Advances in benzimidazole-linked polymer adsorbents and membranes

doi:10.11949/0438-1157.20221088

Abstract

Abstract:

Benzimidazole-linked polymers have excellent chemical stability, thermal stability, high porosity, high specific surface area, dielectric properties and good mechanical properties by virtue of the strong bonds in their chains, strong interactions among their chains and their versatile functional groups, and thus they were used as materials for efficient separation. In this review, the types and properties of benzimidazole-linked polymers are discussed. Applications, such as adsorbents and membranes separation are extensively reviewed. Finally, the brief summary and tentative perspectives of benzimidazole-linked polymers are presented.

Key words: benzimidazole-linked polymers, separation, adsorbents, membranes

摘要：

强的链内、链间作用力和丰富的官能团赋予苯并咪唑连接聚合物优异的化学稳定性、热稳定性、高孔隙率、高比表面积、介电性以及良好的力学性能，因此被用作高效分离材料。本文讨论了苯并咪唑连接聚合物的种类及性能，综述了其在吸附剂和膜分离领域的应用，总结了研究现状，并对未来发展进行了展望。

关键词: 苯并咪唑连接聚合物, 分离, 吸附剂, 膜

CLC Number:

TQ 028.8

Min LI, Xueru YAN, Xinlei LIU. Advances in benzimidazole-linked polymer adsorbents and membranes[J]. CIESC Journal, 2023, 74(2): 599-616.

李敏, 阎雪茹, 刘新磊. 苯并咪唑连接聚合物吸附剂和膜研究进展[J]. 化工学报, 2023, 74(2): 599-616.

Figures/Tables 14

Fig.1 Intermolecular forces of benzimidazole-linked polymers

Fig.2 Representative chemical structures of amorphous benzimidazole-linked polymers

Fig.3 Representative chemical structures of crystalline benzimidazole-linked polymers

Fig.4 Synthesis routines of benzimidazole-linked polymers

Fig.5 CO2 adsorption mechanism of benzimidazole-linked polymers[23,27,30]

Table 1 BET surface area， gas uptake and selectivity （CO2/N2 and CO2/CH4） of benzimidazole-linked polymers

