Fully Conjugated Pyrene-BODIPY and Pyrene-BODIPY-Ferrocene Dyads and Triads: Synthesis, Characterization, and Selective Noncovalent Interactions with Nanocarbon Materials

Yuriy V. Zatsikha; Tanner S. Blesener; Alex J. King; Andrew T. Healy; Philip C. Goff; Natalia O. Didukh; David A. Blank; Yuriy P. Kovtun; Victor N. Nemykin

doi:10.1021/acs.jpcb.0c10074

Fully Conjugated Pyrene-BODIPY and Pyrene-BODIPY-Ferrocene Dyads and Triads: Synthesis, Characterization, and Selective Noncovalent Interactions with Nanocarbon Materials

Yuriy V. Zatsikha, Tanner S. Blesener, Alex J. King, Andrew T. Healy, Philip C. Goff, Natalia O. Didukh, David A. Blank, Yuriy P. Kovtun, Victor N. Nemykin

Chemistry (Twin Cities)

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

14 Scopus citations

Abstract

Several pyrene-boron-dipyrromethene (BODIPY) and pyrene-BODIPY-ferrocene derivatives with a fully conjugated pyrene fragment appended to the α-position(s) of the BODIPY core have been prepared by Knoevenagel condensation reaction and characterized by one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR), UV-vis, fluorescence spectroscopy, high-resolution mass spectrometry as well as X-ray crystallography. The redox properties of new donor-acceptor BODIPY dyads and triads were studied by electrochemical (cyclic voltammetry (CV) and differential pulse voltammetry (DPV)) and spectroelectrochemical approaches. Formation of weakly bonded noncovalent complexes between the new pyrene-BODIPYs and nanocarbon materials (C60, C70, single-walled carbon nanotube (SWCNT), and graphene) was studied by UV-vis, steady-state fluorescent, and time-resolved transient absorption spectroscopy. UV-vis and fluorescent spectroscopy are indicative of the much stronger and selective interaction between new dyes and (6,5)-SWCNT as well as graphene compared to that of C60 and C70 fullerenes. In agreement with these data, transient absorption spectroscopy provided no evidence for any significant change in excited-state lifetime or photoinduced charge transfer between pyrene-BODIPYs and C60 or C70 fullerenes when the pyrene-BODIPY chromophores were excited into the lowest-energy singlet excited state. Density functional theory (DFT) and time-dependent DFT (TDDFT) calculations suggest that the pyrene fragments are fully conjugated into the π-system of BODIPY core, which correlates well with the experimental data.

Original language	English (US)
Pages (from-to)	360-371
Number of pages	12
Journal	Journal of Physical Chemistry B
Volume	125
Issue number	1
DOIs	https://doi.org/10.1021/acs.jpcb.0c10074
State	Published - Jan 14 2021

Bibliographical note

Funding Information:
Generous support from the Minnesota Supercomputing Institute, NSERC, CFI, University of Manitoba, NSF (CHE-1464711), WestGrid Canada, and the University of Tennessee to V.N.N. is greatly appreciated. The authors would also like to acknowledge Mathew Kaieser for his help with the initial set of transient absorption spectra.

Publisher Copyright:
© 2020 American Chemical Society.

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10.1021/acs.jpcb.0c10074

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Zatsikha, Y. V., Blesener, T. S., King, A. J., Healy, A. T., Goff, P. C., Didukh, N. O., Blank, D. A., Kovtun, Y. P., & Nemykin, V. N. (2021). Fully Conjugated Pyrene-BODIPY and Pyrene-BODIPY-Ferrocene Dyads and Triads: Synthesis, Characterization, and Selective Noncovalent Interactions with Nanocarbon Materials. Journal of Physical Chemistry B, 125(1), 360-371. https://doi.org/10.1021/acs.jpcb.0c10074

Fully Conjugated Pyrene-BODIPY and Pyrene-BODIPY-Ferrocene Dyads and Triads: Synthesis, Characterization, and Selective Noncovalent Interactions with Nanocarbon Materials. / Zatsikha, Yuriy V.; Blesener, Tanner S.; King, Alex J. et al.
In: Journal of Physical Chemistry B, Vol. 125, No. 1, 14.01.2021, p. 360-371.

