characterized using common structural and spectroscopic tools: circular dichroism (CD), circularly polarized luminescence (CPL) spectroscopy, cyclic voltammetry (CV), and DFT quantum calculations. In addition, a methodology that allows the loading of 1 enantiomers into an internally nanostructured lipid (1‐monoolein) matrix was developed.
The complex characterization of a flavo[7]helicene conjugate is reported in this work. This conjugate combines inherent helical chirality with redox activity, which was studied in solution (both aqueous and organic phases), in layers (electropolymers), and in the solid state (a single crystal). |
| doi_str_mv | 10.1002/cplu.202100092 |
| format | Article |
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The complex characterization of a flavo[7]helicene conjugate is reported in this work. This conjugate combines inherent helical chirality with redox activity, which was studied in solution (both aqueous and organic phases), in layers (electropolymers), and in the solid state (a single crystal).</description><identifier>ISSN: 2192-6506</identifier><identifier>EISSN: 2192-6506</identifier><identifier>DOI: 10.1002/cplu.202100092</identifier><identifier>PMID: 33977667</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Aqueous environments ; Chemical Sciences ; Chemistry ; Circular polarization ; Conjugation ; Dichroism ; Enantiomers ; flavins ; helicenes ; Hybrids ; lipidic cubic phases ; Lipids ; or physical chemistry ; Organic chemistry ; redox behavior ; Structural analysis ; Theoretical and ; thin layers</subject><ispartof>ChemPlusChem (Weinheim, Germany), 2021-07, Vol.86 (7), p.982-990</ispartof><rights>2021 Wiley‐VCH GmbH</rights><rights>2021 Wiley-VCH GmbH.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4472-2722b111b5156bd0272db2d714bbd9bab04140ecd86fcb76ad389ca2d15ca17c3</citedby><cites>FETCH-LOGICAL-c4472-2722b111b5156bd0272db2d714bbd9bab04140ecd86fcb76ad389ca2d15ca17c3</cites><orcidid>0000-0001-5490-082X ; 0000-0002-4037-6067 ; 0000-0002-0877-5906</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%2Fcplu.202100092$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcplu.202100092$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,780,784,885,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33977667$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-03245189$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Jakubec, Martin</creatorcontrib><creatorcontrib>Novák, David</creatorcontrib><creatorcontrib>Zatloukalová, Martina</creatorcontrib><creatorcontrib>Císařová, Ivana</creatorcontrib><creatorcontrib>Cibulka, Radek</creatorcontrib><creatorcontrib>Favereau, Ludovic</creatorcontrib><creatorcontrib>Crassous, Jeanne</creatorcontrib><creatorcontrib>Cytryniak, Adrianna</creatorcontrib><creatorcontrib>Bilewicz, Renata</creatorcontrib><creatorcontrib>Hrbáč, Jan</creatorcontrib><creatorcontrib>Storch, Jan</creatorcontrib><creatorcontrib>Žádný, Jaroslav</creatorcontrib><creatorcontrib>Vacek, Jan</creatorcontrib><title>Flavin‐Helicene Amphiphilic Hybrids: Synthesis, Characterization, and Preparation of Surface‐Supported Films</title><title>ChemPlusChem (Weinheim, Germany)</title><addtitle>Chempluschem</addtitle><description>This work reports on the preparation and structural characterization of flavo[7]helicene 1 (flavin‐[7]helicene conjugate), which was subsequently characterized at the molecular level in either an aqueous environment or an organic phase, at the supramolecular level in the form of polymeric layers, and also embedded in a lipidic mesophase environment to study the resulting properties of such a hybrid relative to its parent molecules. The flavin benzo[g]pteridin‐2,4‐dione (isoalloxazine) was selected for conjugation because of its photoactivity and reversible redox behavior. Compound 1 was prepared from 2‐nitroso[6]helicene and 6‐methylamino‐3‐methyluracil, and characterized using common structural and spectroscopic tools: circular dichroism (CD), circularly polarized luminescence (CPL) spectroscopy, cyclic voltammetry (CV), and DFT quantum calculations. In addition, a methodology that allows the loading of 1 enantiomers into an internally nanostructured lipid (1‐monoolein) matrix was developed.
