Discovery of an all-donor aromatic [2]catenane
We report herein the first all-donor aromatic [2]catenane formed through dynamic combinatorial chemistry, using single component libraries. The building block is a benzo[1,2- b :4,5- b ′]dithiophene derivative, a π-donor molecule, with cysteine appendages that allow for disulfide exchange. The hydro...
Gespeichert in:
| Veröffentlicht in: | Chemical science (Cambridge) 2020-09, Vol.11 (35), p.9685-969 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 969 |
|---|---|
| container_issue | 35 |
| container_start_page | 9685 |
| container_title | Chemical science (Cambridge) |
| container_volume | 11 |
| creator | Gianga, Tiberiu-M Audibert, Edwige Trandafir, Anamaria Kociok-Köhn, Gabriele Panto, G. Dan |
| description | We report herein the first all-donor aromatic [2]catenane formed through dynamic combinatorial chemistry, using single component libraries. The building block is a benzo[1,2-
b
:4,5-
b
′]dithiophene derivative, a π-donor molecule, with cysteine appendages that allow for disulfide exchange. The hydrophobic effect plays an essential role in the formation of the all-donor [2]catenane. The design of the building block allows the formation of a quasi-fused pentacyclic core, which enhances the stacking interactions between the cores. The [2]catenane has chiro-optical and fluorescent properties, being also the first known DCC-disulphide-based interlocked molecule to be fluorescent.
An all-donor [2]catenane has been synthesised
via
dynamic combinatorial chemistry. It features stacked benzodithiophenes which are quasi-pentacyclic through hydrogen bonding. |
| doi_str_mv | 10.1039/d0sc04317f |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_rsc_p</sourceid><recordid>TN_cdi_rsc_primary_d0sc04317f</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2442838799</sourcerecordid><originalsourceid>FETCH-LOGICAL-c431t-2c5106b2e3394e8b1550e4c843e14dbe6e405d3cc4dee66424a817daa91d6a063</originalsourceid><addsrcrecordid>eNp9kc1Lw0AQxRdRbKm9eBciXkRI3a8km4sgrVWh4EE9iSyb3YmmpNm6mxT637vaUtGDc5mB92OYNw-hY4JHBLP80mCvMWckK_dQn2JO4jRh-f5upriHht7PcSjGSEKzQ9RjHOecMtZHo0nltV2BW0e2jFQTqbqOjW2si5SzC9VWOnqhr1q10KgGjtBBqWoPw20foOfpzdP4Lp493N6Pr2exDqe0MdUJwWlBgbGcgyhIkmDgWnAGhJsCUuA4MUxrbgDSlFOuBMmMUjkxqcIpG6Crzd5lVyzAaGhap2q5dNVCubW0qpK_laZ6l292JQVJKQmPGaDz7QJnPzrwrVwEo1DXwYTtvKQJE5gnQpCAnv1B57ZzTbAnKedUMJHleaAuNpR21nsH5e4YguVXEnKCH8ffSUwDfLKBndc77iepoJ_-p8ulKdkn8JaNOg</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2442838799</pqid></control><display><type>article</type><title>Discovery of an all-donor aromatic [2]catenane</title><source>DOAJ Directory of Open Access Journals</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>PubMed Central Open Access</source><source>PubMed Central</source><creator>Gianga, Tiberiu-M ; Audibert, Edwige ; Trandafir, Anamaria ; Kociok-Köhn, Gabriele ; Panto, G. Dan</creator><creatorcontrib>Gianga, Tiberiu-M ; Audibert, Edwige ; Trandafir, Anamaria ; Kociok-Köhn, Gabriele ; Panto, G. Dan</creatorcontrib><description>We report herein the first all-donor aromatic [2]catenane formed through dynamic combinatorial chemistry, using single component libraries. The building block is a benzo[1,2-
b
:4,5-
b
′]dithiophene derivative, a π-donor molecule, with cysteine appendages that allow for disulfide exchange. The hydrophobic effect plays an essential role in the formation of the all-donor [2]catenane. The design of the building block allows the formation of a quasi-fused pentacyclic core, which enhances the stacking interactions between the cores. The [2]catenane has chiro-optical and fluorescent properties, being also the first known DCC-disulphide-based interlocked molecule to be fluorescent.
