Expanding excitation wavelengths for azobenzene photoswitching into the near-infrared range <i>via</i> endothermic triplet energy transfer

Isokuortti, Jussi; Kuntze, Kim; Virkki, Matti; Ahmed, Zafar; Vuorimaa‐Laukkanen, Elina; Filatov, Mikhail A.; Turshatov, Andrey; Laaksonen, Timo; Priimägi, Arri; Durandin, Nikita

doi:10.1039/d1sc01717a

Cited by 41 publications

(74 citation statements)

References 49 publications

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“…For instance, light energy transfer technology has the potential to generate new opportunities for ''red-shifting'' MOST systems. 51 In this context, advanced triplet sensitizers promise to radically enhance efficiency as near-infrared to ultraviolet, and near-infrared to visible photon upconversion systems can use a larger part of the solar spectrum. [140][141][142] From a more general and optimistic perspective, the AI technology that is currently being developed 143 can potentially scan billions of possible molecular structures based on established DFT calculation benchmarks, 17,18,69,144 hence predicting the most optimal molecular structures to prepare.…”

Section: Discussionmentioning

confidence: 99%

“…In addition to direct chemical modification, different photophysical methods have also been explored, including the use of sensitizers [48][49][50][51] and more recently, the use of photon upconversion systems. The latter systems convert low-energy photons that otherwise cannot be absorbed by the molecules into higher-energy photons.…”

Section: Most Challenges and Solutionsmentioning

confidence: 99%

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Storing energy with molecular photoisomers

Wang

Erhart

et al. 2021

Joule

127

162

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Section: Discussionmentioning

confidence: 99%

Section: Most Challenges and Solutionsmentioning

confidence: 99%

Storing energy with molecular photoisomers

Wang

Erhart

et al. 2021

Joule

127

162

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“…5b,c), a unique feature for thermally stable azobenzenes (cis-lifetime of 81 days at 25°C, see next section). Direct photoisomerization in the opposite direction is not effective, but the back-isomerization can be accomplished with, e.g., a red-or near-infrared-activated triplet sensitizer 57 or via electron transfer [58][59][60][61] .…”

Section: Photoisomerization Efficiencymentioning

confidence: 99%

Towards low-energy-light-driven bistable photoswitches: ortho-fluoroaminoazobenzenes

Kuntze¹,

Viljakka²,

Titov³

et al. 2021

Preprint

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Thermally stable photoswitches that are driven with low-energy light are rare, yet crucial for extending the applicability of photoresponsive molecules and materials towards, e.g., living systems. Combined ortho-fluorination and -amination couples high visible-light absorptivity of o-aminoazobenzenes with the extraordinary bistability of o-fluoroazobenzenes. Herein, we report a library of easily accessible o-aminofluoroazobenzenes and establish structure–property relationships regarding spectral qualities, visible light isomerization efficiency and thermal stability of the cis-isomer with respect to the degree of o-substitution and choice of amino substituent. We rationalize the experimental results with quantum chemical calculations, revealing the nature of low-lying excited states and providing insight into thermal isomerization. The synthesized azobenzenes absorb at up to 600 nm and their thermal cis-lifetimes range from milliseconds to months. The most unique example can be driven from trans to cis with any wavelength from UV up to 595 nm, while still exhibiting a thermal cis-lifetime of 81 days.

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“…S94d). Direct photoisomerization in the opposite direction is not effective, but the back-isomerization can be accomplished with, e.g., a red-or near-infrared-activated triplet sensitizer [59] or via electron transfer [60][61][62][63].…”

Section: Photoisomerization Efficiencymentioning

confidence: 99%

Towards low-energy-light-driven bistable photoswitches: ortho-fluoroaminoazobenzenes

Kuntze

Viljakka

Titov

et al. 2021

Photochem Photobiol Sci

Self Cite

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Thermally stable photoswitches that are driven with low-energy light are rare, yet crucial for extending the applicability of photoresponsive molecules and materials towards, e.g., living systems. Combined ortho-fluorination and -amination couples high visible light absorptivity of o-aminoazobenzenes with the extraordinary bistability of o-fluoroazobenzenes. Herein, we report a library of easily accessible o-aminofluoroazobenzenes and establish structure–property relationships regarding spectral qualities, visible light isomerization efficiency and thermal stability of the cis-isomer with respect to the degree of o-substitution and choice of amino substituent. We rationalize the experimental results with quantum chemical calculations, revealing the nature of low-lying excited states and providing insight into thermal isomerization. The synthesized azobenzenes absorb at up to 600 nm and their thermal cis-lifetimes range from milliseconds to months. The most unique example can be driven from trans to cis with any wavelength from UV up to 595 nm, while still exhibiting a thermal cis-lifetime of 81 days. Graphical abstract

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Expanding excitation wavelengths for azobenzene photoswitching into the near-infrared range via endothermic triplet energy transfer

Abstract: Triplet energy transfer enables efficient Z-to-E photoswitching of azobenzenes even with near-infrared light. Ultrafast intersystem crossing of azobenzene makes the process entropy-driven and enables the use of endothermic sensitizer-azobenzene pairs.

Cited by 41 publications

References 49 publications

Storing energy with molecular photoisomers

Storing energy with molecular photoisomers

Towards low-energy-light-driven bistable photoswitches: ortho-fluoroaminoazobenzenes

Towards low-energy-light-driven bistable photoswitches: ortho-fluoroaminoazobenzenes

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