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Progress in Chemistry 2023, Vol. 35 Issue (11): 1559-1578 DOI: 10.7536/PC230513   Next Articles

• Review •

Proton Exchange Membranes Based on All-Carbon Backbone Aromatic Polymers

Li Tingting1, Li Haibin1, Liu Binghui2, Zhao Chengji2, Li Haolong1,2()   

  1. 1 State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University,Changchun 130012, China
    2 Key Laboratory of High Performance Plastics, Ministry of Education, College of Chemistry, Jilin University,Changchun 130012, China
  • Received: Revised: Online: Published:
  • Contact: Li Haolong
  • Supported by:
    National Natural Science Foundation of China(92261110); National Natural Science Foundation of China(22075097)
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Proton exchange membranes are widely used in energy storage and conversion technologies such as fuel cells, redox flow batteries, and water electrolysis, which are key materials urgently needed under the “dual carbon” goal. Perfluorosulfonic acid membranes show high proton conductivity and mechanical properties, which are currently the most widely used proton exchange membranes materials. However, these membranes suffer from the following disadvantages, such as greatly decreased proton conductivity at low humidity conditions, low glass transition temperature, and complex synthesis process. In the past decades, efforts have been devoted to the development of various alternative materials, such as polyether ether ketone, polyphenylene oxide, polysulfone and polyimide. However, the main chains of these polymers usually contain heteroatoms. Upon working in a complex practical condition for a long time, the heteroatom position is prone to break, which reduces the chemical stability of these materials. In contrast, the all-carbon backbone aromatic polymers have excellent chemical stability, thermal stability, and mechanical properties, and are a class of potential alternative materials that have attracted extensive attention in recent years. In this review paper, we summarize the recent research progress of all-carbon backbone aromatic polymers, focusing on the synthesis strategies, structure-performance relationships, as well as the applications of these polymers in proton exchange membranes.

Contents

1 Introduction

2 Proton exchange membranes based on polyphenylenes

2.1 Synthesis and general properties

2.2 Straight-chain sulfonated polyphenylene proton exchange membranes

2.3 Curve-chain sulfonated polyphenylene proton exchange membranes

3 Proton exchange membranes based on phenylated polyphenylenes

3.1 Synthesis and general properties

3.2 Sulfonated phenylated polyphenylene proton exchange membranes

3.3 Phosphoric acid doped phenylated polyphenylene proton exchange membranes

4 Proton exchange membranes based on poly(arylene-alkane)s

4.1 Synthesis and general properties

4.2 Sulfonated poly(arylene-alkane) proton exchange membranes

4.3 Phosphorylated poly(arylene-alkane) proton exchange membranes

4.4 Phosphoric acid doped poly(arylene-alkane) proton exchange membranes

5 Conclusion and outlook

Key words: proton exchange membranes, all-carbon backbone aromatic polymers, proton conductivity, chemical stability, structure-performance relationships
Table 1 Typical structures and synthesis methods of polyphenylenes, phenylated polyphenylenes and poly(arylene-alkane)s
Category Structure Synthesis methods ref
42
Polyphenylenes Coupling reaction 44


Phenylated polyphenylenes

Diels-Alder reaction
65




70
Poly(arylene-alkane)s Friedel-Crafts 100


111
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
Polymer Young’s
modulus(MPa)		 Tensile strength
(MPa)		 Elongation at
break (%)		 Td(℃) Fenton’s reagent testa) 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
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
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
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