Charge transfer mediated triplet excited state formation in donor-acceptor-donor BODIPY: Application for recording of holographic structures in photopolymerizable glass

Tatsiana Mikulchyk; Safakath Karuthedath; Catherine S.P. De Castro; Andrey A. Buglak; Aimee Sheehan; Aaron Wieder; Frédéric Laquai; Izabela Naydenova; Mikhail A. Filatov

doi:10.1039/d2tc02263j

Charge transfer mediated triplet excited state formation in donor-acceptor-donor BODIPY: Application for recording of holographic structures in photopolymerizable glass

Tatsiana Mikulchyk, Safakath Karuthedath, Catherine S.P. De Castro, Andrey A. Buglak, Aimee Sheehan, Aaron Wieder, Frédéric Laquai, Izabela Naydenova, Mikhail A. Filatov^*

^*Corresponding author for this work

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

10 Scopus citations

Abstract

Donor-acceptor-donor BODIPY triads bearing anthracene or pyrene as electron donating subunits were prepared through a stepwise synthesis. Photoinduced electron transfer and formation of long-lived triplet excited states via spin-orbit charge transfer intersystem crossing (SOCT-ISC) was studied by steady-state and ultrafast pump-probe spectroscopy and further supported by DFT computations. New BODIPYs were found to form triplet states and sensitize singlet oxygen in both polar and non-polar solvents which is unusual for photosensitizers operating via SOCT-ISC. BODIPY-anthracene triad (ABA) was used as a photosensitizer component in a photopolymerizable glass that was prepared by a four-step sol-gel process. ABA in combination with N-phenylglycin (NPG) showed the ability to initiate a free-radical polymerization of methacrylate monomers under 532 nm irradiation thus allowing for holographic recording of diffractive structures. High diffraction efficiency (up to 87%) obtained for ABA-NPG containing glass as compared to a reference diiodo-BODIPY (I2BDP) demonstrates for the first time that heavy-atom-free SOCT-ISC photosensitizers can efficiently operate in the solid state.

Original language	English (US)
Pages (from-to)	11588-11597
Number of pages	10
Journal	JOURNAL OF MATERIALS CHEMISTRY C
Volume	10
Issue number	32
DOIs	https://doi.org/10.1039/d2tc02263j
State	Published - Jul 18 2022

Bibliographical note

Funding Information:
M. A. F. acknowledges TU Dublin Research Scholarship programme for the financial support of this work, Dr Alla Lemeune (ENS de Lyon) for HRMS measurements and Fred Odunjo (CREST, TU Dublin) for EDX measurements. A. A. B. acknowledges the Strategic Academic Leadership Programme “Priority 2030” of the Kazan Federal University. This publication is based on work supported by the KAUST Office of Sponsored Research (OSR) under award no. OSR-CRG2018-3746 and OSR-CRG2019-4025. C. S. P. D. C. would like to acknowledge Luis Gutiérrez-Arzaluz for help getting started with the modified microscope used for TRPL measurements.

Publisher Copyright:
© 2022 The Royal Society of Chemistry.

ASJC Scopus subject areas

General Chemistry
Materials Chemistry

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10.1039/d2tc02263j

Cite this

Mikulchyk, T., Karuthedath, S., De Castro, C. S. P., Buglak, A. A., Sheehan, A., Wieder, A., Laquai, F., Naydenova, I., & Filatov, M. A. (2022). Charge transfer mediated triplet excited state formation in donor-acceptor-donor BODIPY: Application for recording of holographic structures in photopolymerizable glass. JOURNAL OF MATERIALS CHEMISTRY C, 10(32), 11588-11597. https://doi.org/10.1039/d2tc02263j

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title = "Charge transfer mediated triplet excited state formation in donor-acceptor-donor BODIPY: Application for recording of holographic structures in photopolymerizable glass",

abstract = "Donor-acceptor-donor BODIPY triads bearing anthracene or pyrene as electron donating subunits were prepared through a stepwise synthesis. Photoinduced electron transfer and formation of long-lived triplet excited states via spin-orbit charge transfer intersystem crossing (SOCT-ISC) was studied by steady-state and ultrafast pump-probe spectroscopy and further supported by DFT computations. New BODIPYs were found to form triplet states and sensitize singlet oxygen in both polar and non-polar solvents which is unusual for photosensitizers operating via SOCT-ISC. BODIPY-anthracene triad (ABA) was used as a photosensitizer component in a photopolymerizable glass that was prepared by a four-step sol-gel process. ABA in combination with N-phenylglycin (NPG) showed the ability to initiate a free-radical polymerization of methacrylate monomers under 532 nm irradiation thus allowing for holographic recording of diffractive structures. High diffraction efficiency (up to 87%) obtained for ABA-NPG containing glass as compared to a reference diiodo-BODIPY (I2BDP) demonstrates for the first time that heavy-atom-free SOCT-ISC photosensitizers can efficiently operate in the solid state.",

author = "Tatsiana Mikulchyk and Safakath Karuthedath and {De Castro}, {Catherine S.P.} and Buglak, {Andrey A.} and Aimee Sheehan and Aaron Wieder and Fr{\'e}d{\'e}ric Laquai and Izabela Naydenova and Filatov, {Mikhail A.}",

note = "Funding Information: M. A. F. acknowledges TU Dublin Research Scholarship programme for the financial support of this work, Dr Alla Lemeune (ENS de Lyon) for HRMS measurements and Fred Odunjo (CREST, TU Dublin) for EDX measurements. A. A. B. acknowledges the Strategic Academic Leadership Programme “Priority 2030” of the Kazan Federal University. This publication is based on work supported by the KAUST Office of Sponsored Research (OSR) under award no. OSR-CRG2018-3746 and OSR-CRG2019-4025. C. S. P. D. C. would like to acknowledge Luis Guti{\'e}rrez-Arzaluz for help getting started with the modified microscope used for TRPL measurements. Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry.",

