Polymerized ionic liquids

562 Pages·2018·41.871 MB·English

by  Eftekhari, Ali

Polymerized Ionic Liquids
1
0
0
P
F
5-
3
5
0
1
0
8
8
7
1
8
7
9
9/
3
0
1
0.
1
oi:
d
g |
or
c.
s
s.r
b
u
p
p://
htt
n
o
7
1
0
2
er
b
m
e
pt
e
S
8
n 1
o
d
e
h
s
bli
u
P
View Online
Smart Materials
Series editors:
Hans-Jörg Schneider, Saarland University, Germany
1
00 Mohsen Shahinpoor, University of Maine, USA
P
F
5-
53 Titles in this series:
0
01 1: Janus Particle Synthesis, Self-Assembly and Applications
8
78 2: Smart Materials for Drug Delivery: Volume 1
1
78 3: Smart Materials for Drug Delivery: Volume 2
9
9/ 4: Materials Design Inspired by Nature
3
0
1 5: Responsive Photonic Nanostructures: Smart Nanoscale Optical
0.
oi:1 Materials
g | d 6: Magnetorheology: Advances and Applications
or 7: Functional Nanometer-Sized Clusters of Transition Metals: Synthesis,
sc. Properties and Applications
s.r
b 8: Mechanochromic Fluorescent Materials: Phenomena, Materials and
u
p
p:// Applications
htt 9: Cell Surface Engineering: Fabrication of Functional Nanoshells
n
o 10: Biointerfaces: Where Material Meets Biology
7
01 11: Semiconductor Nanowires: From Next-Generation Electronics to
2
er Sustainable Energy
b
m 12: Supramolecular Materials for Opto-Electronics
e
ept 13: Photocured Materials
S
8 14: Chemoresponsive Materials: Stimulation by Chemical and Biological
on 1 Signals
d
e 15: Functional Metallosupramolecular Materials
h
s
bli 16: Bio-Synthetic Hybrid Materials and Bionanoparticles: A Biological
u
P Chemical Approach Towards Material Science
17: Ionic Polymer Metal Composites (IPMCs): Smart Multi-Functional
Materials and Artificial Muscles Volume 1
18: Ionic Polymer Metal Composites (IPMCs): Smart Multi-Functional
Materials and Artificial Muscles Volume 2
19: Conducting Polymers: Bioinspired Intelligent Materials and Devices
20: Smart Materials for Advanced Environmental Applications
21: Self-cleaning Coatings: Structure, Fabrication and Application
22: Functional Polymer Composites with Nanoclays
23: Bioactive Glasses: Fundamentals, Technology and Applications
24: Smart Materials for Tissue Engineering: Fundamental Principles
View Online
25: Smart Materials for Tissue Engineering: Applications
26: Biobased Smart Polyurethane Nanocomposites: From Synthesis to
Applications
27: Inorganic Two-dimensional Nanomaterials: Fundamental
1
0 Understanding, Characterizations and Energy Applications
0
P
F 28: Ionic Liquid Devices
5-
53 29: Polymerized Ionic Liquids
0
1
0
8
8
7
1
8
7
9
9/
3
0
1
0.
1
oi:
d
g |
or
c.
s
s.r
b
u
p
p://
htt
n
o
7
1
0
2
er
b
m
e
pt
e
S
8
n 1
o
d
e
h
s
bli
u
P
How to obtain future titles on publication:
A standing order plan is available for this series. A standing order will bring
delivery of each new volume immediately on publication.
For further information please contact:
Book Sales Department, Royal Society of Chemistry, Thomas Graham House,
Science Park, Milton Road, Cambridge, CB4 0WF, UK
Telephone: [phone], Fax: [phone]
Email: [email protected]
Visit our website at www.rsc.org/books
View Online
1
0
0
P
F
5-
3
5
0
1
0
8
8
7
1
8
7
9
9/
03
1
0.
1
oi:
d
g |
or
c.
s
s.r
b
u
p
p://
htt
n
o
7
1
0
2
er
b
m
e
pt
e
S
8
n 1
o
d
e
h
s
bli
u
P
View Online
Polymerized Ionic Liquids
1
0
0
P
F
5-
3 Edited by
5
0
1
0
8
8 Ali Eftekhari
7
1
78 Ulster University, Belfast, UK
9
9/ Email: [email protected]
3
0
1
0.
