Improve the Crosslinking Reactivity of Nitrile: Design of Nitrile‐Functionalized Pyrazine and its Hydrogen Bond‐Assisted Nucleophilic Enhancement Study

Author:

He Xian1ORCID,Wu Hao1,Chen Menghao1,Lv Jiangbo1,Xiao Hang1,Salas Maria Nieves López2,Wu Baile3,Liu Pengqing1,Zeng Ke1,Yang Gang1ORCID

Affiliation:

1. College of Polymer Science and Engineering, State Key Laboratory of Polymer Materials Engineering Sichuan University Chengdu 610065 P. R. China

2. Department Sustainable Materials Chemistry Department of Chemistry Paderborn University Warburger Straße 100 D‐33098 Paderborn Germany

3. School of Sustainable Engineering and the Built Environment, Ira A. Fulton Schools of Engineering Arizona State University Tempe AZ 85287 USA

Abstract

AbstractIn this study, molecular engineering and biomimetic principles are utilized to prepare highly effective nitrile‐functionalized pyrazine crosslinking units by exploiting pyrazine's unique nucleophilic strengthening mechanism and proton bonding ability. The curing behaviors of pyrazine‐2,3‐dicarbonitrile and phthalonitrile are investigated through model curing systems and molecular simulation. The results indicate that pyrazine‐2,3‐dicarbonitrile exhibits higher reactivity than phthalonitrile, promoted by amine. The cured products of pyrazine‐2,3‐dicarbonitrile predominantly comprise thermally stable azaisoindoline and azaphthalocyanine. This novel type of highly effective crosslinking unit, and the comprehended mechanism of action of pyrazine at the molecular level, significantly expand the application of pyrazine in materials science.

Publisher

Wiley

Subject

Materials Chemistry,Polymers and Plastics,Organic Chemistry

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