Organosulfur Materials with High Photo- and Photo-Oxidation Stability: 10-Anthryl Sulfoxides and Sulfones and Their Photophysical Properties Dependent on the Sulfur Oxidation State
While few studies show only symmetrical and poorly mono-SO (n = 0-2) substituted acenes, in this study, we present a synthesis of a new group of unsymmetrical, significantly substituted derivatives, which revealed unique photophysical properties. Both sulfides (S), sulfoxides (SO) and sulfones (SO )...
Gespeichert in:
| Veröffentlicht in: | Materials 2021-06, Vol.14 (13), p.3506 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | |
|---|---|
| container_issue | 13 |
| container_start_page | 3506 |
| container_title | Materials |
| container_volume | 14 |
| creator | Bałczewski, Piotr Kowalska, Emilia Różycka-Sokołowska, Ewa Uznański, Paweł Wilk, Joanna Koprowski, Marek Owsianik, Krzysztof Marciniak, Bernard |
| description | While few studies show only symmetrical and poorly mono-SO
(n = 0-2) substituted acenes, in this study, we present a synthesis of a new group of unsymmetrical, significantly substituted derivatives, which revealed unique photophysical properties. Both sulfides (S), sulfoxides (SO) and sulfones (SO
) showed very high photochemical stabilities, unusual for these groups, during UV-irradiation at 254/365 nm (air O
and Ar), which was higher than any found in the literature. For the (S)/(SO) series (254 nm), the stabilities of 80-519 min. (air O
and Ar) were found. At 365 nm, stabilities of 124-812 min./(air O
) for (S)/(SO) and higher for (SO
) were observed. Photoluminescence lifetimes of (SO
) of the lower anthryl symmetry remained in the following order: (SO
) < (S) < (SO); those with full symmetry were in the following order: (S) < (SO) < (SO
). The enhanced photostability was explained with DFT/MS/Hammett's constants, which showed the leading role of the SO
groups in stabilization of HOMO/LUMO frontier orbitals. The SO
(n = 0-2) substituted acenes turned out to be tunable violet/blue/green emitters by oxidation of S atoms and the introduction of rich substitution. |
| doi_str_mv | 10.3390/ma14133506 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_8269563</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2549481524</sourcerecordid><originalsourceid>FETCH-LOGICAL-c406t-1517c3cafc84b31ecec277f7fdf6689b6645a10c283f0dee89a94196db230243</originalsourceid><addsrcrecordid>eNpdkttu3CAQhlHVqonS3PQBKqTeVJXcgMHY9KJSlB4SKdVGyt4jjMdrIi-4gNPue_UBS3a3OXEzM5pvfn7EIPSWkk-MSXKy1pRTxioiXqBDKqUoqOT85aP8AB3HeEPyYYw2pXyNDhgvCa05OUR_F2GlnY_z2M8B_9QJgtVjxL9tGvC5XQ34avDJF1i7bp8u_thOJ-sdvk66taNNm8-YkuLUpSFsRnydtXxmIG6HtqXbF8sBbNjpTMMmWqNHfBX8BCHZjHyFCVwHLuGsngbYDmdfT65M8Aa96rNJON7HI7T8_m15dl5cLn5cnJ1eFoYTkQpa0dowo3vT8JZRMGDKuu7rvuuFaGQrBK80JaZsWE86gEZqyakUXVsyUnJ2hL7sZKe5XUNnsq-gRzUFu9Zho7y26mnH2UGt_K1qSiErwbLAh71A8L9miEmtbTQwjtqBn6MqK95wUtWyzuj7Z-iNn4PLr7ujJG9otXX0cUeZ4GMM0N-boUTdrYN6WIcMv3ts_x79__nsH94us6Y</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2549481524</pqid></control><display><type>article</type><title>Organosulfur Materials with High Photo- and Photo-Oxidation Stability: 10-Anthryl Sulfoxides and Sulfones and Their Photophysical Properties Dependent on the Sulfur Oxidation State</title><source>MDPI - Multidisciplinary Digital Publishing Institute</source><source>Free E-Journal (出版社公開部分のみ）</source><source>PubMed Central</source><source>Free Full-Text Journals in Chemistry</source><source>PubMed Central Open Access</source><creator>Bałczewski, Piotr ; Kowalska, Emilia ; Różycka-Sokołowska, Ewa ; Uznański, Paweł ; Wilk, Joanna ; Koprowski, Marek ; Owsianik, Krzysztof ; Marciniak, Bernard</creator><creatorcontrib>Bałczewski, Piotr ; Kowalska, Emilia ; Różycka-Sokołowska, Ewa ; Uznański, Paweł ; Wilk, Joanna ; Koprowski, Marek ; Owsianik, Krzysztof ; Marciniak, Bernard</creatorcontrib><description>While few studies show only symmetrical and poorly mono-SO
