Progress in Chemistry

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Proton Exchange Membranes Based on All-Carbon Backbone Aromatic Polymers

Li Tingting, Li Haibin, Liu Binghui, Zhao Chengji, Li Haolong

Prog Chem, 2023, 35(11): 1559-1578. DOI: 10.7536/PC230513

Structures	Fenton’s reagent	Temperature(℃)	Test Results	ref
PBP	3% H₂O₂,3 ppm Fe²⁺	68	Broken after 26 h	111
PTP	3% H₂O₂,3 ppm Fe²⁺	68	Broken after 200 h	111
PTP-TFA	3% H₂O₂,4 ppm Fe²⁺	68	Mass loss of 17% after 84 h	112
PTP-35%Me	3% H₂O₂,4 ppm Fe²⁺	68	Mass loss of 20% after 84 h	112
PTP-33%Py	3% H₂O₂,4 ppm Fe²⁺	68	Mass loss of 30% after 84 h	112
PTP-41%BeIm	3% H₂O₂,4 ppm Fe²⁺	68	Mass loss of 35% after 84 h	112
PBAP	3% H₂O₂,4 ppm Fe²⁺	68	Broken after 75 h	113
PTAP	3%H₂O₂,4 ppm Fe²⁺	68	Polymer membrane remains intact after 450 h	113
2-IMPIM	3% H₂O₂,2 ppm Fe²⁺	80	Mass loss of 19% at 50 h	116
4-IMPIM	3% H₂O₂,2 ppm Fe²⁺	80	Mass loss of 13% for 50 h	116
MFxDPy-PS、HFxDPy-PS	3% H₂O₂,4 ppm Fe²⁺	80	All polymer membranes remain intact after 10 days	95
BPSA	3% H₂O₂,2 ppm Fe²⁺	80	Mass loss of 2% for 1 h	98
m-TPSA	3% H₂O₂,2 ppm Fe²⁺	80	Mass loss of 1% for 1 h	98
Poly(FLx-BPy)-SO₃H	—	80	The mass loss of all polymer membranes was less than 1% after 4 h	99
	3% H₂O₂,2 ppm Fe²⁺	80	Broken after 24 h	100
SP100
SMn-X-IEC	3% H₂O₂,2 ppm Fe²⁺	80	The signal peak of side chain fluorine decreased about 70% after 1 h	101
SP1	3% H₂O₂,2 ppm Fe²⁺	80	Broken after 6 h	90
SP2	3% H₂O₂,2 ppm Fe²⁺	80	Broken after 8.5 h	90
SP3	3% H₂O₂,2 ppm Fe²⁺	80	Broken after 10.5 h	90
PPx	3% H₂O₂,2 ppm Fe²⁺	80	PP55, PP72, PP83 membranes become opaque after 11 days	118

Table 3 Fenton’s reagent test of some poly(arylene-alkane) proton exchange membranes

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Table 1 Typical structures and synthesis methods of polyphenylenes, phenylated polyphenylenes and poly(arylene-alkane)s
Fig.1 Polyphenylenes was synthesized by coupling reaction induced by nickel catalysts^{[36,42,43,45,46]}
Fig.2 Sulfonated polyphenylenes was synthesized by Ullmann coupling reaction^[44]
Fig.3 Chemical structures of some polyphenylenes: (a) PBPDSA, (b) PPDSA, (c) BXPY, (d) PPDSA-g-DDB3-24%, PPDSA-g-OcB11-16% and B20P80-g-OcB7-18%, (e) B20P80-g-BP10%-210C-3h^[44,47,48]
Fig.4 Chemical structure of (a) SPP-BP-CH₃ and SPP-BP-CF₃ (b) SBAF^[49,51]
Fig.5 Chemical structures of (a) SPP-QP and (b) SPP-BP^[42,54]
Fig.6 Synthesis of QP monomer^[42]
Fig.7 (a) Synthesis of phenylated polyphenylenes by Diels-Alder condensation, (b) synthesis of 1,4-bis(2,4,5-triphenylcyclopentadienone)benzene^{[58⇓⇓~61]}
Fig.8 Synthesis of phenylated polyphenylene sPPP-H⁺ by pre-sulfonated monomer approach^[65]
Fig.9 Chemical structure of some phenylated polyphenylenes: (a) sPPB-H⁺, (b) sPPN-H⁺, (c) sPPB (x% DB)-H⁺, (d) sTPPyPP-H^+[66,70~72]
Table 2 Young’s modulus, tensile strength, elongation at break, thermal decomposition temperature and Fenton’s reagent test of some phenylated polyphenylenes
Fig.10 Chemical structure of PA-doped QAPOH^[75]
Fig.11 Synthesis of poly(arylene-alkane)s by Friedel-Crafts reaction^{[83⇓~85,87,89,90]}
Fig.12 Several methods of sulfonation of poly(arylene-alkane)s^{[90,94⇓~96,98⇓⇓ ~101]}
Fig.13 Fenton’s reagent test of PPx membranes at 80℃: (a) initial state and after 5 h, and (b) after 260 h^[110]
Fig.14 Synthesis of the PTP polymer and the subsequent grafting with different quaternized reagents^[112]

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