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Lewis Acid−Base Pairs for Polymerization Catalysis: Recent Progress and Perspectives

  • Miao HongEmail author
Chapter
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Part of the Molecular Catalysis book series (MOLCAT, volume 2)

Abstract

Lewis pair polymerization (LPP), catalyzed by frustrated Lewis pairs (FLPs), interacting LPs (ILPs), or classical Lewis adducts (CLAs), has become a very powerful tool for efficient, controlled, and selective polymerizations of heteroatom-containing polar monomers since its inception in 2010. The unique cooperative/synergetic monomer activation by both Lewis acid (LA) and Lewis base (LB) sites of LP catalysts not only gives this new polymerization methodology a high visibility from the beginning, but also brings about a variety of novel polymeric materials that cannot be efficiently realized by traditional polymerization techniques. This chapter highlights the very recent progress made in this rapidly expanding field since the last comprehensive review in 2018, with a special emphasis on the LP-mediated polymerization of polar vinyl monomers and ring-opening (co)polymerization of cyclic esters and epoxides.

Keywords

Lewis pair polymerization Frustrated Lewis pair Classical Lewis adduct Ring-opening polymerization Polar vinyl monomer 

Abbreviations

β-AL

β-angelica lactone (Scheme 8.12)

AGE

Allyl glycidyl ether (Scheme 8.15)

AMA

Allyl methacrylate (Scheme 8.1)

BDM

1,4-benzenedimethanol (Scheme 8.16)

BHT

Butylated hydroxytoluene

BO

1,2-Butylene oxide (Scheme 8.15)

nBA

n-Butyl acrylate (Scheme 8.8)

tBA

tert-Butyl acrylate (Scheme 8.8)

Conv.%

Conversion

CLA

Classical Lewis adduct

ε-CL

ε-Caprolactone (Scheme 8.1)

DCM

Dichloromethane

DHDM

Double high and double multiple

DMAA

N,N-Dimethyl acrylamide (Scheme 8.1)

Ð

Molecular weight distribution/dispersity

EO

Ethylene oxide (Schemes 8.15)

EMA

Ethyl methacrylate

FLP

Frustrated Lewis pairs

3-F-Py

3-Fluoropyridine (Scheme 8.14)

IN

Indenone (Scheme 8.11)

LPP

Lewis pair polymerization

l-LA

l-Lactide (Scheme 8.1)

MC

Methyl crotonate (Scheme 8.10)

ILP

Interacting Lewis pairs

LB

Lewis base

LA

Lewis acid

MBL
α-Methylene-γ-butyrolactone (Scheme 8.1)
Scheme 8.1

An equilibrium between CLAs, ILPs, and FLPs (a); A generic chain initiation step to generate the zwitterionic active species and subsequent propagation steps to produce polymer products in LPP of polar vinyl monomers (b) and in LP-mediated ROP of cyclic esters (c); A list of selected monomers investigated in the previous LPPs (d)

MS

(E,E)-Methyl sorbate (Scheme 8.1)

NHC

N‑Heterocyclic carbene

NHO

N-Heterocyclic olefin

OCA

O-Carboxyanhydrides (Scheme 8.13, 8.14)

PO

Propylene oxide (Scheme 8.15)

PDL

ω-Pentadecalactone (Scheme 8.1)

PT

Pentaerythritol (Scheme 8.16)

RO(C)P

Ring-opening (co)polymerization

RT

Room temperature

SFMA

Semifluorinated methacrylate

Tg

Glass transition temperature

Td

Onset degradation temperature

Tm

Melting temperature

THF

Tetrahydrofuran

TBD

1,5,7-Triazabicyclododecene (Scheme 8.16)

TBGE

tert-Butyl glycidyl ether (Scheme 8.15)

VBMA

4-Vinylbenzyl methacrylate (Scheme 8.1)

VMA

Vinyl methacrylate (Scheme 8.1)

δ-VL

δ-Valerolactone (Scheme 8.1)

MMA

Methyl methacrylate (Scheme 8.1)

DBU

1,8-Diazabicyclo[5.4.0]undec-7-ene (Scheme 8.16)

ItBu

1,3-Di-tert-butylimidazolin-2-ylidene (Scheme 8.6)

I*

Initiation efficiency = Mn(calcd)/Mn(exptl), where Mn(calcd) = MW(monomer) × [monomer]0/[initiator(catalyst)]0 × conversion (%) + MW(end groups)

γMMBL

γ-Methyl-α-methylene-γ-butyrolactone (Scheme 8.1)

MTBD

7-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (Scheme 8.16)

Mg(HMDS)2

Magnesium bis(hexamethyldisilazide) (Scheme 8.15)

TOF

Turnover frequency = moles of substrate (monomer) consumed per mole of catalyst (initiator) per hour

Notes

Acknowledgments

This work was supported by the National Natural Science Foundation of China (Y8502112G0, E0502112G0, 21821002), the Thousand Talents Plan for Young Scholars of China, and K. C. Wong Education Foundation.

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Authors and Affiliations

  1. 1.State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of SciencesShanghaiChina

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