所属专题: 电化学有机合成
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李梁君, 邓建辉, 郭建维, 岳航勃. 金刚烷基微孔有机聚合物的合成与性能[J]. 化学进展, 2020, 32(2/3): 190-203.
Li Liangjun, Jianhui Deng, Jianwei Guo, Hangbo Yue. Synthesis and Properties of Microporous Organic Polymers Based on Adamantane[J]. Progress in Chemistry, 2020, 32(2/3): 190-203.
微孔有机聚合物由于具有优异的热稳定性、化学稳定性、低密度、高比表面积、分子尺度的孔径分布等优点,在气体储存、气体吸附与分离、有机蒸气吸附、异相催化剂载体、水处理、功能材料等方面引起研究者们极大的兴趣。通常,分子构筑单元特别是在平面或空间中呈对称性的单元,是合成微孔有机聚合物的核心单位。在众多的构筑单元或单体中,多取代金刚烷化合物具有高空间对称性和刚性结构特点,已被成功地用作分子“结”与其他多种类型的连接单元(分子“杆”)来构建三维微孔有机聚合物,而且此类微孔有机聚合物在合成产率、结构稳定性、孔径分布、吸附分离等方面表现出许多特殊或优异的性质。本文介绍了目前由金刚烷结构单元构建的以下几种微孔有机聚合物在合成和性能方面的研究进展:苯环连接型、席夫碱连接型、酰亚胺连接型、富氮型(苯并咪唑和三嗪),详细分析和比较了这些聚合物在合成方法、结构特点、稳定性与吸附性能等方面的异同点。此外,介绍了几种其他新型的金刚烷基聚合物。最后提出基于金刚烷的微孔有机聚合物未来的研究方向与思路。
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Type | Material | Knots & Rods | BET surface area(m2·g-1) | Pore size (nm) | H2 uptake (wt%) | Special Properties | ref | ||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Phenyl | CMP-3 | K1+K1 | 3108 | 1.4 | 2.34a | SABET=3108 m2·g-1 | 23 | ||||||
-linkage | MOP-Ad-1 | K1+R1 | 974 | 0.74 | 1.07a | Thermal stability:≈520 ℃ | 28 | ||||||
MOP-Ad-2 | K1+R2 | 653 | 0.55 | 0.92a | Thermal stability:≈520 ℃ | 28 | |||||||
MOP-Ad-3 | K1+R3 | 282 | 0.52 | 0.49a | Thermal stability:≈520 ℃ | 28 | |||||||
TBPAd-T | K1+R4 | 654 | 0.87 | 0.60a | Thermal stability:≈500 ℃ | 29 | |||||||
Trandafir’s COF | K2+R5 | 577 | 0.8 | 0.05b | Au or Pd carrier for catalyst; Thermal stability:≈300 ℃ | 30 | |||||||
HBPBA-1 | K3+R6 | 742 | 0.4~0.6 | 1.11~1.16a | Hexaphenylbiadamantane-based unit; Thermal stability:≈480 ℃ | 31 | |||||||
HBPBA-2 | K3+R7 | 760 | 0.4~0.6 | 1.11~1.16a | Hexaphenylbiadamantane-based unit; Thermal stability:≈480 ℃ | 31 | |||||||
HBPBA-3 | K3+R8 | 891 | 0.4~0.6 | 1.11~1.16a | Hexaphenylbiadamantane-based unit; Thermal stability:≈480 ℃ | 31 | |||||||
HBPBA-D | K3+R9 | 488 | 0.92~1.1 | - | Hexaphenylbiadamantane-based unit; Thermal stability:≈480 ℃ | 37 | |||||||
TBBPA-D | K4+R9 | 395 | 0.42 | - | Eight-arm tetraphenyl “knots”; Thermal stability:≈372 ℃ | 37 | |||||||
CMF-Ad-1 | K4+R1 | 907 | 0.73 | 1.44a | Eight-arm tetraphenyl “knot”; π-conjugated skeleton; high yield=95.1% | 32 | |||||||
CMF-Ad-2 | K4+R2 | 765 | 0.51 | 1.15a | Eight-arm tetraphenyl “knot”; π-conjugated skeleton; high yield=90.8% | 32 | |||||||
CMF-Ad-3 | K4+R3 | 604 | 0.86 | 1.22a | Eight-arm tetraphenyl “knot”; π-conjugated skeleton; high yield=87.7% | 32 | |||||||
Type | Material | Knots & Rods | BET surface area(m2·g-1) | Pore size (nm) | H2 uptake (wt%) | Special Properties | ref | ||||||
Schiff base linkage | PSN-1 | K5+R10 | 1045 | 0.7 | 1.26a | Structure-directing effect of isomers; Pore volume=0.86 cm3·g-1 | 40 | ||||||
PSN-2 | K5+R11 | 376 | 2.2 | 0.90a | Structure-directing effect of isomers; Pore size=2.2 nm | 40 | |||||||
PSN-3 | K5+K6 | 865 | 0.6 | 1.32a | Benzene=80.5 wt%c; Cyclohexane= 63.7 wt%c; Pore volume=0.83 cm3·g-1 | 41 | |||||||
