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Progress in Chemistry 2020, Vol. 32 Issue (2/3): 190-203 DOI: 10.7536/PC190613 Previous Articles   Next Articles

Special Issue: 电化学有机合成

Synthesis and Properties of Microporous Organic Polymers Based on Adamantane

Li Liangjun, Jianhui Deng, Jianwei Guo**(), Hangbo Yue**()   

  1. School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China
  • Received: Online: Published:
  • Contact: Jianwei Guo, Hangbo Yue
  • About author:
    ** e-mail: (Jianwei Guo);
    (Hangbo Yue)
  • Supported by:
    National Natural Science Foundation of China(21476051); National Natural Science Foundation of China(21706039); Natural Science Foundation of Guangdong Province(2017A030310300); Natural Science Foundation of Guangdong Province(2016A030310349); Science and Technology Program of Guangzhou City(201704030075); Degree and Graduate Education Reform Research Program of Guangdong Province(2017QTLXXM12)
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Microporous organic polymers(MOPs) is one of the most promising new materials for many applications, such as gas capture and storage, gas separation, organic vapor adsorption, heterogeneous catalyst carrier, water treatment, functional materials and so on, making them to be a research hotspot. This is due to the fact that MOPs have shown many advantages in, for example, excellent thermal stability, chemical stability, low density, high specific surface area, and molecular pore size architecture. Generally, molecular building blocks, particularly being symmetrical in plane or space, are the core architecture in the synthesis of MOPs. Among various building molecules, multi-substituted adamantane, has been reported as a new molecular "knot" candidate for the creation of MOPs, by connecting with a "linkage" molecule, thanks to its highly stereoscopic symmetrical structure and structural rigidity. In addition, the adamantane-based MOPs have shown many advantageous and interesting properties in terms of synthetic yield, structural stability, pore size distribution, gas/vapor adsorption and separation. This mini review focuses on recent progress in the synthesis and interesting properties of the MOPs with adamantane incorporated(MOP-Ad). The MOP-Ad polymers are classified into phenyl-linkage, Schiff base linkage, imide linkage, and nitrogen-rich(benzimidazole and triazine) categories. Special attention is paid to the similarities and differences with comparison in the synthetic route, structural characteristics, stability and adsorption properties. Besides, some emerging new types of Ad-polymers are briefly introduced and an outlook is also proposed for the MOP-Ad.

Key words: adamantane, microporous organic polymers, synthesis, properties
Fig.1 Different molecular knots and rods for MOP-Ad synthesis
Table 1 Properties of MOP-Ad for different linkage types
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
Fig.2 (a) Synthesis of MOP-Ad networks and (b) cartoon 3D representations of the networks in each case[28].(i) Tetrakis(triphenylphosphine) palladium(0) and K2CO3(aq.) were added, degassed by purging argon, and stirred at 150 ℃ for 72 h. Copyright 2017, RSC
Fig.3 Synthesis of (a) dual-adamantane frameworks with static-determined structure(HBPBA) [31] and (b) adamantane-based frameworks with conjugated π-electron skeletons(CMF-Ad)[32]. Copyright 2017&2018, Elsevier
Fig.4 Synthesis of Schiff base PSN-1、PSN-2、PSN-3[40,41]
Fig.5 Synthesis of adamatane-based polyimide[49,50,51]
Fig.6 Synthesis of the microporous polybenzimidazole networks(PBI-Ad)[36]. Copyright 2015, ACS
Fig.7 Synthesis of porous covalent triazine-based frameworks PCTF-3 to PCTF-7[55]. Copyright 2013, RSC
Table 2 Performance comparison on MOP-Ad incorporating nitrogen
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
Fig.8 Synthetic procedure of disubstituted adamantine-based oxacyclophanes[67]. Copyright 2015, ACS
Fig.9 Synthesis of tetrasubstituted adamantanes and process of incorporating small molecules[68]. Copyright 2015, Wiley
Fig.10 Structure of multi-substituted diphenylphosphate adamantane[70]
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