(n = 0-2) substituted acenes, in this study, we present a synthesis of a new group of unsymmetrical, significantly substituted derivatives, which revealed unique photophysical properties. Both sulfides (S), sulfoxides (SO) and sulfones (SO
) showed very high photochemical stabilities, unusual for these groups, during UV-irradiation at 254/365 nm (air O
and Ar), which was higher than any found in the literature. For the (S)/(SO) series (254 nm), the stabilities of 80-519 min. (air O
and Ar) were found. At 365 nm, stabilities of 124-812 min./(air O
) for (S)/(SO) and higher for (SO
) were observed. Photoluminescence lifetimes of (SO
) of the lower anthryl symmetry remained in the following order: (SO
) < (S) < (SO); those with full symmetry were in the following order: (S) < (SO) < (SO
). The enhanced photostability was explained with DFT/MS/Hammett's constants, which showed the leading role of the SO
groups in stabilization of HOMO/LUMO frontier orbitals. The SO
(n = 0-2) substituted acenes turned out to be tunable violet/blue/green emitters by oxidation of S atoms and the introduction of rich substitution.</description><identifier>ISSN: 1996-1944</identifier><identifier>EISSN: 1996-1944</identifier><identifier>DOI: 10.3390/ma14133506</identifier><identifier>PMID: 34201740</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Chromatography ; Emitters ; Investigations ; Light emitting diodes ; Molecular orbitals ; Oxidation ; Photodegradation ; Photoluminescence ; Substitutes ; Sulfones ; Sulfoxides ; Symmetry ; Ultraviolet radiation ; Valence</subject><ispartof>Materials, 2021-06, Vol.14 (13), p.3506</ispartof><rights>2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2021 by the authors. 2021</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c406t-1517c3cafc84b31ecec277f7fdf6689b6645a10c283f0dee89a94196db230243</citedby><cites>FETCH-LOGICAL-c406t-1517c3cafc84b31ecec277f7fdf6689b6645a10c283f0dee89a94196db230243</cites><orcidid>0000-0001-5981-551X ; 0000-0002-9053-3315 ; 0000-0003-0122-1326 ; 0000-0001-5980-6939 ; 0000-0002-4604-4901</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/PMC8269563/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8269563/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34201740$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bałczewski, Piotr</creatorcontrib><creatorcontrib>Kowalska, Emilia</creatorcontrib><creatorcontrib>Różycka-Sokołowska, Ewa</creatorcontrib><creatorcontrib>Uznański, Paweł</creatorcontrib><creatorcontrib>Wilk, Joanna</creatorcontrib><creatorcontrib>Koprowski, Marek</creatorcontrib><creatorcontrib>Owsianik, Krzysztof</creatorcontrib><creatorcontrib>Marciniak, Bernard</creatorcontrib><title>Organosulfur Materials with High Photo- and Photo-Oxidation Stability: 10-Anthryl Sulfoxides and Sulfones and Their Photophysical Properties Dependent on the Sulfur Oxidation State</title><title>Materials</title><addtitle>Materials (Basel)</addtitle><description>While few studies show only symmetrical and poorly mono-SO
(n = 0-2) substituted acenes, in this study, we present a synthesis of a new group of unsymmetrical, significantly substituted derivatives, which revealed unique photophysical properties. Both sulfides (S), sulfoxides (SO) and sulfones (SO
) showed very high photochemical stabilities, unusual for these groups, during UV-irradiation at 254/365 nm (air O
and Ar), which was higher than any found in the literature. For the (S)/(SO) series (254 nm), the stabilities of 80-519 min. (air O
and Ar) were found. At 365 nm, stabilities of 124-812 min./(air O
) for (S)/(SO) and higher for (SO
) were observed. Photoluminescence lifetimes of (SO
) of the lower anthryl symmetry remained in the following order: (SO
