Synthesis and photophysical properties of extended π conjugated naphthalimides

Synthesis and photophysical properties of extended π conjugated naphthalimides

A series of π conjugated naphthalimide derivatives having an imide group as an acceptor conjugated with a methoxy arylethynyl or a methoxyphenyl triazole as a donor were prepared by Sonogashira coupling or “click” chemistry. Their photophysical properties were investigated by steady state and time r...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Photochemical & photobiological sciences 2017-04, Vol.16 (4), p.539-546
Hauptverfasser: Rémy, C., Allain, C., Leray, I.
Format: Artikel
Sprache:eng
Schlagworte:
Chemical Sciences
or physical chemistry
Organic chemistry
Theoretical and
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 546
container_issue 4
container_start_page 539
container_title Photochemical & photobiological sciences
container_volume 16
creator Rémy, C.
Allain, C.
Leray, I.
description A series of π conjugated naphthalimide derivatives having an imide group as an acceptor conjugated with a methoxy arylethynyl or a methoxyphenyl triazole as a donor were prepared by Sonogashira coupling or “click” chemistry. Their photophysical properties were investigated by steady state and time resolved fluorescence spectroscopy and modelled by TD-DFT calculations. Compound Naphth-AlkyneOMe has a high fluorescence quantum yield and displays efficient photoinduced charge transfer in solution as well as in the powder state. Compound Naphth-TriazoleOMe exhibits a very high Stokes shift and its fluorescence quantum yield is low, which can be rationalized by theoretical calculations.
doi_str_mv 10.1039/c6pp00372a
format Article
fullrecord <record><control><sourceid>proquest_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_01626856v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1891879080</sourcerecordid><originalsourceid>FETCH-LOGICAL-c431t-dd2d7b858ba3c8096dbf6d1a881926acef60c0481652c44350d95214a7be97833</originalsourceid><addsrcrecordid>eNqNkbtOwzAUhi0EoqWw8AAoIxcVbMd27LGqgCJVYgAkNsuxnSZVGoc4QXTjDXklXKWUhYHp3D7959g_AKcIXiMYixvN6hrCOMFqDwwRSchYQIH3dzl9HYAj75cQIkpYcggGmCNMIBVD8Pi0rtrc-sJHqjJRnbvW1fnaF1qVUd242jZtYX3kssh-tLYy1kRfn5F21bJbqDZUlarzNldlsSqM9cfgIFOltyfbOAIvd7fP09l4_nj_MJ3Mx5rEqB0bg02ScspTFWsOBTNpxgxSnCOBmdI2Y1BDwhGjWBMSU2gExYioJLUi4XE8Ahe9btgs66ZYqWYtnSrkbDKXmx5EDDNO2TsK7HnPhve8dda3clV4bctSVdZ1XiIuEE8E5PAfKMM4rI9pQC97VDfO-8ZmuzMQlBtf5K8vAT7b6nbpypod-mNEAK56wIdRtbCNXLquqcIX_iX3DTtslto</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1862283335</pqid></control><display><type>article</type><title>Synthesis and photophysical properties of extended π conjugated naphthalimides</title><source>SpringerLink Journals - AutoHoldings</source><creator>Rémy, C. ; Allain, C. ; Leray, I.</creator><creatorcontrib>Rémy, C. ; Allain, C. ; Leray, I.</creatorcontrib><description>A series of π conjugated naphthalimide derivatives having an imide group as an acceptor conjugated with a methoxy arylethynyl or a methoxyphenyl triazole as a donor were prepared by Sonogashira coupling or “click” chemistry. Their photophysical properties were investigated by steady state and time resolved fluorescence spectroscopy and modelled by TD-DFT calculations. Compound Naphth-AlkyneOMe has a high fluorescence quantum yield and displays efficient photoinduced charge transfer in solution as well as in the powder state. Compound Naphth-TriazoleOMe exhibits a very high Stokes shift and its fluorescence quantum yield is low, which can be rationalized by theoretical calculations.</description><identifier>ISSN: 1474-905X</identifier><identifier>EISSN: 1474-9092</identifier><identifier>DOI: 10.1039/c6pp00372a</identifier><identifier>PMID: 28124059</identifier><language>eng</language><publisher>Cham: Springer International Publishing</publisher><subject>Chemical Sciences ; or physical chemistry ; Organic chemistry ; Theoretical and</subject><ispartof>Photochemical &amp; photobiological sciences, 2017-04, Vol.16 (4), p.539-546</ispartof><rights>The Royal Society of Chemistry and Owner Societies 2017</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c431t-dd2d7b858ba3c8096dbf6d1a881926acef60c0481652c44350d95214a7be97833</citedby><cites>FETCH-LOGICAL-c431t-dd2d7b858ba3c8096dbf6d1a881926acef60c0481652c44350d95214a7be97833</cites><orcidid>0000-0002-2908-264X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1039/c6pp00372a$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1039/c6pp00372a$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>230,314,780,784,885,27924,27925,41488,42557,51319</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28124059$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-01626856$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Rémy, C.</creatorcontrib><creatorcontrib>Allain, C.</creatorcontrib><creatorcontrib>Leray, I.