Facile Mechanochemical Preparation of Polyamide-derivatives via Solid-state Benzoxazine-isocyanide Chemistry
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ARTICLE
POLYMER SCIENCE
https://doi.org/10.1007/s10118-021-2510-6 Chinese J. Polym. Sci.
Facile Mechanochemical Preparation of Polyamide-derivatives via Solid-state Benzoxazine-isocyanide Chemistry Xu Sun, Wei Shi*, Xin-Yu Zhou, and Sheng Ding Oil & Gas Field Applied Chemistry Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu 610500, China
Electronic Supplementary Information Abstract With the exploration of novel sustainable protocol for functional polyamides’ (PAs) construction as the starting point, herein, the small molecular model compound (M1-ssBIC) was prepared firstly by manual grinding of monofunctional benzoxazine (1a) and isocyanide (1b) via solid-state benzoxazine-isocyanide chemistry (ssBIC) to evaluate the feasibility of ssBIC. Linear PAs (P1-series polymers) were subsequently synthesized from biunctional benzoxazine (2a) and isocyanide (2b), and the influence of the loading of catalyst (octylphosphonic acid) (OPA) on the polymerization was investigated. Afterwards, two kinds of cross-linked PAs were successfully constructed via ssBIC by using trifunctional benzoxazine (3a) and cross-linked polybenzoxazine (4a) as reaction substrates, respectively, thus verifying the adaptability of ssBIC. Structural characterization indicates that amide, phenolic hydroxyl and tertiary amine substructures, with metal-complexing capability, have been successfully integrated into the obtained PAs. A type of representative PA/silver composite (P3-AgNPs) was prepared subsequently via in situ reduction treatment, and its application as recyclable reduction catalyst for organic pollutant p-nitrophenol (4-NP) was preliminarily investigated here to provide the example for possible downstream application of ssBIC. We think that this current work could provide a new pathway for the construction of functional PAs through facile and sustainable ssBIC protocol. Keywords Mechanochemistry; Solid-state synthesis; Benzoxazine; Isocyanide; Polyamide Citation: Sun, X.; Shi, W.; Zhou, X. Y.; Ding, S. Facile mechanochemical preparation of polyamide-derivatives via solid-state benzoxazine-isocyanide chemistry. Chinese J. Polym. Sci. https://doi.org/10.1007/s10118-021-2510-6
INTRODUCTION Compared with the liquid-state reaction, the solid-state reaction (SSR) (usually categorised as typical mechanochemical reaction (MCR)) shows the advantages of being independent of the solubility of reaction substrates/intermediates, no need to use solvents, easy scaling up and high reaction speed, etc. Therefore, SSR has attracted intensive attention in recent years to act as a sustainable synthetic approach.[1−4] Up to now, SSR has been successfully utilized in reactions of Scholl,[5] Sonogashira,[6] Michael,[7] Click,[8] and Ritter,[9] etc. Despite the high efficiency of SSR in the preparation of small molecular compounds, there are much fewer reports regarding the preparation of polymers by SSR. In general, mechanical force has been considered as the destruction p
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