Exciplex Emission from a Boron Dipyrromethene (Bodipy) Dye Equipped with a Dicyanovinyl Appendage
The photophysical properties of a prototypic donor–acceptor dyad, featuring a conventional boron dipyrromethene (Bodipy) dye linked to a dicyanovinyl unit through a meso‐phenylene ring, have been recorded in weakly polar solvents. The absorption spectrum remains unperturbed relative to that of the p...
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| creator | Nano, Adela Ziessel, Raymond Stachelek, Patrycja Alamiry, Mohammed A. H. Harriman, Anthony |
| description | The photophysical properties of a prototypic donor–acceptor dyad, featuring a conventional boron dipyrromethene (Bodipy) dye linked to a dicyanovinyl unit through a meso‐phenylene ring, have been recorded in weakly polar solvents. The absorption spectrum remains unperturbed relative to that of the parent Bodipy dye but the fluorescence is extensively quenched. At room temperature, the emission spectrum comprises roughly equal contributions from the regular π, π* excited‐singlet state and from an exciplex formed by partial charge transfer from Bodipy to the dicyanovinyl residue. This mixture moves progressively in favor of the locally excited π, π* state on cooling and the exciplex is no longer seen in frozen media; the overall emission quantum yield changes dramatically near the freezing point of the solvent. The exciplex, which has a lifetime of approximately 1 ns at room temperature, can also be seen by transient absorption spectroscopy, in which it decays to form the locally excited triplet state. Under applied pressure (P |
| doi_str_mv | 10.1002/cphc.201300805 |
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Dual emission of the target dyad is pressure sensitive in weakly polar solvents (see picture) and also susceptible to changes in temperature and local polarity. This behavior can be traced to the interplay between π, π* fluorescence and emission from an intramolecular exciplex. The two species exhibit comparable emission quantum yields under ambient conditions but formation of the exciplex is influenced by the local environment.</description><identifier>ISSN: 1439-4235</identifier><identifier>EISSN: 1439-7641</identifier><identifier>DOI: 10.1002/cphc.201300805</identifier><identifier>PMID: 24376111</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Atomic and molecular physics ; donor-acceptor systems ; dyes/pigments ; Exact sciences and technology ; exciplexes ; fluorescence ; Fluorescence and phosphorescence spectra ; Fluorescence and phosphorescence; radiationless transitions, quenching (intersystem crossing, internal conversion) ; Molecular properties and interactions with photons ; photophysics ; Physics ; Spectrum analysis</subject><ispartof>Chemphyschem, 2014-01, Vol.15 (1), p.177-186</ispartof><rights>Copyright © 2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4785-3c070d06c84ffa1cbd74728c05c532eb0fd1a4498aed47680500fb84781af7123</citedby><cites>FETCH-LOGICAL-c4785-3c070d06c84ffa1cbd74728c05c532eb0fd1a4498aed47680500fb84781af7123</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcphc.201300805$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcphc.201300805$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=28094080$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24376111$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nano, Adela</creatorcontrib><creatorcontrib>Ziessel, Raymond</creatorcontrib><creatorcontrib>Stachelek, Patrycja</creatorcontrib><creatorcontrib>Alamiry, Mohammed A. H.</creatorcontrib><creatorcontrib>Harriman, Anthony</creatorcontrib><title>Exciplex Emission from a Boron Dipyrromethene (Bodipy) Dye Equipped with a Dicyanovinyl Appendage</title><title>Chemphyschem</title><addtitle>ChemPhysChem</addtitle><description>The photophysical properties of a prototypic donor–acceptor dyad, featuring a conventional boron dipyrromethene (Bodipy) dye linked to a dicyanovinyl unit through a meso‐phenylene ring, have been recorded in weakly polar solvents. The absorption spectrum remains unperturbed relative to that of the parent Bodipy dye but the fluorescence is extensively quenched. At room temperature, the emission spectrum comprises roughly equal contributions from the regular π, π* excited‐singlet state and from an exciplex formed by partial charge transfer from Bodipy to the dicyanovinyl residue. This mixture moves progressively in favor of the locally excited π, π* state on cooling and the exciplex is no longer seen in frozen media; the overall emission quantum yield changes dramatically near the freezing point of the solvent. The exciplex, which has a lifetime of approximately 1 ns at room temperature, can also be seen by transient absorption spectroscopy, in which it decays to form the locally excited triplet state. Under applied pressure (P<170 MPa), formation of the exciplex is somewhat hindered by restricted rotation around the semirigid linkage and again the emission profile shifts in favor of the π, π* excited state. At higher pressure (170<P<550 MPa), the molecule undergoes reversible distortion that has a small effect on the yield of π, π* emission but severely quenches exciplex fluorescence. In the limiting case, this high‐pressure effect decreases the molar volume of the solute by approximately 25 cm3 and opens a new channel for nonradiative deactivation of the excited‐state manifold.
