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Mechanically gated formation of donor–acceptor Stenhouse adducts enabling mechanochemical multicolour soft lithography

Overholts, Anna C. and Granados Razo, Wendy and Robb, Maxwell J. (2023) Mechanically gated formation of donor–acceptor Stenhouse adducts enabling mechanochemical multicolour soft lithography. Nature Chemistry . ISSN 1755-4330. doi:10.1038/s41557-022-01126-5. (In Press)

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Stress-sensitive molecules called mechanophores undergo productive chemical transformations in response to mechanical force. A variety of mechanochromic mechanophores, which change colour in response to stress, have been developed, but modulating the properties of the dyes generally requires the independent preparation of discrete derivatives. Here we introduce a mechanophore platform enabling mechanically gated multicolour chromogenic reactivity. The mechanophore is based on an activated furan precursor to donor–acceptor Stenhouse adducts (DASAs) masked as a hetero-Diels–Alder adduct. Mechanochemical activation of the mechanophore unveils the DASA precursor, and subsequent reaction with a secondary amine generates an intensely coloured DASA. Critically, the properties of the DASA are controlled by the amine, and thus a single mechanophore can be differentiated post-activation to produce a wide range of functionally diverse DASAs. We highlight this system by establishing the concept of mechanochemical multicolour soft lithography whereby a complex multicolour composite image is printed into a mechanochemically active elastomer through an iterative process of localized compression followed by reaction with different amines.

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Overholts, Anna C.0000-0002-0593-6903
Robb, Maxwell J.0000-0002-0528-9857
Additional Information:Financial support from Caltech is gratefully acknowledged. A.C.O. was supported by a National Science Foundation Graduate Research Fellowship (DGE-1745301) and an Institute Fellowship from Caltech. We thank M. Shahgholi for technical assistance with mass spectrometry and M. Takase for assistance with X-ray crystallography. Contributions. M.J.R. conceptualized the project and provided guidance during all stages. A.C.O. and M.J.R. designed the research. A.C.O. and W.G.R. performed the experiments. A.C.O., W.G.R. and M.J.R. analysed the data. A.C.O. and M.J.R. wrote the paper. Data availability. All data are available in the manuscript or the Supplementary Information. Experimental data and characterization data for all new compounds prepared in the course of these studies are provided in the Supplementary Information of this paper. The X-ray crystallographic coordinates for compound (±)-3 have been deposited at the Cambridge Crystallographic Data Center (CCDC) with deposition no. 2163133. These data can be obtained free of charge from the CCDC via Source data are provided with this paper. Competing interests. A.C.O. and M.J.R. are inventors on a US provisional patent application submitted by California Institute of Technology (CIT 8808-P) covering the chemistry and lithographic process disclosed herein.
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NSF Graduate Research FellowshipDGE-1745301
Record Number:CaltechAUTHORS:20230215-568360000.2
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ID Code:119289
Deposited By: George Porter
Deposited On:15 Feb 2023 18:19
Last Modified:24 Feb 2023 18:12

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