BODIPY-pyrene and perylene dyads as heavy atom-free singlet oxygen sensitizers

Mikhail A. Filatov; Safakath Karuthedath; Pavel M. Polestshuk; Susan Callaghan; Keith J. Flanagan; Thomas Wiesner; Frédéric Laquai; Mathias O. Senge

doi:10.1002/cptc.201800020

BODIPY-pyrene and perylene dyads as heavy atom-free singlet oxygen sensitizers

Mikhail A. Filatov, Safakath Karuthedath, Pavel M. Polestshuk, Susan Callaghan, Keith J. Flanagan, Thomas Wiesner, Frédéric Laquai, Mathias O. Senge

Research output: Contribution to journal › Article › peer-review

76 Scopus citations

Abstract

Dyads combining BODIPY as an electron acceptor and pyrene or perylene as electron donor subunits were prepared and studied their photophysical properties studied by steady-state and transient spectroscopy. Depending on the structure of the subunits and polarity of the media, the dyads show either bright fluorescence or photo-induced electron transfer (PeT) in solution. Charge-transfer (CT) states formed as a result of PeT and were found to yield triplet excited states of the BODIPY. In the presence of molecular oxygen, the dyads sensitize singlet oxygen (1O2) with quantum yields of up to 0.75.

Original language	English (US)
Pages (from-to)	606-615
Number of pages	10
Journal	ChemPhotoChem
Volume	2
Issue number	7
DOIs	https://doi.org/10.1002/cptc.201800020
State	Published - Mar 23 2018

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: This work was supported by grants from the European Commission (CONSORT, Grant No. 655142), Science Foundation Ireland (SFI IvP 13/IA/1894) and the Irish Research Council (GOIPG/2016/1250). The research reported in this publication was supported by funding from King Abdullah University of Science and Technology (KAUST).

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10.1002/cptc.201800020

https://repository.kaust.edu.sa/bitstream/10754/627212/1/Filatov_et_al-2018-ChemPhotoChem.pdf

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@article{eb8d8a3687c044559d630239068837b7,

title = "BODIPY-pyrene and perylene dyads as heavy atom-free singlet oxygen sensitizers",

abstract = "Dyads combining BODIPY as an electron acceptor and pyrene or perylene as electron donor subunits were prepared and studied their photophysical properties studied by steady-state and transient spectroscopy. Depending on the structure of the subunits and polarity of the media, the dyads show either bright fluorescence or photo-induced electron transfer (PeT) in solution. Charge-transfer (CT) states formed as a result of PeT and were found to yield triplet excited states of the BODIPY. In the presence of molecular oxygen, the dyads sensitize singlet oxygen (1O2) with quantum yields of up to 0.75.",

author = "Filatov, {Mikhail A.} and Safakath Karuthedath and Polestshuk, {Pavel M.} and Susan Callaghan and Flanagan, {Keith J.} and Thomas Wiesner and Fr{\'e}d{\'e}ric Laquai and Senge, {Mathias O.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported by grants from the European Commission (CONSORT, Grant No. 655142), Science Foundation Ireland (SFI IvP 13/IA/1894) and the Irish Research Council (GOIPG/2016/1250). The research reported in this publication was supported by funding from King Abdullah University of Science and Technology (KAUST).",

year = "2018",

month = mar,

day = "23",

doi = "10.1002/cptc.201800020",

language = "English (US)",

volume = "2",

pages = "606--615",

journal = "ChemPhotoChem",

issn = "2367-0932",

publisher = "Wiley-VCH Verlag",

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TY - JOUR

T1 - BODIPY-pyrene and perylene dyads as heavy atom-free singlet oxygen sensitizers

AU - Filatov, Mikhail A.

AU - Karuthedath, Safakath

AU - Polestshuk, Pavel M.

AU - Callaghan, Susan

AU - Flanagan, Keith J.

AU - Wiesner, Thomas

AU - Laquai, Frédéric

AU - Senge, Mathias O.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported by grants from the European Commission (CONSORT, Grant No. 655142), Science Foundation Ireland (SFI IvP 13/IA/1894) and the Irish Research Council (GOIPG/2016/1250). The research reported in this publication was supported by funding from King Abdullah University of Science and Technology (KAUST).

PY - 2018/3/23

Y1 - 2018/3/23

N2 - Dyads combining BODIPY as an electron acceptor and pyrene or perylene as electron donor subunits were prepared and studied their photophysical properties studied by steady-state and transient spectroscopy. Depending on the structure of the subunits and polarity of the media, the dyads show either bright fluorescence or photo-induced electron transfer (PeT) in solution. Charge-transfer (CT) states formed as a result of PeT and were found to yield triplet excited states of the BODIPY. In the presence of molecular oxygen, the dyads sensitize singlet oxygen (1O2) with quantum yields of up to 0.75.

AB - Dyads combining BODIPY as an electron acceptor and pyrene or perylene as electron donor subunits were prepared and studied their photophysical properties studied by steady-state and transient spectroscopy. Depending on the structure of the subunits and polarity of the media, the dyads show either bright fluorescence or photo-induced electron transfer (PeT) in solution. Charge-transfer (CT) states formed as a result of PeT and were found to yield triplet excited states of the BODIPY. In the presence of molecular oxygen, the dyads sensitize singlet oxygen (1O2) with quantum yields of up to 0.75.

UR - http://hdl.handle.net/10754/627212

UR - http://onlinelibrary.wiley.com/doi/10.1002/cptc.201800020/abstract

U2 - 10.1002/cptc.201800020

DO - 10.1002/cptc.201800020

M3 - Article

SN - 2367-0932

VL - 2

SP - 606

EP - 615

JO - ChemPhotoChem

JF - ChemPhotoChem

IS - 7

ER -

BODIPY-pyrene and perylene dyads as heavy atom-free singlet oxygen sensitizers

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CCDC 1819152: Experimental Crystal Structure Determination : 2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-10-(pyren-1-yl)-5H-4lambda5,5lambda5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

CCDC 1819153: Experimental Crystal Structure Determination : 2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-10-(perylen-3-yl)-5H-6lambda5,5lambda5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

CCDC 1819150: Experimental Crystal Structure Determination : 5,5-difluoro-10-(pyren-1-yl)-5H-6lambda5,5lambda5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

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BODIPY-pyrene and perylene dyads as heavy atom-free singlet oxygen sensitizers

Abstract

Bibliographical note

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CCDC 1819152: Experimental Crystal Structure Determination : 2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-10-(pyren-1-yl)-5H-4lambda5,5lambda5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

CCDC 1819153: Experimental Crystal Structure Determination : 2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-10-(perylen-3-yl)-5H-6lambda5,5lambda5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

CCDC 1819150: Experimental Crystal Structure Determination : 5,5-difluoro-10-(pyren-1-yl)-5H-6lambda5,5lambda5-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

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