) < (S) < (SO); those with full symmetry were in the following order: (S) < (SO) < (SO
). The enhanced photostability was explained with DFT/MS/Hammett's constants, which showed the leading role of the SO
groups in stabilization of HOMO/LUMO frontier orbitals. The SO
(n = 0-2) substituted acenes turned out to be tunable violet/blue/green emitters by oxidation of S atoms and the introduction of rich substitution.</description><subject>Chromatography</subject><subject>Emitters</subject><subject>Investigations</subject><subject>Light emitting diodes</subject><subject>Molecular orbitals</subject><subject>Oxidation</subject><subject>Photodegradation</subject><subject>Photoluminescence</subject><subject>Substitutes</subject><subject>Sulfones</subject><subject>Sulfoxides</subject><subject>Symmetry</subject><subject>Ultraviolet radiation</subject><subject>Valence</subject><issn>1996-1944</issn><issn>1996-1944</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>BENPR</sourceid><recordid>eNpdkttu3CAQhlHVqonS3PQBKqTeVJXcgMHY9KJSlB4SKdVGyt4jjMdrIi-4gNPue_UBS3a3OXEzM5pvfn7EIPSWkk-MSXKy1pRTxioiXqBDKqUoqOT85aP8AB3HeEPyYYw2pXyNDhgvCa05OUR_F2GlnY_z2M8B_9QJgtVjxL9tGvC5XQ34avDJF1i7bp8u_thOJ-sdvk66taNNm8-YkuLUpSFsRnydtXxmIG6HtqXbF8sBbNjpTMMmWqNHfBX8BCHZjHyFCVwHLuGsngbYDmdfT65M8Aa96rNJON7HI7T8_m15dl5cLn5cnJ1eFoYTkQpa0dowo3vT8JZRMGDKuu7rvuuFaGQrBK80JaZsWE86gEZqyakUXVsyUnJ2hL7sZKe5XUNnsq-gRzUFu9Zho7y26mnH2UGt_K1qSiErwbLAh71A8L9miEmtbTQwjtqBn6MqK95wUtWyzuj7Z-iNn4PLr7ujJG9otXX0cUeZ4GMM0N-boUTdrYN6WIcMv3ts_x79__nsH94us6Y</recordid><startdate>20210623</startdate><enddate>20210623</enddate><creator>Bałczewski, Piotr</creator><creator>Kowalska, Emilia</creator><creator>Różycka-Sokołowska, Ewa</creator><creator>Uznański, Paweł</creator><creator>Wilk, Joanna</creator><creator>Koprowski, Marek</creator><creator>Owsianik, Krzysztof</creator><creator>Marciniak, Bernard</creator><general>MDPI AG</general><general>MDPI</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-5981-551X</orcidid><orcidid>https://orcid.org/0000-0002-9053-3315</orcidid><orcidid>https://orcid.org/0000-0003-0122-1326</orcidid><orcidid>https://orcid.org/0000-0001-5980-6939</orcidid><orcidid>https://orcid.org/0000-0002-4604-4901</orcidid></search><sort><creationdate>20210623</creationdate><title>Organosulfur Materials with High Photo- and Photo-Oxidation Stability: 10-Anthryl Sulfoxides and Sulfones and Their Photophysical Properties Dependent on the Sulfur Oxidation State</title><author>Bałczewski, Piotr ; Kowalska, Emilia ; Różycka-Sokołowska, Ewa ; Uznański, Paweł ; Wilk, Joanna ; Koprowski, Marek ; Owsianik, Krzysztof ; Marciniak, Bernard</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c406t-1517c3cafc84b31ecec277f7fdf6689b6645a10c283f0dee89a94196db230243</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Chromatography</topic><topic>Emitters</topic><topic>Investigations</topic><topic>Light emitting diodes</topic><topic>Molecular orbitals</topic><topic>Oxidation</topic><topic>Photodegradation</topic><topic>Photoluminescence</topic><topic>Substitutes</topic><topic>Sulfones</topic><topic>Sulfoxides</topic><topic>Symmetry</topic><topic>Ultraviolet radiation</topic><topic>Valence</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bałczewski, Piotr</creatorcontrib><creatorcontrib>Kowalska, Emilia</creatorcontrib><creatorcontrib>Różycka-Sokołowska, Ewa</creatorcontrib><creatorcontrib>Uznański, Paweł</creatorcontrib><creatorcontrib>Wilk, Joanna</creatorcontrib><creatorcontrib>Koprowski, Marek</creatorcontrib><creatorcontrib>Owsianik, Krzysztof</creatorcontrib><creatorcontrib>Marciniak, Bernard</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>https://resources.nclive.org/materials</collection><collection>Materials Science Collection</collection><collection>Publicly Available Content (ProQuest)</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Materials</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bałczewski, Piotr</au><au>Kowalska, Emilia</au><au>Różycka-Sokołowska, Ewa</au><au>Uznański, Paweł</au><au>Wilk, Joanna</au><au>Koprowski, Marek</au><au>Owsianik, Krzysztof</au><au>Marciniak, Bernard</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Organosulfur Materials with High Photo- and Photo-Oxidation Stability: 10-Anthryl Sulfoxides and Sulfones and Their Photophysical Properties Dependent on the Sulfur Oxidation State</atitle><jtitle>Materials</jtitle><addtitle>Materials (Basel)</addtitle><date>2021-06-23</date><risdate>2021</risdate><volume>14</volume><issue>13</issue><spage>3506</spage><pages>3506-</pages><issn>1996-1944</issn><eissn>1996-1944</eissn><abstract>While few studies show only symmetrical and poorly mono-SO
(n = 0-2) substituted acenes, in this study, we present a synthesis of a new group of unsymmetrical, significantly substituted derivatives, which revealed unique photophysical properties. Both sulfides (S), sulfoxides (SO) and sulfones (SO
) showed very high photochemical stabilities, unusual for these groups, during UV-irradiation at 254/365 nm (air O
and Ar), which was higher than any found in the literature. For the (S)/(SO) series (254 nm), the stabilities of 80-519 min. (air O
and Ar) were found. At 365 nm, stabilities of 124-812 min./(air O
) for (S)/(SO) and higher for (SO
) were observed. Photoluminescence lifetimes of (SO
) of the lower anthryl symmetry remained in the following order: (SO
) < (S) < (SO); those with full symmetry were in the following order: (S) < (SO) < (SO
). The enhanced photostability was explained with DFT/MS/Hammett's constants, which showed the leading role of the SO
groups in stabilization of HOMO/LUMO frontier orbitals. The SO
(n = 0-2) substituted acenes turned out to be tunable violet/blue/green emitters by oxidation of S atoms and the introduction of rich substitution.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>34201740</pmid><doi>10.3390/ma14133506</doi><orcidid>https://orcid.org/0000-0001-5981-551X</orcidid><orcidid>https://orcid.org/0000-0002-9053-3315</orcidid><orcidid>https://orcid.org/0000-0003-0122-1326</orcidid><orcidid>https://orcid.org/0000-0001-5980-6939</orcidid><orcidid>https://orcid.org/0000-0002-4604-4901</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1996-1944 |
| ispartof | Materials, 2021-06, Vol.14 (13), p.3506 |
| issn | 1996-1944 1996-1944 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_8269563 |
| source | MDPI - Multidisciplinary Digital Publishing Institute; Free E-Journal (出版社公開部分のみ）; PubMed Central; Free Full-Text Journals in Chemistry; PubMed Central Open Access |
| subjects | Chromatography Emitters Investigations Light emitting diodes Molecular orbitals Oxidation Photodegradation Photoluminescence Substitutes Sulfones Sulfoxides Symmetry Ultraviolet radiation Valence |
| title | Organosulfur Materials with High Photo- and Photo-Oxidation Stability: 10-Anthryl Sulfoxides and Sulfones and Their Photophysical Properties Dependent on the Sulfur Oxidation State |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-12T07%3A35%3A32IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Organosulfur%20Materials%20with%20High%20Photo-%20and%20Photo-Oxidation%20Stability:%2010-Anthryl%20Sulfoxides%20and%20Sulfones%20and%20Their%20Photophysical%20Properties%20Dependent%20on%20the%20Sulfur%20Oxidation%20State&rft.jtitle=Materials&rft.au=Ba%C5%82czewski,%20Piotr&rft.date=2021-06-23&rft.volume=14&rft.issue=13&rft.spage=3506&rft.pages=3506-&rft.issn=1996-1944&rft.eissn=1996-1944&rft_id=info:doi/10.3390/ma14133506&rft_dat=%3Cproquest_pubme%3E2549481524%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2549481524&rft_id=info:pmid/34201740&rfr_iscdi=true |