聚合物	SA_BET^①/(m²/g)	吸附量^②/(mg/g)			选择性^③		文献
聚合物	SA_BET^①/(m²/g)	CO₂ at 1 bar	N₂at 1 bar	CH₄ at 1 bar	CO₂/N₂	CO₂/CH₄	文献
BILP-1	1172	188（131）	5.0（7.3）	23（16）	70（36）	10（7）	[18]
BILP-2	708	149（104）	3.4（2.5）	14（9）	113（71）	17（12）	[19]
BILP-3	1306	225（145）	3.3（2.4）	24（17）	59（31）	8（5）	[20]
BILP-4	1135	235（158）	1.1（3.8）	26（18）	79（32）	10（7）	[19]
BILP-5	599	128（87）	0.2（2.7）	15（10）	95（36）	10（6）	[19]
BILP-6	1261	211（121）	6.8（6.7）	27（19）	63（39）	8（5）	[20]
BILP-6-NH₂	1185	244.8（164.7）	—	—	—	—（8.4）	[27]
BILP-7	1122	193（122）	5.63（5.40）	19（12）	62（34）	9（7）	[19]
BILP-10	787	177（111）	—	16（11）	111（59）	14（7）	[21]
BILP-11	658	136（88）	—	16（10）	103（55）	11（7）	[22]
BILP-12	1497	223（140）	—	24（15）	56（31）	8（6）	[22]
BILP-13	677	113（79）	—	12（9）	103（38）	9（6）	[22]
BILP-14	1005	170（—）	—	—	56（49）	10（9）	[23]
BILP-15	448	118（80）	5.7（3.8）	13.5（7.2）	83（63）	9（8）	[24]
BILP-16	435	118.7（80.7）	6.5（4.3）	13.5（8.0）	53（49）	10（8）	[24]
BILP-15（AC）	862	151（101）	7.2（5.8）	16.4（10.3）	61（50）	9（7）	[24]
BILP-16（AC）	643	152（102.2）	8.0（4.8）	17.4（10.3）	49（61）	9（7）	[24]
BILP-17	952	—	—	—	—	—	[47]
BILP-18	947	—	—	—	—	—	[47]
BILP-19	144	263^0.95bar（229）	—（3）	14.1（8.2）	—（59.1）	11.9（12.3）	[25]
BILP-101	$536 N 2$	—（107^0.15bar）	—	—	—（80）	—	[26]
PPN-101	$1096 N 2$	226.2（—）	—	—	199（—）	—	[48]
IBFNP-1	$1040 N 2$	232（148）	—	—	65（44）	11（8）	[33]
IBLP	48.06	46.5（30.7）	—	—	—	—	[34]
IBLP-600	161.06	85.1（59.9）	—	—	—	—	[34]
IBLP-700	270.64	121.8（90.7）	—	—	—	—	[34]
IBLP-800	339	130.4（98.4）	—	—	—	—	[34]
BINP-1	64	7.8（—）	—	—	—	—	[49]
BINP-2	32	7（—）	—	—	—	—	[49]
TBILP-1	330	117（78）	—	—	—（63）	—（9）	[28]
TBILP-2	1080	228（146）	—	—	—（40）	—（7）	[28]
CTF-BI-3	677	77.5^1.1bar（—）	1.4（—）	—	88.5（—）	—	[29]
CTF-BI-4	1025	108.7（—）	7.1（—）	—	44.0（—）	—	[29]
CTF-BI-5	836	100.6（—）	6.9（—）	—	35.6（—）	—	[29]
CTF-BI-6	759	75.2（—）	6.3（—）	—	34.5（—）	—	[29]
CTF-BI-7	642	56.3（—）	5.3（—）	—	39.7（—）	—	[29]
CTF-BI-9	885	96.1（—）	5.4（—）	—	67.4（—）	—	[29]
CTF-BI-10	1099	99.9（—）	9.0（—）	—	31.3（—）	—	[29]
CTF-BI-11	1549	110.5（—）	9.6（—）	—	34.3（—）	—	[29]
CTF-BIB-1	$1636 N 2$	97.6（56.8）	10.3（5.1）	30.3（16.2）	29.3（—）	6.8（—）	[30]
CTF-BIB-2	1714	92.3（55.6）	10.0（5.3）	31.9（17.5）	33.1（—）	7.3（—）	[30]
CTF-BIB-3	2088	86.4（48.5）	9.8（3.9）	27.3（16.2）	21.2（—）	4.7（—）	[30]
CTF-DI-2	420	33.5（19.3）	—	—	35（—）	14（—）	[31]
CTF-DI-3	1877	80.4（44.7）	—	—	26（—）	6（—）	[31]
CTF-DI-4	1769	67.6（39.3）	—	—	42（—）	8（—）	[31]
CTF-DI-5	1207	50.9（29.4）	—	—	27（—）	6（—）	[31]
CTF-DI-6	697	62.8（40.0）	—	—	53（—）	15（—）	[31]
CTF-DI-7	1300	89.2（54.2）	—	—	41（—）	11（—）	[31]
CTF-DI-8	1749	77.8（44.5）	—	—	35（—）	8（—）	[31]
CTF-DI-9	1228	59.7（35.4）	—	—	14（—）	6（—）	[31]
PBILP	$557 N 2$	121.4（79.2）	—	—	72（—）	7.2（—）	[32]

Table 1 BET surface area， gas uptake and selectivity （CO2/N2 and CO2/CH4） of benzimidazole-linked polymers