Dual emission of the target dyad is pressure sensitive in weakly polar solvents (see picture) and also susceptible to changes in temperature and local polarity. This behavior can be traced to the interplay between π, π* fluorescence and emission from an intramolecular exciplex. The two species exhibit comparable emission quantum yields under ambient conditions but formation of the exciplex is influenced by the local environment.</description><subject>Atomic and molecular physics</subject><subject>donor-acceptor systems</subject><subject>dyes/pigments</subject><subject>Exact sciences and technology</subject><subject>exciplexes</subject><subject>fluorescence</subject><subject>Fluorescence and phosphorescence spectra</subject><subject>Fluorescence and phosphorescence; radiationless transitions, quenching (intersystem crossing, internal conversion)</subject><subject>Molecular properties and interactions with photons</subject><subject>photophysics</subject><subject>Physics</subject><subject>Spectrum analysis</subject><issn>1439-4235</issn><issn>1439-7641</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkMFv0zAUxi3ExEbHlSOyhJC2Q7rn2ImT49Z03aRq7FAEN8t1bOqRxpndsOa_x1VLQVw42X7-fd9770PoPYExAUivVLdS4xQIBSgge4XOCKNlwnNGXh_uLKXZKXobwhPsGE7eoNOUUZ4TQs6QnG6V7Rq9xdO1DcG6Fhvv1ljiG-fjo7Ld4GNBb1a61fjixtWxcomrQePpc2-7Ttf4xW5WUVFZNcjW_bTt0ODr-NPW8rs-RydGNkG_O5wj9OV2upjcJfPPs_vJ9TxRjBdZQhVwqCFXBTNGErWsOeNpoSBTGU31EkxNJGNlIXXNeB6XBTDLImqJNJykdIQu9r6dd8-9DhsRF1K6aWSrXR8EYWVcPivLPKIf_0GfXO_bOF2keAY55THRERrvKeVdCF4b0Xm7ln4QBMQufLELXxzDj4IPB9t-udb1Ef-ddgQ-HQAZlGyMl62y4Q9XQMmiU-TKPfdiGz38p62YPN5N_h4i2Wtt2OjtUSv9D5FzyjPx9WEmZouHavGtmotH-gsHKKt8</recordid><startdate>20140113</startdate><enddate>20140113</enddate><creator>Nano, Adela</creator><creator>Ziessel, Raymond</creator><creator>Stachelek, Patrycja</creator><creator>Alamiry, Mohammed A. H.</creator><creator>Harriman, Anthony</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20140113</creationdate><title>Exciplex Emission from a Boron Dipyrromethene (Bodipy) Dye Equipped with a Dicyanovinyl Appendage</title><author>Nano, Adela ; Ziessel, Raymond ; Stachelek, Patrycja ; Alamiry, Mohammed A. H. ; Harriman, Anthony</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4785-3c070d06c84ffa1cbd74728c05c532eb0fd1a4498aed47680500fb84781af7123</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Atomic and molecular physics</topic><topic>donor-acceptor systems</topic><topic>dyes/pigments</topic><topic>Exact sciences and technology</topic><topic>exciplexes</topic><topic>fluorescence</topic><topic>Fluorescence and phosphorescence spectra</topic><topic>Fluorescence and phosphorescence; radiationless transitions, quenching (intersystem crossing, internal conversion)</topic><topic>Molecular properties and interactions with photons</topic><topic>photophysics</topic><topic>Physics</topic><topic>Spectrum analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nano, Adela</creatorcontrib><creatorcontrib>Ziessel, Raymond</creatorcontrib><creatorcontrib>Stachelek, Patrycja</creatorcontrib><creatorcontrib>Alamiry, Mohammed A. H.</creatorcontrib><creatorcontrib>Harriman, Anthony</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemphyschem</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nano, Adela</au><au>Ziessel, Raymond</au><au>Stachelek, Patrycja</au><au>Alamiry, Mohammed A. H.