Loading…

Unravelling the ultrafast dynamics of a N-BODIPY compound

Although the photophysics of BODIPY compounds has been widely investigated in the last few years, their analogues N-BODIPY, with nitrogen substitution at the boron center, did not receive comparable attention. In this work we report the synthesis and photochemical characterization of a substituted N...

Full description

Saved in:
Bibliographic Details
Published in:Dyes and pigments 2022-04, Vol.200, p.110181, Article 110181
Main Authors: Doria, Sandra, Taddei, Maria, Cupellini, Lorenzo, Biagiotti, Giacomo, Bartolini, Paolo, Bussotti, Laura, Cicchi, Stefano, Foggi, Paolo, Mennucci, Benedetta, Di Donato, Mariangela
Format: Article
Language:English
Subjects:
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c352t-13b45a9d9ea8b34a4c0ad7184ba95eec4fbe5c69fbcf204a0861af8e2acbb9e13
cites cdi_FETCH-LOGICAL-c352t-13b45a9d9ea8b34a4c0ad7184ba95eec4fbe5c69fbcf204a0861af8e2acbb9e13
container_end_page
container_issue
container_start_page 110181
container_title Dyes and pigments
container_volume 200
creator Doria, Sandra
Taddei, Maria
Cupellini, Lorenzo
Biagiotti, Giacomo
Bartolini, Paolo
Bussotti, Laura
Cicchi, Stefano
Foggi, Paolo
Mennucci, Benedetta
Di Donato, Mariangela
description Although the photophysics of BODIPY compounds has been widely investigated in the last few years, their analogues N-BODIPY, with nitrogen substitution at the boron center, did not receive comparable attention. In this work we report the synthesis and photochemical characterization of a substituted N-BODIPY compound, by means of a combined theoretical and spectroscopic approach. Compared to a standard BODIPY, the compound under investigation presents a lower fluorescence quantum yield (QY) in the visible region. The excited state relaxation dynamics of the dye was studied in different solvents, showing further fluorescence quenching in polar solvents, and excited state decay rates strongly dependent on the environment polarity. The role of the pendant moieties and the involvement of charge transfer states in the excited state dynamics was experimentally addressed by transient absorption spectroscopy, and further analyzed with TD-DFT calculations, which allowed precise assignment of the transient signals to the correspondent electronic configuration. The complete picture of the N-BODIPY behavior shows the presence of both charge transfer and localized states, influencing the observed photophysics to different amounts, depending on the excitation conditions and the surrounding environment. •Ultrafast behavior of N-BODIPY.•Fluorescence emission in UV region from S2 electronic state.•Computational and spectroscopic methods identify charge transfer and localized states.•Fluorescence quenching in polar solvents.
doi_str_mv 10.1016/j.dyepig.2022.110181
format article
fullrecord <record><control><sourceid>elsevier_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1016_j_dyepig_2022_110181</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0143720822001036</els_id><sourcerecordid>S0143720822001036</sourcerecordid><originalsourceid>FETCH-LOGICAL-c352t-13b45a9d9ea8b34a4c0ad7184ba95eec4fbe5c69fbcf204a0861af8e2acbb9e13</originalsourceid><addsrcrecordid>eNp9j81KAzEUhYMoWKtv4CIvMGP-ppPZCFqtFop1YReuwk3mpqZMZ0oyLfTtbRnXrg4cOB_nI-Ses5wzPnnY5PURd2GdCyZEzk-d5hdkxHUpM1kqeUlGjCuZlYLpa3KT0oYxpqXgI1Kt2ggHbJrQrmn_g3Tf9BE8pJ7Wxxa2wSXaeQr0I3tevsw_v6nrtrtu39a35MpDk_DuL8dkNXv9mr5ni-XbfPq0yJwsRJ9xaVUBVV0haCsVKMegLrlWFqoC0SlvsXCTylvnBVPA9ISD1yjAWVshl2OiBq6LXUoRvdnFsIV4NJyZs77ZmEHfnPXNoH-aPQ4zPH07BIwmuYCtwzpEdL2pu_A_4BcO02Wm</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Unravelling the ultrafast dynamics of a N-BODIPY compound</title><source>ScienceDirect Journals</source><creator>Doria, Sandra ; Taddei, Maria ; Cupellini, Lorenzo ; Biagiotti, Giacomo ; Bartolini, Paolo ; Bussotti, Laura ; Cicchi, Stefano ; Foggi, Paolo ; Mennucci, Benedetta ; Di Donato, Mariangela</creator><creatorcontrib>Doria, Sandra ; Taddei, Maria ; Cupellini, Lorenzo ; Biagiotti, Giacomo ; Bartolini, Paolo ; Bussotti, Laura ; Cicchi, Stefano ; Foggi, Paolo ; Mennucci, Benedetta ; Di Donato, Mariangela</creatorcontrib><description>Although the photophysics of BODIPY compounds has been widely investigated in the last few years, their analogues N-BODIPY, with nitrogen substitution at the boron center, did not receive comparable attention. In this work we report the synthesis and photochemical characterization of a substituted N-BODIPY compound, by means of a combined theoretical and spectroscopic approach. Compared to a standard BODIPY, the compound under investigation presents a lower fluorescence quantum yield (QY) in the visible region. The excited state relaxation dynamics of the dye was studied in different solvents, showing further fluorescence quenching in polar solvents, and excited state decay rates strongly dependent on the environment polarity. The role of the pendant moieties and the involvement of charge transfer states in the excited state dynamics was experimentally addressed by transient absorption spectroscopy, and further analyzed with TD-DFT calculations, which allowed precise assignment of the transient signals to the correspondent electronic configuration. The complete picture of the N-BODIPY behavior shows the presence of both charge transfer and localized states, influencing the observed photophysics to different amounts, depending on the excitation conditions and the surrounding environment. •Ultrafast behavior of N-BODIPY.