聚合物	SA_BET^①/(m²/g)	吸附量^②/(mg/g)			选择性^③		文献
聚合物	SA_BET^①/(m²/g)	CO₂ at 1 bar	N₂at 1 bar	CH₄ at 1 bar	CO₂/N₂	CO₂/CH₄	文献
BILP-1	1172	188（131）	5.0（7.3）	23（16）	70（36）	10（7）	[18]
BILP-2	708	149（104）	3.4（2.5）	14（9）	113（71）	17（12）	[19]
BILP-3	1306	225（145）	3.3（2.4）	24（17）	59（31）	8（5）	[20]
BILP-4	1135	235（158）	1.1（3.8）	26（18）	79（32）	10（7）	[19]
BILP-5	599	128（87）	0.2（2.7）	15（10）	95（36）	10（6）	[19]
BILP-6	1261	211（121）	6.8（6.7）	27（19）	63（39）	8（5）	[20]
BILP-6-NH₂	1185	244.8（164.7）	—	—	—	—（8.4）	[27]
BILP-7	1122	193（122）	5.63（5.40）	19（12）	62（34）	9（7）	[19]
BILP-10	787	177（111）	—	16（11）	111（59）	14（7）	[21]
BILP-11	658	136（88）	—	16（10）	103（55）	11（7）	[22]
BILP-12	1497	223（140）	—	24（15）	56（31）	8（6）	[22]
BILP-13	677	113（79）	—	12（9）	103（38）	9（6）	[22]
BILP-14	1005	170（—）	—	—	56（49）	10（9）	[23]
BILP-15	448	118（80）	5.7（3.8）	13.5（7.2）	83（63）	9（8）	[24]
BILP-16	435	118.7（80.7）	6.5（4.3）	13.5（8.0）	53（49）	10（8）	[24]
BILP-15（AC）	862	151（101）	7.2（5.8）	16.4（10.3）	61（50）	9（7）	[24]
BILP-16（AC）	643	152（102.2）	8.0（4.8）	17.4（10.3）	49（61）	9（7）	[24]
BILP-17	952	—	—	—	—	—	[47]
BILP-18	947	—	—	—	—	—	[47]
BILP-19	144	263^0.95bar（229）	—（3）	14.1（8.2）	—（59.1）	11.9（12.3）	[25]
BILP-101	$536 N 2$	—（107^0.15bar）	—	—	—（80）	—	[26]
PPN-101	$1096 N 2$	226.2（—）	—	—	199（—）	—	[48]
IBFNP-1	$1040 N 2$	232（148）	—	—	65（44）	11（8）	[33]
IBLP	48.06	46.5（30.7）	—	—	—	—	[34]
IBLP-600	161.06	85.1（59.9）	—	—	—	—	[34]
IBLP-700	270.64	121.8（90.7）	—	—	—	—	[34]
IBLP-800	339	130.4（98.4）	—	—	—	—	[34]
BINP-1	64	7.8（—）	—	—	—	—	[49]
BINP-2	32	7（—）	—	—	—	—	[49]
TBILP-1	330	117（78）	—	—	—（63）	—（9）	[28]
TBILP-2	1080	228（146）	—	—	—（40）	—（7）	[28]
CTF-BI-3	677	77.5^1.1bar（—）	1.4（—）	—	88.5（—）	—	[29]
CTF-BI-4	1025	108.7（—）	7.1（—）	—	44.0（—）	—	[29]
CTF-BI-5	836	100.6（—）	6.9（—）	—	35.6（—）	—	[29]
CTF-BI-6	759	75.2（—）	6.3（—）	—	34.5（—）	—	[29]
CTF-BI-7	642	56.3（—）	5.3（—）	—	39.7（—）	—	[29]
CTF-BI-9	885	96.1（—）	5.4（—）	—	67.4（—）	—	[29]
CTF-BI-10	1099	99.9（—）	9.0（—）	—	31.3（—）	—	[29]
CTF-BI-11	1549	110.5（—）	9.6（—）	—	34.3（—）	—	[29]
CTF-BIB-1	$1636 N 2$	97.6（56.8）	10.3（5.1）	30.3（16.2）	29.3（—）	6.8（—）	[30]
CTF-BIB-2	1714	92.3（55.6）	10.0（5.3）	31.9（17.5）	33.1（—）	7.3（—）	[30]
CTF-BIB-3	2088	86.4（48.5）	9.8（3.9）	27.3（16.2）	21.2（—）	4.7（—）	[30]
CTF-DI-2	420	33.5（19.3）	—	—	35（—）	14（—）	[31]
CTF-DI-3	1877	80.4（44.7）	—	—	26（—）	6（—）	[31]
CTF-DI-4	1769	67.6（39.3）	—	—	42（—）	8（—）	[31]
CTF-DI-5	1207	50.9（29.4）	—	—	27（—）	6（—）	[31]
CTF-DI-6	697	62.8（40.0）	—	—	53（—）	15（—）	[31]
CTF-DI-7	1300	89.2（54.2）	—	—	41（—）	11（—）	[31]
CTF-DI-8	1749	77.8（44.5）	—	—	35（—）	8（—）	[31]
CTF-DI-9	1228	59.7（35.4）	—	—	14（—）	6（—）	[31]
PBILP	$557 N 2$	121.4（79.2）	—	—	72（—）	7.2（—）	[32]