The complex characterization of a flavo[7]helicene conjugate is reported in this work. This conjugate combines inherent helical chirality with redox activity, which was studied in solution (both aqueous and organic phases), in layers (electropolymers), and in the solid state (a single crystal).</description><subject>Aqueous environments</subject><subject>Chemical Sciences</subject><subject>Chemistry</subject><subject>Circular polarization</subject><subject>Conjugation</subject><subject>Dichroism</subject><subject>Enantiomers</subject><subject>flavins</subject><subject>helicenes</subject><subject>Hybrids</subject><subject>lipidic cubic phases</subject><subject>Lipids</subject><subject>or physical chemistry</subject><subject>Organic chemistry</subject><subject>redox behavior</subject><subject>Structural analysis</subject><subject>Theoretical and</subject><subject>thin layers</subject><issn>2192-6506</issn><issn>2192-6506</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkV1rFDEYhYMottTeeikBbxS6a_LOJNnxbllcV1iwsPY65GvYlMyHyUzLeuVP6G_sLzHD1lW8EQLJOTw5vMlB6DUlc0oIfDB9GOdAIAtSwTN0DrSCGWeEP__rfIYuU7rNCOGEgSheorOiqITgXJyjfh3UnW8ffz5sXPDGtQ4vm37v88oSbw46eps-4t2hHfYu-XSFV3sVlRlc9D_U4Lv2CqvW4uvo-uxPBu5qvBtjrYzLubux77s4OIvXPjTpFXpRq5Dc5dN-gW7Wn76tNrPt189fVsvtzJSlgBkIAE0p1Ywyri3J2mqwgpZa20orTUpaEmfsgtdGC65ssaiMAkuZUVSY4gK9P-buVZB99I2KB9kpLzfLrZw8UkDJ6KK6o5l9d2T72H0fXRpk45NxIajWdWOSwIDTMv8Zz-jbf9DbboxtfkmmmICKsGKi5kfKxC6l6OrTBJTIqTo5VSdP1eULb55iR904e8J_F5WB6gjc--AO_4mTq-vtzZ_wX4IZpuA</recordid><startdate>202107</startdate><enddate>202107</enddate><creator>Jakubec, Martin</creator><creator>Novák, David</creator><creator>Zatloukalová, Martina</creator><creator>Císařová, Ivana</creator><creator>Cibulka, Radek</creator><creator>Favereau, Ludovic</creator><creator>Crassous, Jeanne</creator><creator>Cytryniak, Adrianna</creator><creator>Bilewicz, Renata</creator><creator>Hrbáč, Jan</creator><creator>Storch, Jan</creator><creator>Žádný, Jaroslav</creator><creator>Vacek, Jan</creator><general>Blackwell Publishing Ltd</general><general>Wiley</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>4T-</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0001-5490-082X</orcidid><orcidid>https://orcid.org/0000-0002-4037-6067</orcidid><orcidid>https://orcid.org/0000-0002-0877-5906</orcidid></search><sort><creationdate>202107</creationdate><title>Flavin‐Helicene Amphiphilic Hybrids: Synthesis, Characterization, and Preparation of Surface‐Supported Films</title><author>Jakubec, Martin ; Novák, David ; Zatloukalová, Martina ; Císařová, Ivana ; Cibulka, Radek ; Favereau, Ludovic ; Crassous, Jeanne ; Cytryniak, Adrianna ; Bilewicz, Renata ; Hrbáč, Jan ; Storch, Jan ; Žádný, Jaroslav ; Vacek, Jan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4472-2722b111b5156bd0272db2d714bbd9bab04140ecd86fcb76ad389ca2d15ca17c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aqueous environments</topic><topic>Chemical Sciences</topic><topic>Chemistry</topic><topic>Circular polarization</topic><topic>Conjugation</topic><topic>Dichroism</topic><topic>Enantiomers</topic><topic>flavins</topic><topic>helicenes</topic><topic>Hybrids</topic><topic>lipidic cubic phases</topic><topic>Lipids</topic><topic>or physical chemistry</topic><topic>Organic chemistry</topic><topic>redox behavior</topic><topic>Structural analysis</topic><topic>Theoretical and</topic><topic>thin