Solvent Effects on the Actinic Step of Donor–Acceptor Stenhouse Adduct Photoswitching
Donor–acceptor Stenhouse adducts (DASAs) are negative photochromes that switch with visible light and are highly promising for applications ranging from smart materials to biological systems. However, the strong solvent dependence of the photoswitching kinetics limits their application. The nature o...
Gespeichert in:
| Veröffentlicht in: | Angewandte Chemie International Edition 2018-07, Vol.57 (27), p.8063-8068 |
|---|---|
| Hauptverfasser: | , , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 8068 |
|---|---|
| container_issue | 27 |
| container_start_page | 8063 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 57 |
| creator | Lerch, Michael M. Di Donato, Mariangela Laurent, Adèle D. Medved', Miroslav Iagatti, Alessandro Bussotti, Laura Lapini, Andrea Buma, Wybren Jan Foggi, Paolo Szymański, Wiktor Feringa, Ben L. |
| description | Donor–acceptor Stenhouse adducts (DASAs) are negative photochromes that switch with visible light and are highly promising for applications ranging from smart materials to biological systems. However, the strong solvent dependence of the photoswitching kinetics limits their application. The nature of the photoswitching mechanism in different solvents is key for addressing the solvatochromism of DASAs, but as yet has remained elusive. Here, we employ spectroscopic analyses and TD‐DFT calculations to reveal changing solvatochromic shifts and energies of the species involved in DASA photoswitching. Time‐resolved visible pump‐probe spectroscopy suggests that the primary photochemical step remains the same, irrespective of the polarity and protic nature of the solvent. Disentangling the different factors determining the solvent‐dependence of DASA photoswitching, presented here, is crucial for the rational development of applications in a wide range of different media.
DASAs (dis)solved: The actinic step of the photoswitching mechanism of donor–acceptor Stenhouse adducts is similar across a range of solvents from apolar aprotic to polar protic. The energies and absorption spectra of photoswitching intermediates, however, change with solvent polarity and the protic nature of the solvent, affecting the overall photoswitching behavior. |
| doi_str_mv | 10.1002/anie.201803058 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_6055754</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2047251592</sourcerecordid><originalsourceid>FETCH-LOGICAL-c5398-97ba52b2c2200cbbb835df0dabdabcb6b469b7bb4c17ccaf75c380cff7b377f63</originalsourceid><addsrcrecordid>eNqFkc1u1DAUhSMEoqWwZYkisYFFBv_EcbxBispAK40AqSCWVnxjN64y9tR2puqOd-ANeRI8mjJAN0iWbPl-99jnnqJ4jtECI0Te9M7qBUG4RRSx9kFxjBnBFeWcPsznmtKKtwwfFU9ivMp826LmcXFERFuzRojj4tuFn7bapXJpjIYUS-_KNOqyg2SdhfIi6U3pTfnOOx9-fv_RAehN8mFXcKOfY0aHYYZUfh598vHGJhitu3xaPDL9FPWzu_2k-Pp--eX0rFp9-nB-2q0qYFS0leCqZ0QRIAQhUEq1lA0GDb3KC1Sj6kYorlQNmAP0hjOgLQJjuMoeTUNPird73c2s1nqAbCX0k9wEu-7DrfS9lf9WnB3lpd_KBjHGWZ0FXu8FxnttZ91K7u4QFgg1gm9xZl_dPRb89axjkmsbQU9T73QehSSo5oRhJkhGX95Dr_wcXB5FppjAFAksMrXYUxB8jEGbww8wkrt85S5fecg3N7z42-4B_x1oBsQeuLGTvv2PnOw-ni__iP8CmbG0HQ</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2059130919</pqid></control><display><type>article</type><title>Solvent Effects on the Actinic Step of Donor–Acceptor Stenhouse Adduct Photoswitching</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Lerch, Michael M. ; Di Donato, Mariangela ; Laurent, Adèle D. ; Medved', Miroslav ; Iagatti, Alessandro ; Bussotti, Laura ; Lapini, Andrea ; Buma, Wybren Jan ; Foggi, Paolo ; Szymański, Wiktor ; Feringa, Ben L.</creator><creatorcontrib>Lerch, Michael M. ; Di Donato, Mariangela ; Laurent, Adèle D. ; Medved', Miroslav ; Iagatti, Alessandro ; Bussotti, Laura ; Lapini, Andrea ; Buma, Wybren Jan ; Foggi, Paolo ; Szymański, Wiktor ; Feringa, Ben L.</creatorcontrib><description>Donor–acceptor Stenhouse adducts (DASAs) are negative photochromes that switch with visible light and are highly promising for applications ranging from smart materials to biological systems. However, the strong solvent dependence of the photoswitching kinetics limits their application. The nature of the photoswitching mechanism in different solvents is key for addressing the solvatochromism of DASAs, but as yet has remained elusive. Here, we employ spectroscopic analyses and TD‐DFT calculations to reveal changing solvatochromic shifts and energies of the species involved in DASA photoswitching. Time‐resolved visible pump‐probe spectroscopy suggests that the primary photochemical step remains the same, irrespective of the polarity and protic nature of the solvent. Disentangling the different factors determining the solvent‐dependence of DASA photoswitching, presented here, is crucial for the rational development of applications in a wide range of different media.
