Three-in-One: Dye-Volatile Cocrystals Exhibiting Intensity-Dependent Photochromic, Photomechanical, and Photocarving Response

Tristan H Borchers; Filip Topić; Mihails Arhangelskis; Jogirdas Vainauskas; Hatem M Titi; Oleksandr S Bushuyev; Christopher J Barrett; Tomislav Friščić

doi:10.1021/jacs.3c07060

Three-in-One: Dye-Volatile Cocrystals Exhibiting Intensity-Dependent Photochromic, Photomechanical, and Photocarving Response

Tristan H Borchers, Filip Topić, Mihails Arhangelskis, Jogirdas Vainauskas, Hatem M Titi, Oleksandr S Bushuyev, Christopher J Barrett^*, Tomislav Friščić^*

^*Corresponding author for this work

Chemistry

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Abstract

Cocrystallization of a cis-azobenzene dye with volatile molecules, such as pyrazine and dioxane, leads to materials that exhibit at least three different light-intensity-dependent responses upon irradiation with low-power visible light. The halogen-bond-driven assembly of the dye cis-(p-iodoperfluorophenyl)azobenzene with volatile halogen bond acceptors produces cocrystals whose light-induced behavior varies significantly depending on the intensity of the light applied. Low-intensity (<1 mW·cm-2) light irradiation leads to a color change associated with low levels of cis → trans isomerization. Irradiation at higher intensities (150 mW·mm-2) produces photomechanical bending, caused by more extensive isomerization of the dye. At still higher irradiation intensities (2.25 W·mm-2) the cocrystals undergo cold photocarving; i.e., they can be cut and written on with micrometer precision using laser light without a major thermal effect. Real-time Raman spectroscopy shows that this novel photochemical behavior differs from what would be expected from thermal energy input alone. Overall, this work introduces a rational blueprint, based on supramolecular chemistry in the solid state, for new types of crystalline light-responsive materials, which not only respond to being exposed to light but also change their response based on the light intensity.

Original language	English
Pages (from-to)	24636–24647
Journal	Journal of the American Chemical Society
Volume	145
Issue number	45
Early online date	4 Nov 2023
DOIs	https://doi.org/10.1021/jacs.3c07060
Publication status	Published - 15 Nov 2023

Bibliographical note

Acknowledgments
We thank the University of Birmingham and the Leverhulme International Professorship (T.F., T.H.B., J.V.), the Natural Sciences and Engineering Research Council (NSERC) Canada for their financial support of this work through Discovery Grants RGPIN-2019-05661 (C.J.B.) and RGPIN-2017-06467 (T.F.), NSERC John C. Polanyi Award (Grant JCP 562908-2022) (T.F.), and Discovery Accelerator Award RGPAS 507837-17 (T.F.), as well as the Government of Canada for a Tier-1 Canada Research Chair (T.F.) and Vanier Graduate (O.S.B.) and Banting Postdoctoral (F.T.) Fellowships. M.A. thanks National Science Center (NCN) for the financial support via Polish National Science Center (NCN) OPUS Grant 2020/37/B/ST5/02638. The funders had no role in the study design, data collection and analysis, decision to publish, or preparation of the manuscript. We thank M. J. Harrington of McGill Chemistry for use of the confocal Raman microscope, and R. D. Rogers of the University of Alabama for the use of a high-speed camera. We acknowledge the use of the Cedar supercomputer, enabled by WestGrid and Compute Canada.

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@article{d1e9beca53b3459da86b0d543deba36a,

title = "Three-in-One: Dye-Volatile Cocrystals Exhibiting Intensity-Dependent Photochromic, Photomechanical, and Photocarving Response",

abstract = "Cocrystallization of a cis-azobenzene dye with volatile molecules, such as pyrazine and dioxane, leads to materials that exhibit at least three different light-intensity-dependent responses upon irradiation with low-power visible light. The halogen-bond-driven assembly of the dye cis-(p-iodoperfluorophenyl)azobenzene with volatile halogen bond acceptors produces cocrystals whose light-induced behavior varies significantly depending on the intensity of the light applied. Low-intensity (<1 mW·cm-2) light irradiation leads to a color change associated with low levels of cis → trans isomerization. Irradiation at higher intensities (150 mW·mm-2) produces photomechanical bending, caused by more extensive isomerization of the dye. At still higher irradiation intensities (2.25 W·mm-2) the cocrystals undergo cold photocarving; i.e., they can be cut and written on with micrometer precision using laser light without a major thermal effect. Real-time Raman spectroscopy shows that this novel photochemical behavior differs from what would be expected from thermal energy input alone. Overall, this work introduces a rational blueprint, based on supramolecular chemistry in the solid state, for new types of crystalline light-responsive materials, which not only respond to being exposed to light but also change their response based on the light intensity.",

author = "Borchers, {Tristan H} and Filip Topi{\'c} and Mihails Arhangelskis and Jogirdas Vainauskas and Titi, {Hatem M} and Bushuyev, {Oleksandr S} and Barrett, {Christopher J} and Tomislav Fri{\v s}{\v c}i{\'c}",

