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Cold photo-carving of halogen-bonded co-crystals of a dye and a volatile co-former using visible light

Nature Chemistry volume 14, pages 574–581 (2022)Cite this article

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Abstract

The formation of co-crystals by the assembly of molecules with complementary molecular recognition functionalities is a popular strategy to design or improve a range of solid-state properties, including those relevant for pharmaceuticals, photo- or thermoresponsive materials and organic electronics. Here, we report halogen-bonded co-crystals of a fluorinated azobenzene derivative with a volatile component—either dioxane or pyrazine—that can be cut, carved or engraved with low-power visible light. This cold photo-carving process is enabled by the co-crystallization of a light-absorbing azo dye with a volatile component, which gives rise to materials that can be selectively disassembled with micrometre precision using low-power, non-burning laser irradiation or a commercial confocal microscope. The ability to shape co-crystals in three dimensions using laser powers of 0.5–20 mW—substantially lower than those used for metals, ceramics or polymers—is rationalized by photo-carving that targets the disruption of weak supramolecular interactions, rather than the covalent bonds or ionic structures targeted by conventional laser beam or focused ion beam machining processes.

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Fig. 1: Illustration of the CPC of a halogen-bonded co-crystal.
Fig. 2: Wavelength dependence of the machining of (trans-azo)(dioxane) co-crystals with visible light.
Fig. 3: Detailed patterns inscribed onto the surface of (trans-azo)(dioxane) co-crystals using either a laboratory laser set-up or a confocal microscope system.
Fig. 4: Comparison of the outcomes of the CPC process on the co-crystals (trans-azo)(dioxane) and irradiation of a crystal of trans-azo, based on SEM.
Fig. 5: Illustration of the CPC of (trans-azo)(pyrazine) co-crystals.

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Data availability

Crystallographic data for the structures reported in this article have been deposited at the Cambridge Crystallographic Data Centre, under deposition numbers CCDC 2068925 (for the (trans-azo)(dioxane) co-crystal), 2068926 (for the (trans-azo)(pyrazine) co-crystal) and 2068927 (for the trans-azo polymorph II). Copies of the data can be obtained free of charge via https://www.ccdc.cam.ac.uk/structures/. Source data are provided with this paper. All other data supporting the findings of this study are available within the paper and its Supplementary Information files.

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Acknowledgements

We thank 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.), RGPIN-2017-06467 (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. 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, R. D. Rogers of the University of Alabama for the use of a high-speed camera and S. Borchers for the image of the laser source used in Fig. 1d. We acknowledge the use of the Cedar supercomputer, enabled by WestGrid and Compute Canada.

Author information

Authors and Affiliations

  1. Department of Chemistry, McGill University, Montreal, Quebec, Canada

    T. H. Borchers, F. Topić, J.-C. Christopherson, O. S. Bushuyev, J. Vainauskas, H. M. Titi, T. Friščić & C. J. Barrett

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  1. T. H. Borchers
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Contributions

Experimental work was conducted by T.H.B., O.S.B., J.-C.C., F.T., J.V. and H.M.T. The experiment planning and analysis was completed jointly by T.H.B., O.S.B., J.-C.C., F.T., H.M.T., T.F. and C.J.B. The research was coordinated by T.F. and C.J.B. All the authors participated in preparing and/or editing the manuscript.

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Correspondence to T. Friščić or C. J. Barrett.

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Supplementary Information

Supplementary Information

Supplementary Figs. 1–48, Tables 1–3, discussion on polymorphism of trans-azo.

Supplementary Video 1

Photo-carving of (trans-azo)(pyrazine), performed using a 532 nm 15 mW laser.

Supplementary Video 2

Photo-carving of (trans-azo)(dioxane), performed using a 532 nm 10 mW laser.

Supplementary Video 3

Detailed photo-carving of (trans-azo)(dioxane) cocrystal independent of crystal face, performed using a 532 nm 10 mW laser.

Supplementary Video 4

Precision photo-carving of (trans-azo)(dioxane). A series of ~200 μm steps are carved through the crystal using a 532 nm 10 mW laser.

Supplementary Video 5

Slow motion video of (trans-azo)(dioxane) irradiated with a 140 ms pulse of a 10 mW 532 nm laser.

Supplementary Video 6

Slow motion photo-carving of (trans-azo)(dioxane) crystal, performed using a 532 nm 10 mW laser.

Supplementary Data 1

Cif file for (trans-azo)(dioxane).

Supplementary Data 2

Cif file for (trans-azo)(pyrazine).

Supplementary Data 3

Cif file for trans-azo II.

Source data

Source Data Fig. 2

Figure2a_Green (532 nm)LaserIrrad_raw.txt: a text file containing the data seen in Fig. 2a. for the 532 nm laser (Green dots). Figure2a_Red (785 nm)LaserIrrad_raw.txt: a text file containing the data seen in Fig. 2a. for the 785 nm laser (red dots). Figure2b_red(785 nm)Laserirrad_raw.txt: the unprocessed Raman spectrum of (trans-azo)(dioxane) appearing in waterfall plot Fig. 2b. Figure2c_green(532 nm)Laserirrad_raw.txt: the unprocessed Raman spectrum of (trans-azo)(dioxane) appearing in waterfall plot Fig. 2c.

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Borchers, T.H., Topić, F., Christopherson, JC. et al. Cold photo-carving of halogen-bonded co-crystals of a dye and a volatile co-former using visible light. Nat. Chem. 14, 574–581 (2022). https://doi.org/10.1038/s41557-022-00909-0

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