DASAs (dis)solved: The actinic step of the photoswitching mechanism of donor–acceptor Stenhouse adducts is similar across a range of solvents from apolar aprotic to polar protic. The energies and absorption spectra of photoswitching intermediates, however, change with solvent polarity and the protic nature of the solvent, affecting the overall photoswitching behavior.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201803058</identifier><identifier>PMID: 29845699</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Adducts ; Biological materials ; Chemical Sciences ; Communication ; Communications ; Dependence ; donor–acceptor Stenhouse adducts ; Kinetics ; or physical chemistry ; Photochemicals ; Photochromes ; photoswitches ; Polarity ; Smart materials ; Solvent effect ; solvent effects ; Solvents ; Spectroscopy ; Theoretical and ; visible light</subject><ispartof>Angewandte Chemie International Edition, 2018-07, Vol.57 (27), p.8063-8068</ispartof><rights>2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</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-c5398-97ba52b2c2200cbbb835df0dabdabcb6b469b7bb4c17ccaf75c380cff7b377f63</citedby><cites>FETCH-LOGICAL-c5398-97ba52b2c2200cbbb835df0dabdabcb6b469b7bb4c17ccaf75c380cff7b377f63</cites><orcidid>0000-0001-9553-9014 ; 0000-0003-0588-8435 ; 0000-0003-3600-0849 ; 0000-0002-9754-9248 ; 0000-0001-8599-1031 ; 0000-0002-1265-8016 ; 0000-0002-2204-7673 ; 0000-0002-2985-6721 ; 0000-0003-1765-0301 ; 0000-0002-6596-7031</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%2Fanie.201803058$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201803058$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,776,780,881,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29845699$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-01900697$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Lerch, Michael M.</creatorcontrib><creatorcontrib>Di Donato, Mariangela</creatorcontrib><creatorcontrib>Laurent, Adèle D.</creatorcontrib><creatorcontrib>Medved', Miroslav</creatorcontrib><creatorcontrib>Iagatti, Alessandro</creatorcontrib><creatorcontrib>Bussotti, Laura</creatorcontrib><creatorcontrib>Lapini, Andrea</creatorcontrib><creatorcontrib>Buma, Wybren Jan</creatorcontrib><creatorcontrib>Foggi, Paolo</creatorcontrib><creatorcontrib>Szymański, Wiktor</creatorcontrib><creatorcontrib>Feringa, Ben L.</creatorcontrib><title>Solvent Effects on the Actinic Step of Donor–Acceptor Stenhouse Adduct Photoswitching</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Donor–acceptor Stenhouse adducts (DASAs) are negative photochromes that switch with visible light and are highly promising for applications ranging from smart materials to biological systems. However, the strong solvent dependence of the photoswitching kinetics limits their application. The nature of the photoswitching mechanism in different solvents is key for addressing the solvatochromism of DASAs, but as yet has remained elusive. Here, we employ spectroscopic analyses and TD‐DFT calculations to reveal changing solvatochromic shifts and energies of the species involved in DASA photoswitching. Time‐resolved visible pump‐probe spectroscopy suggests that the primary photochemical step remains the same, irrespective of the polarity and protic nature of the solvent. Disentangling the different factors determining the solvent‐dependence of DASA photoswitching, presented here, is crucial for the rational development of applications in a wide range of different media.