1
oi:
d
g |
or
c.
s
s.r
b
u
p
p://
htt
n
o
7
1
0
2
er
b
m
e
pt
e
S
8
n 1
o
d
e
h
s
bli
u
P
View Online
1
0
0
P
F
5-
3
5
0
1
0
8
8
7
1
8
7
9
9/ Smart Materials No. 29
3
0
1
0. Print ISBN: 978-1-78262-960-3
1
oi: PDF eISBN: 978-1-78801-053-5
d
g | EPUB eISBN: 978-1-78801-221-8
or ISSN: 2046-0066
c.
s
bs.r A catalogue record for this book is available from the British Library
u
p
p:// © The Royal Society of Chemistry 2018
htt
n
7 o All rights reserved
1
0
2
er Apart from fair dealing for the purposes of research for non-commercial purposes or for
mb private study, criticism or review, as permitted under the Copyright, Designs and Patents
e
pt Act 1988 and the Copyright and Related Rights Regulations 2003, this publication may
e
S not be reproduced, stored or transmitted, in any form or by any means, without the prior
8
n 1 permission in writing of The Royal Society of Chemistry or the copyright owner, or in
d o the case of reproduction in accordance with the terms of licences issued by the Copyright
e
h Licensing Agency in the UK, or in accordance with the terms of the licences issued by the
s
bli appropriate Reproduction Rights Organization outside the UK. Enquiries concerning
u
P reproduction outside the terms stated here should be sent to The Royal Society of
Chemistry at the address printed on this page.
Whilst this material has been produced with all due care, The Royal Society of Chemistry
cannot be held responsible or liable for its accuracy and completeness, nor for any
consequences arising from any errors or the use of the information contained in this
publication. The publication of advertisements does not constitute any endorsement by
The Royal Society of Chemistry or Authors of any products advertised. The views and
opinions advanced by contributors do not necessarily reflect those of The Royal Society of
Chemistry which shall not be liable for any resulting loss or damage arising as a result of
reliance upon this material.
The Royal Society of Chemistry is a charity, registered in England and Wales, Number
207890, and a company incorporated in England by Royal Charter (Registered No.
RC000524), registered office: Burlington House, Piccadilly, London W1J 0BA, UK,
Telephone: [phone].
For further information see our web site at www.rsc.org
Printed in the United Kingdom by CPI Group (UK) Ltd, Croydon, CR0 4YY, UK
7
0
0
P
F
5-
3
05 Foreword
1
0
8
8
7
1
8
7
9
9/
3
0
1
0.
1
oi: The reader holds a reference book in hand, published as a new addition to
g | d the Smart Materials series, which provides a great overview of recent prog-
or ress in this swiftly growing field in the form of chapters, written by well-
c.
s.rs known experts in their respective research areas. The volume is edited by
ub Professor Ali Eftekhari, a distinguished chemist and materials scientist, and
p
p:// a renowned expert in ionic liquids, nanotechnology, electrochemistry and
htt electroactive materials.
n
o In order to place the objectives of this monograph, let us first consider mol-
7
01 ten salts, low temperature ionic liquids (or “designer” media), and polymeric
2
er ionic liquids (as functional materials) as different laps in the knowledge and
b
m technology chain resulting in the current state-of-the-art of the subject dis-
e
ept cussed in this book. Ionic compounds that have a low melting point, such as
S
8 (the arbitrarily chosen) 100 °C, are usually classified as ionic liquids. When
on 1 compared with salts like NaCl (with a melting point of 801 °C) the distances
d
he between oppositely charged ions in the structure of ionic liquids is (substan-
s
bli tially) larger, the bonding coordination is poorer, and the charges are delo-
u
P calized. Due to this charge delocalization (in π-electron bonds) and to the
presence of at least one organic constituent, and related to conformational
freedom, the formation of stable crystal structures in ionic liquids is often
prevented. Fine-tuning of the chemical structure of the organic constituents
allows one to control the properties of ionic liquids, which endows these sys-
tems with a “designer” characteristic. The fine tuning of the structure, and
thus properties, provides engineered materials with controlled solubility,
dissolving characteristics, viscosity, vapor pressure, and electrical conductiv-
ity. Rapid growth of research into these low-melting point ionic liquids is also
related to their manifold applications as dispersing agents (solvents), elec-
trolytes, enhancing agents of chemical process efficiency and process safety,

Smart Materials No. 29
Polymerized Ionic Liquids
Edited by Ali Eftekhari
© The Royal Society of Chemistry 2018
Published by the Royal Society of Chemistry, www.rsc.org
vii
View Online
viii Foreword
and adhesive-sealant barriers, the latter being related to their low vapor pres-
sure. But reduced toxicity and non-flammability in combination with low
vapor pressure further enhance the scope of their applications, e.g. in green
chemistry. Although ionic liquids were first reported in 1914 by Walden, they
7
0 did not trigger substantial interest until recent decades. This is also due to
0
P
F quickly emerging applications, as processes that were feasible only at high
5-
53 temperatures have become now accessible due to the use of ionic liquids at
0
01 low temperatures opening new technologies in organic chemistry and energy-
8
78 related fields.