COF-MA | K5+K6 | 813 | 0.57 | - | Long range order | 42 | |||||||
Imide | sPI-1 | K6+R12 | 1108 | 0.60 | 2.50a | CO2=23.7 wt%e, Benzene=159.7 wt%c | 51 | ||||||
linkage | PI-ADPM | K6+R13 | 862 | 1.06~1.34 | 1.27a | Benzene=99.2 wt%c; Cyclohexane =59.7 wt%c | 49 | ||||||
PI-ADNT | K6+R14 | 774 | 0.75 | - | Thermal stability:=621 ℃ | 50 | |||||||
PI-NO2-1,2,3 | K6+R14 | 286(max) | 0.57~0.75 | - | Nitration modification; Max selectivity (CO2/CH4)=21f | 50 | |||||||
Nitrogen-rich | |||||||||||||
Benzimidazole | PBI-Ad-1 | K5+R15 | 1023 | 0.58 | 1.60a | Selectivity:(CO2/N2)=71f; Benzene= 98 wt%d; Cyclohexane=53.6 wt%d | 36 | ||||||
PBI-Ad-2 | K5+R16 | 926 | 0.60 | 1.30a | Selectivity:(CO2/N2)=70f; Benzene= 76.5 wt%d; Cyclohexane=46.3 wt%d | 36 | |||||||
Triazine | PCTF-5 | K7+K7 | 1183 | 1 | 1.24a | Thermal stability: ≈500 ℃ | 55 | ||||||
PCN-AD | K8+K8 | 843 | 0.78 | 1.49a | Selectivity:(CO2/N2)=112f; Benzene= 98 wt%c; Cyclohexane=57.4 wt%c | 54 | |||||||
Other types | Adamantane-based oxacyclophanes | K9+R17 | - | - | - | Macrocyclic framework | 67 | ||||||
TDA | K10+R18 | - | - | - | Carrier for small molecules: CH3Cl, n-hexane, ethanol, etc. | 68 | |||||||
TKDPAd | K10+R19 | - | - | - | Flame retardants; PC/TKDPAd(8 wt%) UL-94 V-0 | 70 |
Type | Material | Preparation | Structure properties | Adsorption properties | ref | |||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Morphology (by XRD/SEM) | BET surface area (m2·g-1) | Pore size (nm) | Vtotal (cm3·g-1) | Vmicro (cm3·g-1) | Vmicro/Vtotal (%) | CO2 uptake (wt%) | C6H6 uptake(wt%) | C6H12 uptake(wt%) | ||||||
Schiff | PSN-1 | Condensation of aldehyde and amine | amorphous | 1045 | 0.7 | 0.86 | 0.27 | 31.40 | 15e | - | - | 40 | ||
base linkage | PSN-2 | amorphous | 376 | 2.2 | 0.39 | 0.05 | 12.82 | 6.7e | - | - | 40 | |||
PSN-3 | amorphous | 865 | 0.6 | 0.83 | - | 13.6e | 80.5c | 63.7c | 41 | |||||
COF-MA | long range order | 813 | 0.57 | 0.41 | 0.57 | 75.61 | 14.4e | - | - | 42 | ||||
Imide linkage | sPI-1 | Condensation of amine and anhydride | amorphous | 1108 | 0.91 | 0.91 | 0.20 | 21.98 | 23.7e | 159.7c | 85.1c | 51 | ||
PI-ADPM | - | 862 | 1.06~1.34 | 0.372 | 0.319 | 85.75 | 14.6e | 99.2c | 59.7c | 49 | ||||
PI-ADNT | - | 774 | 0.75 | 0.75 | 0.163 | 21.73 | 15e | - | - | 50 | ||||
PI-NO2-1,2,3 | - | 286(max) | 0.75(max) | 0.155(max) | - | - | 17.7(max)e | - | - | 50 | ||||
Nitrogen-rich | ||||||||||||||
Benzimida zole | PBI-Ad-1 PBI-Ad-2 | Cyclization of aldehyde and amine | amorphous | 1023 | 0.58 | 0.64 | 0.32 | 50.00 | 17.3e | 98d | 53.6d | 36 | ||
amorphous | 926 | 0.60 | 0.73 | 0.24 | 32.88 | 13.7e | 76.5d | 46.3d | 36 | |||||
Nitrile trimerization(ionothermal reaction) | amorphous | 1183 | 1 | 0.7 | 0.45 | 64.29 | 11e | - | - | 55 | ||||
Triazine | PCTF-5 PCN-AD | |||||||||||||
amorphous | 843 | 0.78 | 0.62 | 0.08 | 12.90 | 12.8e | 98c | 57.4c | 54 |
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