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Mikulchyk, T, Karuthedath, S, De Castro, CSP, Buglak, AA, Sheehan, A, Wieder, A, Laquai, F, Naydenova, I & Filatov, MA 2022, 'Charge transfer mediated triplet excited state formation in donor-acceptor-donor BODIPY: Application for recording of holographic structures in photopolymerizable glass', JOURNAL OF MATERIALS CHEMISTRY C, vol. 10, no. 32, pp. 11588-11597. https://doi.org/10.1039/d2tc02263j

Charge transfer mediated triplet excited state formation in donor-acceptor-donor BODIPY: Application for recording of holographic structures in photopolymerizable glass. / Mikulchyk, Tatsiana; Karuthedath, Safakath; De Castro, Catherine S.P. et al.
In: JOURNAL OF MATERIALS CHEMISTRY C, Vol. 10, No. 32, 18.07.2022, p. 11588-11597.

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

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T1 - Charge transfer mediated triplet excited state formation in donor-acceptor-donor BODIPY

T2 - Application for recording of holographic structures in photopolymerizable glass

AU - Mikulchyk, Tatsiana

AU - Karuthedath, Safakath

AU - De Castro, Catherine S.P.

AU - Buglak, Andrey A.

AU - Sheehan, Aimee

AU - Wieder, Aaron

AU - Laquai, Frédéric

AU - Naydenova, Izabela

AU - Filatov, Mikhail A.

N1 - Funding Information: M. A. F. acknowledges TU Dublin Research Scholarship programme for the financial support of this work, Dr Alla Lemeune (ENS de Lyon) for HRMS measurements and Fred Odunjo (CREST, TU Dublin) for EDX measurements. A. A. B. acknowledges the Strategic Academic Leadership Programme “Priority 2030” of the Kazan Federal University. This publication is based on work supported by the KAUST Office of Sponsored Research (OSR) under award no. OSR-CRG2018-3746 and OSR-CRG2019-4025. C. S. P. D. C. would like to acknowledge Luis Gutiérrez-Arzaluz for help getting started with the modified microscope used for TRPL measurements. Publisher Copyright: © 2022 The Royal Society of Chemistry.

PY - 2022/7/18

Y1 - 2022/7/18

N2 - Donor-acceptor-donor BODIPY triads bearing anthracene or pyrene as electron donating subunits were prepared through a stepwise synthesis. Photoinduced electron transfer and formation of long-lived triplet excited states via spin-orbit charge transfer intersystem crossing (SOCT-ISC) was studied by steady-state and ultrafast pump-probe spectroscopy and further supported by DFT computations. New BODIPYs were found to form triplet states and sensitize singlet oxygen in both polar and non-polar solvents which is unusual for photosensitizers operating via SOCT-ISC. BODIPY-anthracene triad (ABA) was used as a photosensitizer component in a photopolymerizable glass that was prepared by a four-step sol-gel process. ABA in combination with N-phenylglycin (NPG) showed the ability to initiate a free-radical polymerization of methacrylate monomers under 532 nm irradiation thus allowing for holographic recording of diffractive structures. High diffraction efficiency (up to 87%) obtained for ABA-NPG containing glass as compared to a reference diiodo-BODIPY (I2BDP) demonstrates for the first time that heavy-atom-free SOCT-ISC photosensitizers can efficiently operate in the solid state.

AB - Donor-acceptor-donor BODIPY triads bearing anthracene or pyrene as electron donating subunits were prepared through a stepwise synthesis. Photoinduced electron transfer and formation of long-lived triplet excited states via spin-orbit charge transfer intersystem crossing (SOCT-ISC) was studied by steady-state and ultrafast pump-probe spectroscopy and further supported by DFT computations. New BODIPYs were found to form triplet states and sensitize singlet oxygen in both polar and non-polar solvents which is unusual for photosensitizers operating via SOCT-ISC. BODIPY-anthracene triad (ABA) was used as a photosensitizer component in a photopolymerizable glass that was prepared by a four-step sol-gel process. ABA in combination with N-phenylglycin (NPG) showed the ability to initiate a free-radical polymerization of methacrylate monomers under 532 nm irradiation thus allowing for holographic recording of diffractive structures. High diffraction efficiency (up to 87%) obtained for ABA-NPG containing glass as compared to a reference diiodo-BODIPY (I2BDP) demonstrates for the first time that heavy-atom-free SOCT-ISC photosensitizers can efficiently operate in the solid state.

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Charge transfer mediated triplet excited state formation in donor-acceptor-donor BODIPY: Application for recording of holographic structures in photopolymerizable glass

Abstract

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