Fig.6 CO2 adsorption capacity and CO2/N2 selectivity of benzimidazole-linked polymers

Fig.7 Ion adsorption mechanism of benzimidazole-linked polymers[56-57]

Fig.8 Fabrication of benzimidazole-linked polymer membranes

Fig.9 Separation mechanism of benzimidazole-linked polymer gas separation and nanofiltration membranes

Fig.10 Separation mechanism of benzimidazole-linked polymer proton transfer membranes[63]

Fig.11 Separation performance of benzimidazole-linked polymers membranes

Table 2 Proton conductivity of benzimidazole-linked polymers and commercial Nafion membranes

聚合物	电导率 σ/(S/cm)	温度 T/K	湿度 RH/%	活化能 E_a/eV	文献
DPBIB	9.3 $×$ 10^-2	393	100	—	[17]
PON-4	9.7 $×$ 10^-6	393	0	0.6	[96]
PON-5	2.0 $×$ 10^-5	393	0	0.36	[96]
PON-6	4.9 $×$ 10^-6	393	0	0.46	[96]
BIP	3.2 $×$ 10^-2	368	95	0.34	[35]
BILP-10	1.2 $×$ 10^-4	368	95	—	[35]
Im@TP-DADMB	2.4 $×$ 10^-3	393	0	0.16	[95]
H₃PO₄@TPB-DABI-COF[66%（质量分数）]	1.52 $×$ 10^-1	433	0	0.17	[36]
Nafion 112	9.4 $×$ 10^-2	393	100	—	[97]
Nafion 115	1.3 $×$ 10^-1	363	100	—	[98]
Nafion 117	4.5 $×$ 10^-2	383	0	—	[99]

Table 2 Proton conductivity of benzimidazole-linked polymers and commercial Nafion membranes

聚合物	电导率 σ/(S/cm)	温度 T/K	湿度 RH/%	活化能 E_a/eV	文献
DPBIB	9.3 $×$ 10^-2	393	100	—	[17]
PON-4	9.7 $×$ 10^-6	393	0	0.6	[96]
PON-5	2.0 $×$ 10^-5	393	0	0.36	[96]
PON-6	4.9 $×$ 10^-6	393	0	0.46	[96]
BIP	3.2 $×$ 10^-2	368	95	0.34	[35]
BILP-10	1.2 $×$ 10^-4	368	95	—	[35]
Im@TP-DADMB	2.4 $×$ 10^-3	393	0	0.16	[95]
H₃PO₄@TPB-DABI-COF[66%（质量分数）]	1.52 $×$ 10^-1	433	0	0.17	[36]
Nafion 112	9.4 $×$ 10^-2	393	100	—	[97]
Nafion 115	1.3 $×$ 10^-1	363	100	—	[98]
Nafion 117	4.5 $×$ 10^-2	383	0	—	[99]

Fig.12 Proton conductivity of benzimidazole-linked polymers and commercial Nafion membranes

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