DASAs (dis)solved: The actinic step of the photoswitching mechanism of donor–acceptor Stenhouse adducts is similar across a range of solvents from apolar aprotic to polar protic. The energies and absorption spectra of photoswitching intermediates, however, change with solvent polarity and the protic nature of the solvent, affecting the overall photoswitching behavior.</description><subject>Adducts</subject><subject>Biological materials</subject><subject>Chemical Sciences</subject><subject>Communication</subject><subject>Communications</subject><subject>Dependence</subject><subject>donor–acceptor Stenhouse adducts</subject><subject>Kinetics</subject><subject>or physical chemistry</subject><subject>Photochemicals</subject><subject>Photochromes</subject><subject>photoswitches</subject><subject>Polarity</subject><subject>Smart materials</subject><subject>Solvent effect</subject><subject>solvent effects</subject><subject>Solvents</subject><subject>Spectroscopy</subject><subject>Theoretical and</subject><subject>visible light</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><recordid>eNqFkc1u1DAUhSMEoqWwZYkisYFFBv_EcbxBispAK40AqSCWVnxjN64y9tR2puqOd-ANeRI8mjJAN0iWbPl-99jnnqJ4jtECI0Te9M7qBUG4RRSx9kFxjBnBFeWcPsznmtKKtwwfFU9ivMp826LmcXFERFuzRojj4tuFn7bapXJpjIYUS-_KNOqyg2SdhfIi6U3pTfnOOx9-fv_RAehN8mFXcKOfY0aHYYZUfh598vHGJhitu3xaPDL9FPWzu_2k-Pp--eX0rFp9-nB-2q0qYFS0leCqZ0QRIAQhUEq1lA0GDb3KC1Sj6kYorlQNmAP0hjOgLQJjuMoeTUNPird73c2s1nqAbCX0k9wEu-7DrfS9lf9WnB3lpd_KBjHGWZ0FXu8FxnttZ91K7u4QFgg1gm9xZl_dPRb89axjkmsbQU9T73QehSSo5oRhJkhGX95Dr_wcXB5FppjAFAksMrXYUxB8jEGbww8wkrt85S5fecg3N7z42-4B_x1oBsQeuLGTvv2PnOw-ni__iP8CmbG0HQ</recordid><startdate>20180702</startdate><enddate>20180702</enddate><creator>Lerch, Michael M.</creator><creator>Di Donato, Mariangela</creator><creator>Laurent, Adèle D.</creator><creator>Medved', Miroslav</creator><creator>Iagatti, Alessandro</creator><creator>Bussotti, Laura</creator><creator>Lapini, Andrea</creator><creator>Buma, Wybren Jan</creator><creator>Foggi, Paolo</creator><creator>Szymański, Wiktor</creator><creator>Feringa, Ben L.</creator><general>Wiley Subscription Services, Inc</general><general>Wiley-VCH Verlag</general><general>John Wiley and Sons Inc</general><scope>24P</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>1XC</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-9553-9014</orcidid><orcidid>https://orcid.org/0000-0003-0588-8435</orcidid><orcidid>https://orcid.org/0000-0003-3600-0849</orcidid><orcidid>https://orcid.org/0000-0002-9754-9248</orcidid><orcidid>https://orcid.org/0000-0001-8599-1031</orcidid><orcidid>https://orcid.org/0000-0002-1265-8016</orcidid><orcidid>https://orcid.org/0000-0002-2204-7673</orcidid><orcidid>https://orcid.org/0000-0002-2985-6721</orcidid><orcidid>https://orcid.org/0000-0003-1765-0301</orcidid><orcidid>https://orcid.org/0000-0002-6596-7031</orcidid></search><sort><creationdate>20180702</creationdate><title>Solvent Effects on the Actinic Step of Donor–Acceptor Stenhouse Adduct Photoswitching</title><author>Lerch, Michael M. ; Di Donato, Mariangela ; Laurent, Adèle D. ; Medved', Miroslav ; Iagatti, Alessandro ; Bussotti, Laura ; Lapini, Andrea ; Buma, Wybren Jan ; Foggi, Paolo ; Szymański, Wiktor ; Feringa, Ben L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5398-97ba52b2c2200cbbb835df0dabdabcb6b469b7bb4c17ccaf75c380cff7b377f63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Adducts</topic><topic>Biological materials</topic><topic>Chemical Sciences</topic><topic>Communication</topic><topic>Communications</topic><topic>Dependence</topic><topic>donor–acceptor Stenhouse adducts</topic><topic>Kinetics</topic><topic>or physical chemistry</topic><topic>Photochemicals</topic><topic>Photochromes</topic><topic>photoswitches</topic><topic>Polarity</topic><topic>Smart materials</topic><topic>Solvent effect</topic><topic>solvent effects</topic><topic>Solvents</topic><topic>Spectroscopy</topic><topic>Theoretical and</topic><topic>visible light</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lerch, Michael M.</creatorcontrib><creatorcontrib>Di Donato, Mariangela</creatorcontrib><creatorcontrib>Laurent, Adèle D.