•Fluorescence emission in UV region from S2 electronic state.•Computational and spectroscopic methods identify charge transfer and localized states.•Fluorescence quenching in polar solvents.</description><identifier>ISSN: 0143-7208</identifier><identifier>EISSN: 1873-3743</identifier><identifier>DOI: 10.1016/j.dyepig.2022.110181</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Charge transfer states ; DFT computations ; N-BODIPY ; Transient absorption spectroscopy</subject><ispartof>Dyes and pigments, 2022-04, Vol.200, p.110181, Article 110181</ispartof><rights>2022 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c352t-13b45a9d9ea8b34a4c0ad7184ba95eec4fbe5c69fbcf204a0861af8e2acbb9e13</citedby><cites>FETCH-LOGICAL-c352t-13b45a9d9ea8b34a4c0ad7184ba95eec4fbe5c69fbcf204a0861af8e2acbb9e13</cites><orcidid>0000-0002-6596-7031 ; 0000-0002-9440-1643 ; 0000-0003-0848-2908</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Doria, Sandra</creatorcontrib><creatorcontrib>Taddei, Maria</creatorcontrib><creatorcontrib>Cupellini, Lorenzo</creatorcontrib><creatorcontrib>Biagiotti, Giacomo</creatorcontrib><creatorcontrib>Bartolini, Paolo</creatorcontrib><creatorcontrib>Bussotti, Laura</creatorcontrib><creatorcontrib>Cicchi, Stefano</creatorcontrib><creatorcontrib>Foggi, Paolo</creatorcontrib><creatorcontrib>Mennucci, Benedetta</creatorcontrib><creatorcontrib>Di Donato, Mariangela</creatorcontrib><title>Unravelling the ultrafast dynamics of a N-BODIPY compound</title><title>Dyes and pigments</title><description>Although the photophysics of BODIPY compounds has been widely investigated in the last few years, their analogues N-BODIPY, with nitrogen substitution at the boron center, did not receive comparable attention. In this work we report the synthesis and photochemical characterization of a substituted N-BODIPY compound, by means of a combined theoretical and spectroscopic approach. Compared to a standard BODIPY, the compound under investigation presents a lower fluorescence quantum yield (QY) in the visible region. The excited state relaxation dynamics of the dye was studied in different solvents, showing further fluorescence quenching in polar solvents, and excited state decay rates strongly dependent on the environment polarity. The role of the pendant moieties and the involvement of charge transfer states in the excited state dynamics was experimentally addressed by transient absorption spectroscopy, and further analyzed with TD-DFT calculations, which allowed precise assignment of the transient signals to the correspondent electronic configuration. The complete picture of the N-BODIPY behavior shows the presence of both charge transfer and localized states, influencing the observed photophysics to different amounts, depending on the excitation conditions and the surrounding environment. •Ultrafast behavior of N-BODIPY.•Fluorescence emission in UV region from S2 electronic state.•Computational and spectroscopic methods identify charge transfer and localized states.•Fluorescence quenching in polar solvents.</description><subject>Charge transfer states</subject><subject>DFT computations</subject><subject>N-BODIPY</subject><subject>Transient absorption spectroscopy</subject><issn>0143-7208</issn><issn>1873-3743</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp9j81KAzEUhYMoWKtv4CIvMGP-ppPZCFqtFop1YReuwk3mpqZMZ0oyLfTtbRnXrg4cOB_nI-Ses5wzPnnY5PURd2GdCyZEzk-d5hdkxHUpM1kqeUlGjCuZlYLpa3KT0oYxpqXgI1Kt2ggHbJrQrmn_g3Tf9BE8pJ7Wxxa2wSXaeQr0I3tevsw_v6nrtrtu39a35MpDk_DuL8dkNXv9mr5ni-XbfPq0yJwsRJ9xaVUBVV0haCsVKMegLrlWFqoC0SlvsXCTylvnBVPA9ISD1yjAWVshl2OiBq6LXUoRvdnFsIV4NJyZs77ZmEHfnPXNoH-aPQ4zPH07BIwmuYCtwzpEdL2pu_A_4BcO02Wm</recordid><startdate>202204</startdate><enddate>202204</enddate><creator>Doria, Sandra</creator><creator>Taddei, Maria</creator><creator>Cupellini, Lorenzo</creator><creator>Biagiotti, Giacomo</creator><creator>Bartolini, Paolo</creator><creator>Bussotti, Laura</creator><creator>Cicchi, Stefano</creator><creator>Foggi, Paolo</creator><creator>Mennucci, Benedetta</creator><creator>Di