An all-donor [2]catenane has been synthesised
via
dynamic combinatorial chemistry. It features stacked benzodithiophenes which are quasi-pentacyclic through hydrogen bonding.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/d0sc04317f</identifier><identifier>PMID: 34094233</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Appendages ; Chemistry ; Combinatorial analysis ; Combinatorial chemistry ; Crystallography ; Fluorescence ; Optical properties</subject><ispartof>Chemical science (Cambridge), 2020-09, Vol.11 (35), p.9685-969</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><rights>This journal is © The Royal Society of Chemistry 2020 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c431t-2c5106b2e3394e8b1550e4c843e14dbe6e405d3cc4dee66424a817daa91d6a063</citedby><cites>FETCH-LOGICAL-c431t-2c5106b2e3394e8b1550e4c843e14dbe6e405d3cc4dee66424a817daa91d6a063</cites><orcidid>0000-0003-2200-550X ; 0000-0002-7186-1399 ; 0000-0002-6081-874X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162110/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162110/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27903,27904,53770,53772</link.rule.ids></links><search><creatorcontrib>Gianga, Tiberiu-M</creatorcontrib><creatorcontrib>Audibert, Edwige</creatorcontrib><creatorcontrib>Trandafir, Anamaria</creatorcontrib><creatorcontrib>Kociok-Köhn, Gabriele</creatorcontrib><creatorcontrib>Panto, G. Dan</creatorcontrib><title>Discovery of an all-donor aromatic [2]catenane</title><title>Chemical science (Cambridge)</title><description>We report herein the first all-donor aromatic [2]catenane formed through dynamic combinatorial chemistry, using single component libraries. The building block is a benzo[1,2-
b
:4,5-
b
′]dithiophene derivative, a π-donor molecule, with cysteine appendages that allow for disulfide exchange. The hydrophobic effect plays an essential role in the formation of the all-donor [2]catenane. The design of the building block allows the formation of a quasi-fused pentacyclic core, which enhances the stacking interactions between the cores. The [2]catenane has chiro-optical and fluorescent properties, being also the first known DCC-disulphide-based interlocked molecule to be fluorescent.
An all-donor [2]catenane has been synthesised
via
dynamic combinatorial chemistry. It features stacked benzodithiophenes which are quasi-pentacyclic through hydrogen bonding.</description><subject>Appendages</subject><subject>Chemistry</subject><subject>Combinatorial analysis</subject><subject>Combinatorial chemistry</subject><subject>Crystallography</subject><subject>Fluorescence</subject><subject>Optical properties</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kc1Lw0AQxRdRbKm9eBciXkRI3a8km4sgrVWh4EE9iSyb3YmmpNm6mxT637vaUtGDc5mB92OYNw-hY4JHBLP80mCvMWckK_dQn2JO4jRh-f5upriHht7PcSjGSEKzQ9RjHOecMtZHo0nltV2BW0e2jFQTqbqOjW2si5SzC9VWOnqhr1q10KgGjtBBqWoPw20foOfpzdP4Lp493N6Pr2exDqe0MdUJwWlBgbGcgyhIkmDgWnAGhJsCUuA4MUxrbgDSlFOuBMmMUjkxqcIpG6Crzd5lVyzAaGhap2q5dNVCubW0qpK_laZ6l292JQVJKQmPGaDz7QJnPzrwrVwEo1DXwYTtvKQJE5gnQpCAnv1B57ZzTbAnKedUMJHleaAuNpR21nsH5e4YguVXEnKCH8ffSUwDfLKBndc77iepoJ_-p8ulKdkn8JaNOg</recordid><startdate>20200921</startdate><enddate>20200921</enddate><creator>Gianga, Tiberiu-M</creator><creator>Audibert, Edwige</creator><creator>Trandafir, Anamaria</creator><creator>Kociok-Köhn, Gabriele</creator><creator>Panto, G. Dan</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-2200-550X</orcidid><orcidid>https://orcid.org/0000-0002-7186-1399</orcidid><orcidid>https://orcid.org/0000-0002-6081-874X</orcidid></search><sort><creationdate>20200921</creationdate><title>Discovery