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Panchromatic Light-Absorbing [70]Fullerene-Perylene-BODIPY Triad with Cascade of Energy Transfer as an Efficient Singlet Oxygen Sensitizer.

ABSTRACT: A panchromatic light-absorbing [70]fullerene-perylene-BODIPY triad (C₇₀-P-B) was synthesized and applied as a heavy atom-free organic triplet photosensitizer for photooxidation. The photophysical processes were comprehensively investigated by the methods of steady-state spectroscopy, time-resolved spectroscopy, as well as theoretical calculations. C₇₀-P-B shows a strong absorption ability from 300-620 nm. Efficient cascading intramolecular singlet-singlet energy transfer in C₇₀-P-B was confirmed by the luminescence study. The backward triplet excited state energy transfer from C₇₀ moiety to perylene then occurs to populate ³perylene*. Thus, the triplet excited states of C₇₀-P-B are distributed on both C₇₀ and perylene moiety with lifetimes of 23 ± 1 μs and 175 ± 17 μs, respectively. C₇₀-P-B exhibits excellent photooxidation capacity, and its yield of singlet oxygen reaches 0.82. The photooxidation rate constant of C₇₀-P-B is 3.70 times that of C₇₀-Boc and 1.58 times that of MB, respectively. The results in this paper are useful for designing efficient heavy atom-free organic triplet photosensitizers for practical application in photovoltaics, photodynamic therapy, etc.

SUBMITTER: Dou L

PROVIDER: S-EPMC10144093 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature

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Panchromatic Light-Absorbing [70]Fullerene-Perylene-BODIPY Triad with Cascade of Energy Transfer as an Efficient Singlet Oxygen Sensitizer.

Dou Lifeng L Li Yuanming Y Dong Lei L Zhang Shuao S Wu Yuanqi Y Gong Yu Y Yang Wei W Lu Hongdian H Zhu Sane S Zhou Xiaoguo X

Molecules (Basel, Switzerland) 20230417 8

A panchromatic light-absorbing [70]fullerene-perylene-BODIPY triad (C70-P-B) was synthesized and applied as a heavy atom-free organic triplet photosensitizer for photooxidation. The photophysical processes were comprehensively investigated by the methods of steady-state spectroscopy, time-resolved spectroscopy, as well as theoretical calculations. C70-P-B shows a strong absorption ability from 300-620 nm. Efficient cascading intramolecular singlet-singlet ener ...[more]

PMID: 37110773

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Project description:Photoreduction of fullerene and the consequent stabilisation of a charge-separated state in a donor-acceptor assembly have been achieved, overcoming the common problem of a fullerene-based triplet state being an energy sink that prevents charge-separation. A route to incorporate a C60-fullerene electron acceptor moiety into a catecholate-Pt(ii)-diimine photoactive dyad, which contains an unusually strong electron donor, 3,5-di-tert-butylcatecholate, has been developed. The synthetic methodology is based on the formation of the aldehyde functionalised bipyridine-Pt(ii)-3,5-di-tert-butylcatechol dyad which is then added to the fullerene cage via a Prato cycloaddition reaction. The resultant product is the first example of a fullerene-diimine-Pt-catecholate donor-acceptor triad, C60bpy-Pt-cat. The triad exhibits an intense solvatochromic absorption band in the visible region due to catechol-to-diimine charge-transfer, which, together with fullerene-based transitions, provides efficient and tuneable light harvesting of the majority of the UV/visible spectral range. Cyclic voltammetry, EPR and UV/vis/IR spectroelectrochemistry reveal redox behaviour with a wealth of reversible reduction and oxidation processes forming multiply charged species and storing multiple redox equivalents. Ultrafast transient absorption and time resolved infrared spectroscopy, supported by molecular modelling, reveal the formation of a charge-separated state [C60˙-bpy-Pt-cat˙+] with a lifetime of ∼890 ps. The formation of cat˙+ in the excited state is evidenced directly by characteristic absorption bands in the 400-500 nm region, while the formation of C60˙- was confirmed directly by time-resolved infrared spectroscopy, TRIR. An IR-spectroelectrochemical study of the mono-reduced building block (C60-bpy)PtCl2, revealed a characteristic C60˙- vibrational feature at 1530 cm-1, which was also detected in the TRIR spectra. This combination of experiments offers the first direct IR-identification of C60˙- species in solution, and paves the way towards the application of transient infrared spectroscopy to the study of light-induced charge-separation in C60-containing assemblies, as well as fullerene films and fullerene/polymer blends in various OPV devices. Identification of the unique vibrational signature of a C60-anion provides a new way to follow photoinduced processes in fullerene-containing assemblies by means of time-resolved vibrational spectroscopy, as demonstrated for the fullerene-transition metal chromophore assembly with the lowest energy charge-separated excited state.

Dataset Information

Panchromatic Light-Absorbing [70]Fullerene-Perylene-BODIPY Triad with Cascade of Energy Transfer as an Efficient Singlet Oxygen Sensitizer.

Publications

Panchromatic Light-Absorbing [70]Fullerene-Perylene-BODIPY Triad with Cascade of Energy Transfer as an Efficient Singlet Oxygen Sensitizer.

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