基于多羟基柱[5]芳烃的酚醛多孔聚合物合成及CO2催化转化

doi:10.6023/cjoc202212034

有机化学 ›› 2023, Vol. 43 ›› Issue (8): 2808-2814.DOI: 10.6023/cjoc202212034 上一篇下一篇

研究论文

基于多羟基柱[5]芳烃的酚醛多孔聚合物合成及CO₂催化转化

刘露^a, 张曙光^a, 胡仁威^a, 赵晓晓^a, 崔京南^a, 贡卫涛^a^,^b^,^*()

a 大连理工大学化工学院精细化工国家重点实验室辽宁大连 116024
b 大连理工大学辽宁省硼镁特种功能材料制备及应用技术工程实验室辽宁大连 116024

收稿日期:2022-12-28 修回日期:2023-02-02 发布日期:2023-04-26
基金资助:
辽宁省自然科学基金(2019-MS-046)

Synthesis and Properties of Phenolic Resin Polymers Based on Pillar[5]arene

Lu Liu^a, Shuguang Zhang^a, Renwei Hu^a, Xiaoxiao Zhao^a, Jingnan Cui^a, Weitao Gong^a^,^b()

a State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, Liaoning 116024
b Engineering Laboratory of Boric and Magnesia Functional Material Preparative and Applied Technology of Liaoning Province, Dalian University of Technology, Dalian, Liaoning 116024

Received:2022-12-28 Revised:2023-02-02 Published:2023-04-26
Contact: *E-mail: wtgong@dlut.edu.cn
Supported by:
The Natural Science Foundation of Liaoning Province(2019-MS-046)

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摘要/Abstract

分别以双羟基、全羟基官能化的柱[5]芳烃大环为聚合单体, 1,4-二(4-醛基苯基)苯为交联剂, 通过酚醛缩合反应一步聚合得到了两种新型的酚醛多孔有机聚合物(PRP-1、PRP-2). 通过固体核磁碳谱(¹³C CP/MAS NMR)、傅里叶变换红外光谱(FT-IR)、X射线粉末衍射(PXRD)、扫描电子显微镜(SEM)、氮气和二氧化碳吸脱附和热重分析(TG)对聚合物材料进行了表征. 结果表明柱[5]芳烃大环上的羟基数量对聚合物结构具有显著影响, 具有更多羟基数量的PRP-2的比表面积是PRP-1的10倍以上. 两个聚合物均可用于非均相催化二氧化碳(CO₂)和环氧化物的环加成反应, 而且PRP-2展现出更高的转化率.

关键词: 有机多孔聚合物, 柱[5]芳烃, 酚醛聚合物, 二氧化碳转化

Two new phenolic resin porous organic polymers PRP-1, PRP-2 were obtained by one-step polymerization of phenolic resin reaction using functionalized pillar[n]arene and 1,4-bis(4-formylphenyl)benzene as polymerization monomers. The pore characters of PRP-1 and PRP-2 were evaluated by solid-state nuclear magnetic carbon spectroscopy (¹³C CP/MAS NMR), fourier transform infrared spectroscopy (FT-IR), X-ray powder diffraction (PXRD), scanning electron microscopy (SEM), nitrogen and carbon dioxide adsorption and desorption, and thermogravimetric analysis (TG). The results showed that mutilid-hydroxyl groups on the aromatic macrocycles of pillar[5]arene significantly affect the polymer structure, and the specific surface area of PRP-2 with a higher number of hydroxyl groups is more than 10 times higher than that of PRP-1. Polymers PRP-1 and PRP-2 can be used for non-homogeneous catalytic carbon dioxide (CO₂) conversion, and PRP-2 exhibits higher conversion. This work shows that the functionalized pillar[n]arene has a potential application in organic porous polymers.

Key words: organic porous polymer, pillar[5]arene, phenolic resin-type polymer, CO₂ conversion

引用此文

刘露, 张曙光, 胡仁威, 赵晓晓, 崔京南, 贡卫涛. 基于多羟基柱[5]芳烃的酚醛多孔聚合物合成及CO₂催化转化[J]. 有机化学, 2023, 43(8): 2808-2814.

Lu Liu, Shuguang Zhang, Renwei Hu, Xiaoxiao Zhao, Jingnan Cui, Weitao Gong. Synthesis and Properties of Phenolic Resin Polymers Based on Pillar[5]arene[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2808-2814.

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图/表 6

图式1. PRP-1、PRP-2的合成示意图

Scheme 1. Schematic of the preparation of PRP-1 and PRP-2

图1. (a) PRT-1和(b) PRT-2的FT-IR谱; (c) PRT-1和(d) PRT-2的固体核磁谱图

Figure 1. FT-IR spectra of PRT-1 (a) and PRT-2 (b), and 13C CP/MAS NMR spectra of PRT-1 (c) and PRT-2 (d)

图2. PRT-1 (a)和PRT-2 (b)的扫描电镜照片

Figure 2. SEM micrographs of PRT-1 (a) and PRT-2 (b)

图3. 77 K下PRT-1、PRT-2的氮吸附与脱附等温线(a)以及孔径分布图(b); (c) PRT-1和PRT-2在273 K的CO2吸附与脱附等温线; (d) PRT-1和PRT-2在298 K的CO2吸附与脱附等温线

Figure 3. Nitrogen sorption isotherms of PRT-1 and PRT-2 at 77 K; (b) pore size distribution of PRT-1 and PRT-2; (c) CO2 adsorption and desorption isotherms of PRT-1 and PRT-2 at 273 K; (d) CO2 adsorption and desorption isotherms of PRT-1 and PRT-2 at 298 K

Entry	Cat.	T/℃	p/MPa	t/h	Yield/%
1	—	25	1	24	1.31
2	PRT-2	60	1	24	55.4
3	PRT-2	80	1	36	89.4
4	PRT-1	80	1	36	78.5

表1. PRT-1和PRT-2催化CO2与环氧丙烷的环加成反应a

Table 1. Cyclo-addition of CO2 with propylene oxide catalyzed by PRT-1 and PRT-2

Entry	Epoxide	Cyclic carbouate	Yield/%
1			89.4
2			99.0
3			87.4
4			99.8
5			59.8

表2. PRT-2催化CO2与的环加成反应底物拓展a

Table 2. Substrate scope of the cyclo-addition of CO2 catalyzed by PRT-2

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基于多羟基柱[5]芳烃的酚醛多孔聚合物合成及CO₂催化转化

Synthesis and Properties of Phenolic Resin Polymers Based on Pillar[5]arene

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