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A rational design strategy of radical-type mechanophores with thermal tolerance.

ABSTRACT: Radical-type mechanophores (RMs) are attractive molecules that undergo homolytic scission of their central C-C bond to afford radical species upon exposure to heat or mechanical stimuli. However, the lack of a rational design concept limits the development of RMs with pre-determined properties. Herein, we report a rational design strategy of RMs with high thermal tolerance while maintaining mechanoresponsiveness. A combined experimental and theoretical analysis revealed that the high thermal tolerance of these RMs is related to the radical-stabilization energy (RSE) as well as the Hammett and modified Swain-Lupton constants at the para-position (σ_p). The trend of the RSE values is in good agreement with the experimentally evaluated thermal tolerance of a series of mechanoresponsive RMs based on the bisarylcyanoacetate motif. Furthermore, the singly occupied molecular orbital (SOMO) levels clearly exhibit a negative correlation with σ_p within a series of RMs that are based on the same skeleton, paving the way toward the development of RMs that can be handled under ambient conditions without peroxidation.

SUBMITTER: Lu Y

PROVIDER: S-EPMC10445462 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature

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A rational design strategy of radical-type mechanophores with thermal tolerance.

Lu Yi Y Sugita Hajime H Mikami Koichiro K Aoki Daisuke D Otsuka Hideyuki H

Chemical science 20230803 33

Radical-type mechanophores (RMs) are attractive molecules that undergo homolytic scission of their central C-C bond to afford radical species upon exposure to heat or mechanical stimuli. However, the lack of a rational design concept limits the development of RMs with pre-determined properties. Herein, we report a rational design strategy of RMs with high thermal tolerance while maintaining mechanoresponsiveness. A combined experimental and theoretical analysis revealed that the high thermal tol ...[more]

PMID: 37621432

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Dataset Information

A rational design strategy of radical-type mechanophores with thermal tolerance.

Publications

A rational design strategy of radical-type mechanophores with thermal tolerance.

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