layers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jakubec, Martin</creatorcontrib><creatorcontrib>Novák, David</creatorcontrib><creatorcontrib>Zatloukalová, Martina</creatorcontrib><creatorcontrib>Císařová, Ivana</creatorcontrib><creatorcontrib>Cibulka, Radek</creatorcontrib><creatorcontrib>Favereau, Ludovic</creatorcontrib><creatorcontrib>Crassous, Jeanne</creatorcontrib><creatorcontrib>Cytryniak, Adrianna</creatorcontrib><creatorcontrib>Bilewicz, Renata</creatorcontrib><creatorcontrib>Hrbáč, Jan</creatorcontrib><creatorcontrib>Storch, Jan</creatorcontrib><creatorcontrib>Žádný, Jaroslav</creatorcontrib><creatorcontrib>Vacek, Jan</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Docstoc</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>ChemPlusChem (Weinheim, Germany)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jakubec, Martin</au><au>Novák, David</au><au>Zatloukalová, Martina</au><au>Císařová, Ivana</au><au>Cibulka, Radek</au><au>Favereau, Ludovic</au><au>Crassous, Jeanne</au><au>Cytryniak, Adrianna</au><au>Bilewicz, Renata</au><au>Hrbáč, Jan</au><au>Storch, Jan</au><au>Žádný, Jaroslav</au><au>Vacek, Jan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Flavin‐Helicene Amphiphilic Hybrids: Synthesis, Characterization, and Preparation of Surface‐Supported Films</atitle><jtitle>ChemPlusChem (Weinheim, Germany)</jtitle><addtitle>Chempluschem</addtitle><date>2021-07</date><risdate>2021</risdate><volume>86</volume><issue>7</issue><spage>982</spage><epage>990</epage><pages>982-990</pages><issn>2192-6506</issn><eissn>2192-6506</eissn><abstract>This work reports on the preparation and structural characterization of flavo[7]helicene 1 (flavin‐[7]helicene conjugate), which was subsequently characterized at the molecular level in either an aqueous environment or an organic phase, at the supramolecular level in the form of polymeric layers, and also embedded in a lipidic mesophase environment to study the resulting properties of such a hybrid relative to its parent molecules. The flavin benzo[g]pteridin‐2,4‐dione (isoalloxazine) was selected for conjugation because of its photoactivity and reversible redox behavior. Compound 1 was prepared from 2‐nitroso[6]helicene and 6‐methylamino‐3‐methyluracil, and characterized using common structural and spectroscopic tools: circular dichroism (CD), circularly polarized luminescence (CPL) spectroscopy, cyclic voltammetry (CV), and DFT quantum calculations. In addition, a methodology that allows the loading of 1 enantiomers into an internally nanostructured lipid (1‐monoolein) matrix was developed.
The complex characterization of a flavo[7]helicene conjugate is reported in this work. This conjugate combines inherent helical chirality with redox activity, which was studied in solution (both aqueous and organic phases), in layers (electropolymers), and in the solid state (a single crystal).</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>33977667</pmid><doi>10.1002/cplu.202100092</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-5490-082X</orcidid><orcidid>https://orcid.org/0000-0002-4037-6067</orcidid><orcidid>https://orcid.org/0000-0002-0877-5906</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Aqueous environments Chemical Sciences Chemistry Circular polarization Conjugation Dichroism Enantiomers flavins helicenes Hybrids lipidic cubic phases Lipids or physical chemistry Organic chemistry redox behavior Structural analysis Theoretical and thin layers |
| title | Flavin‐Helicene Amphiphilic Hybrids: Synthesis, Characterization, and Preparation of Surface‐Supported Films |
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