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

Polymer	Young’s modulus(MPa)	Tensile strength (MPa)	Elongation at break (%)	T_d(℃)	Fenton’s reagent test^a)	ref
sPPP-H⁺	1059	43.5	29.1	—	Dissolve after 3 h	65
sPPB-H⁺	1331	59.6	17.5	260	Intact after 1 h	66
sPPN-H⁺	1170	53.3	18.7	260	Intact after 1 h	66
sPPP (m)-H⁺	1008~1407	39.6~51.3	15.9~31.7	—	Broken after 3 h	67
sPPB (x% DB)-H⁺	1267~1616	52.8~62.1	12.9~26.3	280	Intact after 1 h	70
sTPPPP-H⁺	584.1	54.8	36.8	246	Completely dissolved after 5.3 h	71
sTPPyPP-H⁺	401.8	43.3	55.5	326	There are still residues after 6.3 h	71

Table 2 Young’s modulus, tensile strength, elongation at break, thermal decomposition temperature and Fenton’s reagent test of some phenylated polyphenylenes

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

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