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

doi:10.6023/cjoc202212034

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (8): 2808-2814.DOI: 10.6023/cjoc202212034 Previous Articles Next Articles

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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Abstract

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

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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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Fig. & Tab. 6

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

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)

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

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

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

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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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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Supporting Info.

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Abstract

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References 41

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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