of an all-donor aromatic [2]catenane</title><author>Gianga, Tiberiu-M ; Audibert, Edwige ; Trandafir, Anamaria ; Kociok-Köhn, Gabriele ; Panto, G. Dan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c431t-2c5106b2e3394e8b1550e4c843e14dbe6e405d3cc4dee66424a817daa91d6a063</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Appendages</topic><topic>Chemistry</topic><topic>Combinatorial analysis</topic><topic>Combinatorial chemistry</topic><topic>Crystallography</topic><topic>Fluorescence</topic><topic>Optical properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gianga, Tiberiu-M</creatorcontrib><creatorcontrib>Audibert, Edwige</creatorcontrib><creatorcontrib>Trandafir, Anamaria</creatorcontrib><creatorcontrib>Kociok-Köhn, Gabriele</creatorcontrib><creatorcontrib>Panto, G. Dan</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gianga, Tiberiu-M</au><au>Audibert, Edwige</au><au>Trandafir, Anamaria</au><au>Kociok-Köhn, Gabriele</au><au>Panto, G. Dan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Discovery of an all-donor aromatic [2]catenane</atitle><jtitle>Chemical science (Cambridge)</jtitle><date>2020-09-21</date><risdate>2020</risdate><volume>11</volume><issue>35</issue><spage>9685</spage><epage>969</epage><pages>9685-969</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>We report herein the first all-donor aromatic [2]catenane formed through dynamic combinatorial chemistry, using single component libraries. The building block is a benzo[1,2-
b
:4,5-
b
′]dithiophene derivative, a π-donor molecule, with cysteine appendages that allow for disulfide exchange. The hydrophobic effect plays an essential role in the formation of the all-donor [2]catenane. The design of the building block allows the formation of a quasi-fused pentacyclic core, which enhances the stacking interactions between the cores. The [2]catenane has chiro-optical and fluorescent properties, being also the first known DCC-disulphide-based interlocked molecule to be fluorescent.
An all-donor [2]catenane has been synthesised
via
dynamic combinatorial chemistry. It features stacked benzodithiophenes which are quasi-pentacyclic through hydrogen bonding.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><pmid>34094233</pmid><doi>10.1039/d0sc04317f</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-2200-550X</orcidid><orcidid>https://orcid.org/0000-0002-7186-1399</orcidid><orcidid>https://orcid.org/0000-0002-6081-874X</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2041-6520 |
| ispartof | Chemical science (Cambridge), 2020-09, Vol.11 (35), p.9685-969 |
| issn | 2041-6520 2041-6539 |
| language | eng |
| recordid | cdi_rsc_primary_d0sc04317f |
| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central Open Access; PubMed Central |
| subjects | Appendages Chemistry Combinatorial analysis Combinatorial chemistry Crystallography Fluorescence Optical properties |
| title | Discovery of an all-donor aromatic [2]catenane |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-23T10%3A41%3A34IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_rsc_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Discovery%20of%20an%20all-donor%20aromatic%20%5B2%5Dcatenane&rft.jtitle=Chemical%20science%20(Cambridge)&rft.au=Gianga,%20Tiberiu-M&rft.date=2020-09-21&rft.volume=11&rft.issue=35&rft.spage=9685&rft.epage=969&rft.pages=9685-969&rft.issn=2041-6520&rft.eissn=2041-6539&rft_id=info:doi/10.1039/d0sc04317f&rft_dat=%3Cproquest_rsc_p%3E2442838799%3C/proquest_rsc_p%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2442838799&rft_id=info:pmid/34094233&rfr_iscdi=true |