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

Zatsikha, YV, Blesener, TS, King, AJ, Healy, AT, Goff, PC, Didukh, NO, Blank, DA, Kovtun, YP & Nemykin, VN 2021, 'Fully Conjugated Pyrene-BODIPY and Pyrene-BODIPY-Ferrocene Dyads and Triads: Synthesis, Characterization, and Selective Noncovalent Interactions with Nanocarbon Materials', Journal of Physical Chemistry B, vol. 125, no. 1, pp. 360-371. https://doi.org/10.1021/acs.jpcb.0c10074

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abstract = "Several pyrene-boron-dipyrromethene (BODIPY) and pyrene-BODIPY-ferrocene derivatives with a fully conjugated pyrene fragment appended to the α-position(s) of the BODIPY core have been prepared by Knoevenagel condensation reaction and characterized by one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR), UV-vis, fluorescence spectroscopy, high-resolution mass spectrometry as well as X-ray crystallography. The redox properties of new donor-acceptor BODIPY dyads and triads were studied by electrochemical (cyclic voltammetry (CV) and differential pulse voltammetry (DPV)) and spectroelectrochemical approaches. Formation of weakly bonded noncovalent complexes between the new pyrene-BODIPYs and nanocarbon materials (C60, C70, single-walled carbon nanotube (SWCNT), and graphene) was studied by UV-vis, steady-state fluorescent, and time-resolved transient absorption spectroscopy. UV-vis and fluorescent spectroscopy are indicative of the much stronger and selective interaction between new dyes and (6,5)-SWCNT as well as graphene compared to that of C60 and C70 fullerenes. In agreement with these data, transient absorption spectroscopy provided no evidence for any significant change in excited-state lifetime or photoinduced charge transfer between pyrene-BODIPYs and C60 or C70 fullerenes when the pyrene-BODIPY chromophores were excited into the lowest-energy singlet excited state. Density functional theory (DFT) and time-dependent DFT (TDDFT) calculations suggest that the pyrene fragments are fully conjugated into the π-system of BODIPY core, which correlates well with the experimental data.",

author = "Zatsikha, {Yuriy V.} and Blesener, {Tanner S.} and King, {Alex J.} and Healy, {Andrew T.} and Goff, {Philip C.} and Didukh, {Natalia O.} and Blank, {David A.} and Kovtun, {Yuriy P.} and Nemykin, {Victor N.}",

note = "Funding Information: Generous support from the Minnesota Supercomputing Institute, NSERC, CFI, University of Manitoba, NSF (CHE-1464711), WestGrid Canada, and the University of Tennessee to V.N.N. is greatly appreciated. The authors would also like to acknowledge Mathew Kaieser for his help with the initial set of transient absorption spectra. Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

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AU - Blesener, Tanner S.

AU - King, Alex J.

AU - Healy, Andrew T.

AU - Goff, Philip C.

AU - Didukh, Natalia O.

AU - Blank, David A.

AU - Kovtun, Yuriy P.

AU - Nemykin, Victor N.

N1 - Funding Information: Generous support from the Minnesota Supercomputing Institute, NSERC, CFI, University of Manitoba, NSF (CHE-1464711), WestGrid Canada, and the University of Tennessee to V.N.N. is greatly appreciated. The authors would also like to acknowledge Mathew Kaieser for his help with the initial set of transient absorption spectra. Publisher Copyright: © 2020 American Chemical Society.

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N2 - Several pyrene-boron-dipyrromethene (BODIPY) and pyrene-BODIPY-ferrocene derivatives with a fully conjugated pyrene fragment appended to the α-position(s) of the BODIPY core have been prepared by Knoevenagel condensation reaction and characterized by one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR), UV-vis, fluorescence spectroscopy, high-resolution mass spectrometry as well as X-ray crystallography. The redox properties of new donor-acceptor BODIPY dyads and triads were studied by electrochemical (cyclic voltammetry (CV) and differential pulse voltammetry (DPV)) and spectroelectrochemical approaches. Formation of weakly bonded noncovalent complexes between the new pyrene-BODIPYs and nanocarbon materials (C60, C70, single-walled carbon nanotube (SWCNT), and graphene) was studied by UV-vis, steady-state fluorescent, and time-resolved transient absorption spectroscopy. UV-vis and fluorescent spectroscopy are indicative of the much stronger and selective interaction between new dyes and (6,5)-SWCNT as well as graphene compared to that of C60 and C70 fullerenes. In agreement with these data, transient absorption spectroscopy provided no evidence for any significant change in excited-state lifetime or photoinduced charge transfer between pyrene-BODIPYs and C60 or C70 fullerenes when the pyrene-BODIPY chromophores were excited into the lowest-energy singlet excited state. Density functional theory (DFT) and time-dependent DFT (TDDFT) calculations suggest that the pyrene fragments are fully conjugated into the π-system of BODIPY core, which correlates well with the experimental data.

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Fully Conjugated Pyrene-BODIPY and Pyrene-BODIPY-Ferrocene Dyads and Triads: Synthesis, Characterization, and Selective Noncovalent Interactions with Nanocarbon Materials

Abstract

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