</au><au>Harriman, Anthony</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Exciplex Emission from a Boron Dipyrromethene (Bodipy) Dye Equipped with a Dicyanovinyl Appendage</atitle><jtitle>Chemphyschem</jtitle><addtitle>ChemPhysChem</addtitle><date>2014-01-13</date><risdate>2014</risdate><volume>15</volume><issue>1</issue><spage>177</spage><epage>186</epage><pages>177-186</pages><issn>1439-4235</issn><eissn>1439-7641</eissn><abstract>The photophysical properties of a prototypic donor–acceptor dyad, featuring a conventional boron dipyrromethene (Bodipy) dye linked to a dicyanovinyl unit through a meso‐phenylene ring, have been recorded in weakly polar solvents. The absorption spectrum remains unperturbed relative to that of the parent Bodipy dye but the fluorescence is extensively quenched. At room temperature, the emission spectrum comprises roughly equal contributions from the regular π, π* excited‐singlet state and from an exciplex formed by partial charge transfer from Bodipy to the dicyanovinyl residue. This mixture moves progressively in favor of the locally excited π, π* state on cooling and the exciplex is no longer seen in frozen media; the overall emission quantum yield changes dramatically near the freezing point of the solvent. The exciplex, which has a lifetime of approximately 1 ns at room temperature, can also be seen by transient absorption spectroscopy, in which it decays to form the locally excited triplet state. Under applied pressure (P<170 MPa), formation of the exciplex is somewhat hindered by restricted rotation around the semirigid linkage and again the emission profile shifts in favor of the π, π* excited state. At higher pressure (170<P<550 MPa), the molecule undergoes reversible distortion that has a small effect on the yield of π, π* emission but severely quenches exciplex fluorescence. In the limiting case, this high‐pressure effect decreases the molar volume of the solute by approximately 25 cm3 and opens a new channel for nonradiative deactivation of the excited‐state manifold.
Dual emission of the target dyad is pressure sensitive in weakly polar solvents (see picture) and also susceptible to changes in temperature and local polarity. This behavior can be traced to the interplay between π, π* fluorescence and emission from an intramolecular exciplex. The two species exhibit comparable emission quantum yields under ambient conditions but formation of the exciplex is influenced by the local environment.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>24376111</pmid><doi>10.1002/cphc.201300805</doi><tpages>10</tpages></addata></record> |
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| subjects | Atomic and molecular physics donor-acceptor systems dyes/pigments Exact sciences and technology exciplexes fluorescence Fluorescence and phosphorescence spectra Fluorescence and phosphorescence radiationless transitions, quenching (intersystem crossing, internal conversion) Molecular properties and interactions with photons photophysics Physics Spectrum analysis |
| title | Exciplex Emission from a Boron Dipyrromethene (Bodipy) Dye Equipped with a Dicyanovinyl Appendage |
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