</creatorcontrib><creatorcontrib>Medved', Miroslav</creatorcontrib><creatorcontrib>Iagatti, Alessandro</creatorcontrib><creatorcontrib>Bussotti, Laura</creatorcontrib><creatorcontrib>Lapini, Andrea</creatorcontrib><creatorcontrib>Buma, Wybren Jan</creatorcontrib><creatorcontrib>Foggi, Paolo</creatorcontrib><creatorcontrib>Szymański, Wiktor</creatorcontrib><creatorcontrib>Feringa, Ben L.</creatorcontrib><collection>Wiley Online Library Open Access</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lerch, Michael M.</au><au>Di Donato, Mariangela</au><au>Laurent, Adèle D.</au><au>Medved', Miroslav</au><au>Iagatti, Alessandro</au><au>Bussotti, Laura</au><au>Lapini, Andrea</au><au>Buma, Wybren Jan</au><au>Foggi, Paolo</au><au>Szymański, Wiktor</au><au>Feringa, Ben L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Solvent Effects on the Actinic Step of Donor–Acceptor Stenhouse Adduct Photoswitching</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2018-07-02</date><risdate>2018</risdate><volume>57</volume><issue>27</issue><spage>8063</spage><epage>8068</epage><pages>8063-8068</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Donor–acceptor Stenhouse adducts (DASAs) are negative photochromes that switch with visible light and are highly promising for applications ranging from smart materials to biological systems. However, the strong solvent dependence of the photoswitching kinetics limits their application. The nature of the photoswitching mechanism in different solvents is key for addressing the solvatochromism of DASAs, but as yet has remained elusive. Here, we employ spectroscopic analyses and TD‐DFT calculations to reveal changing solvatochromic shifts and energies of the species involved in DASA photoswitching. Time‐resolved visible pump‐probe spectroscopy suggests that the primary photochemical step remains the same, irrespective of the polarity and protic nature of the solvent. Disentangling the different factors determining the solvent‐dependence of DASA photoswitching, presented here, is crucial for the rational development of applications in a wide range of different media.
DASAs (dis)solved: The actinic step of the photoswitching mechanism of donor–acceptor Stenhouse adducts is similar across a range of solvents from apolar aprotic to polar protic. The energies and absorption spectra of photoswitching intermediates, however, change with solvent polarity and the protic nature of the solvent, affecting the overall photoswitching behavior.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>29845699</pmid><doi>10.1002/anie.201803058</doi><tpages>6</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0001-9553-9014</orcidid><orcidid>https://orcid.org/0000-0003-0588-8435</orcidid><orcidid>https://orcid.org/0000-0003-3600-0849</orcidid><orcidid>https://orcid.org/0000-0002-9754-9248</orcidid><orcidid>https://orcid.org/0000-0001-8599-1031</orcidid><orcidid>https://orcid.org/0000-0002-1265-8016</orcidid><orcidid>https://orcid.org/0000-0002-2204-7673</orcidid><orcidid>https://orcid.org/0000-0002-2985-6721</orcidid><orcidid>https://orcid.org/0000-0003-1765-0301</orcidid><orcidid>https://orcid.org/0000-0002-6596-7031</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2018-07, Vol.57 (27), p.8063-8068 |
| issn | 1433-7851 1521-3773 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_6055754 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Adducts Biological materials Chemical Sciences Communication Communications Dependence donor–acceptor Stenhouse adducts Kinetics or physical chemistry Photochemicals Photochromes photoswitches Polarity Smart materials Solvent effect solvent effects Solvents Spectroscopy Theoretical and visible light |
| title | Solvent Effects on the Actinic Step of Donor–Acceptor Stenhouse Adduct Photoswitching |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-03T00%3A08%3A36IST&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=Solvent%20Effects%20on%20the%20Actinic%20Step%20of%20Donor%E2%80%93Acceptor%20Stenhouse%20Adduct%20Photoswitching&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Lerch,%20Michael%20M.&rft.date=2018-07-02&rft.volume=57&rft.issue=27&rft.spage=8063&rft.epage=8068&rft.pages=8063-8068&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.201803058&rft_dat=%3Cproquest_pubme%3E2047251592%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=2059130919&rft_id=info:pmid/29845699&rfr_iscdi=true |