</creatorcontrib><title>Synthesis and photophysical properties of extended π conjugated naphthalimides</title><title>Photochemical &amp; photobiological sciences</title><addtitle>Photochem Photobiol Sci</addtitle><addtitle>Photochem Photobiol Sci</addtitle><description>A series of π conjugated naphthalimide derivatives having an imide group as an acceptor conjugated with a methoxy arylethynyl or a methoxyphenyl triazole as a donor were prepared by Sonogashira coupling or “click” chemistry. Their photophysical properties were investigated by steady state and time resolved fluorescence spectroscopy and modelled by TD-DFT calculations. Compound Naphth-AlkyneOMe has a high fluorescence quantum yield and displays efficient photoinduced charge transfer in solution as well as in the powder state. Compound Naphth-TriazoleOMe exhibits a very high Stokes shift and its fluorescence quantum yield is low, which can be rationalized by theoretical calculations.</description><subject>Chemical Sciences</subject><subject>or physical chemistry</subject><subject>Organic chemistry</subject><subject>Theoretical and</subject><issn>1474-905X</issn><issn>1474-9092</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqNkbtOwzAUhi0EoqWw8AAoIxcVbMd27LGqgCJVYgAkNsuxnSZVGoc4QXTjDXklXKWUhYHp3D7959g_AKcIXiMYixvN6hrCOMFqDwwRSchYQIH3dzl9HYAj75cQIkpYcggGmCNMIBVD8Pi0rtrc-sJHqjJRnbvW1fnaF1qVUd242jZtYX3kssh-tLYy1kRfn5F21bJbqDZUlarzNldlsSqM9cfgIFOltyfbOAIvd7fP09l4_nj_MJ3Mx5rEqB0bg02ScspTFWsOBTNpxgxSnCOBmdI2Y1BDwhGjWBMSU2gExYioJLUi4XE8Ahe9btgs66ZYqWYtnSrkbDKXmx5EDDNO2TsK7HnPhve8dda3clV4bctSVdZ1XiIuEE8E5PAfKMM4rI9pQC97VDfO-8ZmuzMQlBtf5K8vAT7b6nbpypod-mNEAK56wIdRtbCNXLquqcIX_iX3DTtslto</recordid><startdate>20170401</startdate><enddate>20170401</enddate><creator>Rémy, C.</creator><creator>Allain, C.</creator><creator>Leray, I.</creator><general>Springer International Publishing</general><general>Springer</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-2908-264X</orcidid></search><sort><creationdate>20170401</creationdate><title>Synthesis and photophysical properties of extended π conjugated naphthalimides</title><author>Rémy, C. ; Allain, C. ; Leray, I.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c431t-dd2d7b858ba3c8096dbf6d1a881926acef60c0481652c44350d95214a7be97833</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Chemical Sciences</topic><topic>or physical chemistry</topic><topic>Organic chemistry</topic><topic>Theoretical and</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rémy, C.</creatorcontrib><creatorcontrib>Allain, C.</creatorcontrib><creatorcontrib>Leray, I.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Photochemical &amp; photobiological sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rémy, C.</au><au>Allain, C.</au><au>Leray, I.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and photophysical properties of extended π conjugated naphthalimides</atitle><jtitle>Photochemical &amp; photobiological sciences</jtitle><stitle>Photochem Photobiol Sci</stitle><addtitle>Photochem Photobiol Sci</addtitle><date>2017-04-01</date><risdate>2017</risdate><volume>16</volume><issue>4</issue><spage>539</spage><epage>546</epage><pages>539-546</pages><issn>1474-905X</issn><eissn>1474-9092</eissn><abstract>A series of π conjugated naphthalimide derivatives having an imide group as an acceptor conjugated with a methoxy arylethynyl or a methoxyphenyl triazole as a donor were prepared by Sonogashira coupling or “click” chemistry. Their photophysical properties were investigated by steady state and time resolved fluorescence spectroscopy and modelled by TD-DFT calculations. Compound Naphth-AlkyneOMe has a high fluorescence quantum yield and displays efficient photoinduced charge transfer in solution as well as in the powder state. Compound Naphth-TriazoleOMe exhibits a very high Stokes shift and its fluorescence quantum yield is low, which can be rationalized by theoretical calculations.</abstract><cop>Cham</cop><pub>Springer International Publishing</pub><pmid>28124059</pmid><doi>10.1039/c6pp00372a</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-2908-264X</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1474-905X
ispartof Photochemical & photobiological sciences, 2017-04, Vol.16 (4), p.539-546
issn 1474-905X
1474-9092
language eng
recordid cdi_hal_primary_oai_HAL_hal_01626856v1
source SpringerLink Journals - AutoHoldings
subjects Chemical Sciences
or physical chemistry
Organic chemistry
Theoretical and
title Synthesis and photophysical properties of extended π conjugated naphthalimides
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-20T06%3A02%3A04IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20and%20photophysical%20properties%20of%20extended%20%CF%80%20conjugated%20naphthalimides&rft.jtitle=Photochemical%20&%20photobiological%20sciences&rft.au=R%C3%A9my,%20C.&rft.date=2017-04-01&rft.volume=16&rft.issue=4&rft.spage=539&rft.epage=546&rft.pages=539-546&rft.issn=1474-905X&rft.eissn=1474-9092&rft_id=info:doi/10.1039/c6pp00372a&rft_dat=%3Cproquest_hal_p%3E1891879080%3C/proquest_hal_p%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1862283335&rft_id=info:pmid/28124059&rfr_iscdi=true