note = "Acknowledgments We thank the University of Birmingham and the Leverhulme International Professorship (T.F., T.H.B., J.V.), the Natural Sciences and Engineering Research Council (NSERC) Canada for their financial support of this work through Discovery Grants RGPIN-2019-05661 (C.J.B.) and RGPIN-2017-06467 (T.F.), NSERC John C. Polanyi Award (Grant JCP 562908-2022) (T.F.), and Discovery Accelerator Award RGPAS 507837-17 (T.F.), as well as the Government of Canada for a Tier-1 Canada Research Chair (T.F.) and Vanier Graduate (O.S.B.) and Banting Postdoctoral (F.T.) Fellowships. M.A. thanks National Science Center (NCN) for the financial support via Polish National Science Center (NCN) OPUS Grant 2020/37/B/ST5/02638. The funders had no role in the study design, data collection and analysis, decision to publish, or preparation of the manuscript. We thank M. J. Harrington of McGill Chemistry for use of the confocal Raman microscope, and R. D. Rogers of the University of Alabama for the use of a high-speed camera. We acknowledge the use of the Cedar supercomputer, enabled by WestGrid and Compute Canada.",

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doi = "10.1021/jacs.3c07060",

language = "English",

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T2 - Dye-Volatile Cocrystals Exhibiting Intensity-Dependent Photochromic, Photomechanical, and Photocarving Response

AU - Borchers, Tristan H

AU - Topić, Filip

AU - Arhangelskis, Mihails

AU - Vainauskas, Jogirdas

AU - Titi, Hatem M

AU - Bushuyev, Oleksandr S

AU - Barrett, Christopher J

AU - Friščić, Tomislav

N1 - Acknowledgments We thank the University of Birmingham and the Leverhulme International Professorship (T.F., T.H.B., J.V.), the Natural Sciences and Engineering Research Council (NSERC) Canada for their financial support of this work through Discovery Grants RGPIN-2019-05661 (C.J.B.) and RGPIN-2017-06467 (T.F.), NSERC John C. Polanyi Award (Grant JCP 562908-2022) (T.F.), and Discovery Accelerator Award RGPAS 507837-17 (T.F.), as well as the Government of Canada for a Tier-1 Canada Research Chair (T.F.) and Vanier Graduate (O.S.B.) and Banting Postdoctoral (F.T.) Fellowships. M.A. thanks National Science Center (NCN) for the financial support via Polish National Science Center (NCN) OPUS Grant 2020/37/B/ST5/02638. The funders had no role in the study design, data collection and analysis, decision to publish, or preparation of the manuscript. We thank M. J. Harrington of McGill Chemistry for use of the confocal Raman microscope, and R. D. Rogers of the University of Alabama for the use of a high-speed camera. We acknowledge the use of the Cedar supercomputer, enabled by WestGrid and Compute Canada.

PY - 2023/11/15

Y1 - 2023/11/15

N2 - Cocrystallization of a cis-azobenzene dye with volatile molecules, such as pyrazine and dioxane, leads to materials that exhibit at least three different light-intensity-dependent responses upon irradiation with low-power visible light. The halogen-bond-driven assembly of the dye cis-(p-iodoperfluorophenyl)azobenzene with volatile halogen bond acceptors produces cocrystals whose light-induced behavior varies significantly depending on the intensity of the light applied. Low-intensity (<1 mW·cm-2) light irradiation leads to a color change associated with low levels of cis → trans isomerization. Irradiation at higher intensities (150 mW·mm-2) produces photomechanical bending, caused by more extensive isomerization of the dye. At still higher irradiation intensities (2.25 W·mm-2) the cocrystals undergo cold photocarving; i.e., they can be cut and written on with micrometer precision using laser light without a major thermal effect. Real-time Raman spectroscopy shows that this novel photochemical behavior differs from what would be expected from thermal energy input alone. Overall, this work introduces a rational blueprint, based on supramolecular chemistry in the solid state, for new types of crystalline light-responsive materials, which not only respond to being exposed to light but also change their response based on the light intensity.

AB - Cocrystallization of a cis-azobenzene dye with volatile molecules, such as pyrazine and dioxane, leads to materials that exhibit at least three different light-intensity-dependent responses upon irradiation with low-power visible light. The halogen-bond-driven assembly of the dye cis-(p-iodoperfluorophenyl)azobenzene with volatile halogen bond acceptors produces cocrystals whose light-induced behavior varies significantly depending on the intensity of the light applied. Low-intensity (<1 mW·cm-2) light irradiation leads to a color change associated with low levels of cis → trans isomerization. Irradiation at higher intensities (150 mW·mm-2) produces photomechanical bending, caused by more extensive isomerization of the dye. At still higher irradiation intensities (2.25 W·mm-2) the cocrystals undergo cold photocarving; i.e., they can be cut and written on with micrometer precision using laser light without a major thermal effect. Real-time Raman spectroscopy shows that this novel photochemical behavior differs from what would be expected from thermal energy input alone. Overall, this work introduces a rational blueprint, based on supramolecular chemistry in the solid state, for new types of crystalline light-responsive materials, which not only respond to being exposed to light but also change their response based on the light intensity.

U2 - 10.1021/jacs.3c07060

DO - 10.1021/jacs.3c07060

M3 - Article

C2 - 37924293

SN - 0002-7863

VL - 145

SP - 24636

EP - 24647

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 45

ER -

Three-in-One: Dye-Volatile Cocrystals Exhibiting Intensity-Dependent Photochromic, Photomechanical, and Photocarving Response

Abstract

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