Donato, Mariangela</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-6596-7031</orcidid><orcidid>https://orcid.org/0000-0002-9440-1643</orcidid><orcidid>https://orcid.org/0000-0003-0848-2908</orcidid></search><sort><creationdate>202204</creationdate><title>Unravelling the ultrafast dynamics of a N-BODIPY compound</title><author>Doria, Sandra ; Taddei, Maria ; Cupellini, Lorenzo ; Biagiotti, Giacomo ; Bartolini, Paolo ; Bussotti, Laura ; Cicchi, Stefano ; Foggi, Paolo ; Mennucci, Benedetta ; Di Donato, Mariangela</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c352t-13b45a9d9ea8b34a4c0ad7184ba95eec4fbe5c69fbcf204a0861af8e2acbb9e13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Charge transfer states</topic><topic>DFT computations</topic><topic>N-BODIPY</topic><topic>Transient absorption spectroscopy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Doria, Sandra</creatorcontrib><creatorcontrib>Taddei, Maria</creatorcontrib><creatorcontrib>Cupellini, Lorenzo</creatorcontrib><creatorcontrib>Biagiotti, Giacomo</creatorcontrib><creatorcontrib>Bartolini, Paolo</creatorcontrib><creatorcontrib>Bussotti, Laura</creatorcontrib><creatorcontrib>Cicchi, Stefano</creatorcontrib><creatorcontrib>Foggi, Paolo</creatorcontrib><creatorcontrib>Mennucci, Benedetta</creatorcontrib><creatorcontrib>Di Donato, Mariangela</creatorcontrib><collection>CrossRef</collection><jtitle>Dyes and pigments</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Doria, Sandra</au><au>Taddei, Maria</au><au>Cupellini, Lorenzo</au><au>Biagiotti, Giacomo</au><au>Bartolini, Paolo</au><au>Bussotti, Laura</au><au>Cicchi, Stefano</au><au>Foggi, Paolo</au><au>Mennucci, Benedetta</au><au>Di Donato, Mariangela</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Unravelling the ultrafast dynamics of a N-BODIPY compound</atitle><jtitle>Dyes and pigments</jtitle><date>2022-04</date><risdate>2022</risdate><volume>200</volume><spage>110181</spage><pages>110181-</pages><artnum>110181</artnum><issn>0143-7208</issn><eissn>1873-3743</eissn><abstract>Although the photophysics of BODIPY compounds has been widely investigated in the last few years, their analogues N-BODIPY, with nitrogen substitution at the boron center, did not receive comparable attention. In this work we report the synthesis and photochemical characterization of a substituted N-BODIPY compound, by means of a combined theoretical and spectroscopic approach. Compared to a standard BODIPY, the compound under investigation presents a lower fluorescence quantum yield (QY) in the visible region. The excited state relaxation dynamics of the dye was studied in different solvents, showing further fluorescence quenching in polar solvents, and excited state decay rates strongly dependent on the environment polarity. The role of the pendant moieties and the involvement of charge transfer states in the excited state dynamics was experimentally addressed by transient absorption spectroscopy, and further analyzed with TD-DFT calculations, which allowed precise assignment of the transient signals to the correspondent electronic configuration. The complete picture of the N-BODIPY behavior shows the presence of both charge transfer and localized states, influencing the observed photophysics to different amounts, depending on the excitation conditions and the surrounding environment. •Ultrafast behavior of N-BODIPY.•Fluorescence emission in UV region from S2 electronic state.•Computational and spectroscopic methods identify charge transfer and localized states.•Fluorescence quenching in polar solvents.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.dyepig.2022.110181</doi><orcidid>https://orcid.org/0000-0002-6596-7031</orcidid><orcidid>https://orcid.org/0000-0002-9440-1643</orcidid><orcidid>https://orcid.org/0000-0003-0848-2908</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 0143-7208
ispartof Dyes and pigments, 2022-04, Vol.200, p.110181, Article 110181
issn 0143-7208
1873-3743
language eng
recordid cdi_crossref_primary_10_1016_j_dyepig_2022_110181
source ScienceDirect Journals
subjects Charge transfer states
DFT computations
N-BODIPY
Transient absorption spectroscopy
title Unravelling the ultrafast dynamics of a N-BODIPY compound
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T22%3A32%3A55IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-elsevier_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Unravelling%20the%20ultrafast%20dynamics%20of%20a%20N-BODIPY%20compound&rft.jtitle=Dyes%20and%20pigments&rft.au=Doria,%20Sandra&rft.date=2022-04&rft.volume=200&rft.spage=110181&rft.pages=110181-&rft.artnum=110181&rft.issn=0143-7208&rft.eissn=1873-3743&rft_id=info:doi/10.1016/j.dyepig.2022.110181&rft_dat=%3Celsevier_cross%3ES0143720822001036%3C/elsevier_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c352t-13b45a9d9ea8b34a4c0ad7184ba95eec4fbe5c69fbcf204a0861af8e2acbb9e13%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true