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

Liang, Yi; Sugita, Hajime; Mikami, K.; Aoki, Daisuke; Otsuka, Hideyuki

doi:10.1039/d3sc02991c

Chem. Sci.

2023

DOI: 10.1039/d3sc02991c

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

Yi Liang

Hajime Sugita

K. Mikami

et al.

Abstract: Radical-type mechanophores (RMs) are attractive materials 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...

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Cited by 3 publications

References 73 publications

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Visible Light instead of Transition Metal: Electron Donor Acceptor Complex Enabled Cross‐Coupling of Aryl Halides with Active Methylene Compounds

Volkov,

Bugaenko,

Karchava

2023

Adv Synth Catal

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An arylation of anions of active methylene compounds with aryl halides provides an access to synthetically versatile α‐arylated 1,3‐diketones, β‐keto esters, β‐keto nitriles, β‐cyano esters, etc. Previously, these C−C cross‐coupling reactions have been accomplished only using transition metal‐based catalysts. Herein, we demonstrate that these arylations can be successfully realized under catalyst‐free conditions employing the electron donor‐acceptor (EDA) complex photoactivation strategy. The protocol was further optimized for a semi‐one pot synthesis of indole derivatives via an intramolecular C−C coupling.

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Visible Light instead of Transition Metal: Electron Donor Acceptor Complex Enabled Cross‐Coupling of Aryl Halides with Active Methylene Compounds

Volkov,

Bugaenko,

Karchava

2023

Adv Synth Catal

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show abstract

Progress toward sustainable polymer technologies with ball-mill grinding

Rizzo,

Peterson

2024

Progress in Polymer Science

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Mechanochromic polymers based on radical-type dynamic covalent chemistry

Yamamoto,

Takahashi,

Otsuka

2023

Bulletin of the Chemical Society of Japan

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Polymer mechanochemistry has emerged as a field of considerable interest both from an academic and industrial perspective. Mechanochromic polymers that show optical change in response to mechanical stimuli can be used to visualize the mechanical force applied to the materials, which provides a wide range of information from the nano- to the macroscale, and also enables damage detection to prevent critical failure of the materials. We have explored a wide variety of radical-type dynamic covalent chemistry in the field of polymer reactions and revealed its great potential in developing mechanochromic materials. This account describes our recent efforts in the precise design of mechanochromic polymers based on radical-type dynamic covalent chemistry to impart polymeric materials with bespoke chromic properties, and discusses their characteristics derived from the radical chemistry as well as potential applications.

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

Abstract: Radical-type mechanophores (RMs) are attractive materials 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...

Cited by 3 publications

References 73 publications

Visible Light instead of Transition Metal: Electron Donor Acceptor Complex Enabled Cross‐Coupling of Aryl Halides with Active Methylene Compounds

Visible Light instead of Transition Metal: Electron Donor Acceptor Complex Enabled Cross‐Coupling of Aryl Halides with Active Methylene Compounds

Progress toward sustainable polymer technologies with ball-mill grinding

Mechanochromic polymers based on radical-type dynamic covalent chemistry

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