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二氨基马来腈的溶剂热聚合揭示了用于生产基于C=N聚合物的最佳绿色溶剂。

Solvothermal Polymerization of Diaminomaleonitrile Reveals Optimal Green Solvents for the Production of C=N-Based Polymers.

作者信息

López-García Antonio, Manjavacas Marina, de la Fuente José L, Ruiz-Bermejo Marta

机构信息

Dpto. Evolución Molecular, Centro de Astrobiología (CAB), CSIC-INTA, Ctra. Torrejón-Ajalvir, km 4, Torrejón de Ardoz, Madrid 28850, Spain.

Centro de Biotecnología y Genómica de Plantas UPM-INIA Parque Científico yTecnológico de la UPM Campus de Montegancedo, Madrid 28223, Spain.

出版信息

ACS Omega. 2024 Sep 24;9(40):41867-41883. doi: 10.1021/acsomega.4c06421. eCollection 2024 Oct 8.

DOI:10.1021/acsomega.4c06421
PMID:39398125
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11465270/
Abstract

Solvothermal polymerization (STP) of diaminomaleonitrile (DAMN) was evaluated using a wide variety of solvents and in the temperature range from 80 to 170 °C. The highest yields, almost quantitative, were achieved with protic -alcohols such as -pentanol or -hexanol at 130 and 150 °C, respectively. The kinetic behavior was studied by gravimetry and the DAMN consumption was monitored by UV-vis spectroscopy and HPLC. GC-MS identified byproducts of the DAMN hydrolysis and oxidation reactions, which were significantly reduced when -pentanol or -hexanol were used with respect to hydrothermal conditions. This led to an exploration of compositional changes and microstructural variations by FTIR and NMR spectroscopy and simultaneous thermal analysis. -Hexanol appears to be an ideal eco-friendly solvent for the DAMN self-STP. The results presented here are not only of interest for the design of polymeric materials based on C=N structures but also show remarkable implications for prebiotic chemistry.

摘要

使用多种溶剂并在80至170°C的温度范围内评估了二氨基马来腈（DAMN）的溶剂热聚合（STP）。分别在130°C和150°C下，使用质子醇如戊醇或己醇可实现几乎定量的最高产率。通过重量法研究了动力学行为，并通过紫外可见光谱和高效液相色谱监测了DAMN的消耗情况。气相色谱 - 质谱法鉴定了DAMN水解和氧化反应的副产物，与水热条件相比，当使用戊醇或己醇时，这些副产物显著减少。这促使通过傅里叶变换红外光谱（FTIR）、核磁共振光谱（NMR）和同步热分析来探索组成变化和微观结构变化。己醇似乎是DAMN自溶剂热聚合的理想环保溶剂。此处呈现的结果不仅对基于C=N结构的聚合物材料设计具有重要意义，而且对益生元化学也具有显著影响。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d19a/11465270/048d7ecbeffe/ao4c06421_0012.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d19a/11465270/048d7ecbeffe/ao4c06421_0012.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d19a/11465270/405bc6f8646e/ao4c06421_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d19a/11465270/bc436d5446cb/ao4c06421_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d19a/11465270/253309761478/ao4c06421_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d19a/11465270/10bc6caf1b87/ao4c06421_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d19a/11465270/d3b53ce7efb8/ao4c06421_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d19a/11465270/ce59eb6dd8da/ao4c06421_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d19a/11465270/d0e5cee2e549/ao4c06421_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d19a/11465270/29d6419c7832/ao4c06421_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d19a/11465270/048d7ecbeffe/ao4c06421_0012.jpg

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本文引用的文献

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Impact of M Dwarfs Ultraviolet Radiation on Prebiotic Chemistry: The Case of Adenine.M 矮星紫外线辐射对前生物化学的影响：以腺嘌呤为例。
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