1
78 Naturally, the field of ionic liquids has been covered by some excellent
9
9/ reviews and books. As a great introduction, the volume published by the
3
10 Royal Society of Chemistry, authored by M. Freemantle, T. Welton, and R. D.
0.
1 Rogers, can be mentioned.1 An excellent review published in the scientific
doi: journal literature by Plechkova and Seddon2 provides great insights into
org | “Applications of ionic liquids in the chemical industry” from the historical
sc. beginnings to recent times.
bs.r Incorporation of polymerizable groups in the structures of the ionic liquid
u
p
p:// constituents yields polymerizable ionic liquids, which are the subject of a
htt very active area of contemporary materials research. The emergence of poly-
on meric ionic liquids – or poly(ionic liquid)s (PILs) – as functional materials has
7
1 opened novel applications in polymer electrolytes, dispersants and solvents,
0
2
er microporous membranes, green chemistry, and electroactive polymers. One
b
m of the early reviews by M. A. Firestone et al. still provides excellent insights
e
pt into the emergence of poly(ionic liquid)s.3
e
S
8 Of course, in physical chemistry of macromolecules, charged polyions
n 1 have been a subject of intensive research, not least due to the charged nature
o
ed of many biological macromolecules. One should however keep in mind that
h
blis in polyelectrolyte systems there is a dissolving liquid and counterions in a
u
P supporting electrolyte, thus the liquid phase is a solvent–ion-charged poly-
mer system. Strictly, for poly(ionic liquid)s no solvents are needed.
Swift progress in research and applications of poly(ionic liquid)s has more
than justified the publication of subsequent additional reviews, such as ref. 4
by M. Antonietti and colleagues.
In this present volume published by the Royal Society of Chemistry, the
fundamental concepts of and the basic differences between ionic liquids and
poly(ionic liquid)s, as well as detailed accounts on technological progress,
are provided in an excellently balanced fashion. Swift progress and growth of
interest, and the still relatively sparse book literature more than justify the
publication of the current volume edited by Professor Eftekhari. In this book,
in eighteen chapters, leading researchers give a comprehensive overview of
the state-of-the-art (and often even go “beyond the edge”) of the field.
The book begins with a great summary by J. Mays and co-authors discuss-
ing the use of ionic liquids as polymerization media in the “green synthe-
sis” of polymers. The advantages and the reduced environmental footprint
of the use of designer ionic liquids as solvents are presented. The second
chapter is also related to materials synthesis, but with a focus on porous,
View Online
Foreword ix
charged materials (with pore sizes across the length scales) using ionic and
poly(ionic) liquids. The authors, A. Dani, S. Bordiga et al., describe the fun-
damentals of using ionic liquid functionalities in the assembly, charging and
reorganization of functional materials, and making hybrid and responsive
7
0 functional materials. A nice section in this chapter discusses porosity evalua-
0
P
F tion approaches and contrasts micro-mesoporous structures. Olga Kuzmina
5-
53 in Chapter 3 very nicely describes cationic and anionic polyion-containing
0
01 poly(ionic liquid) structures, and provides very informative tables of the var-
8
78 ious poly(ionic liquid) cations–anions, the corresponding counterions, and
1
78 some material properties, like conductivity. The next section by H. Ohno and
9
9/ co-author draws the reader’s attention to stimulus responsive PILs, with a
3
10 focus on hydrophobic/hydrophilic transitions and the thermodynamic phase
0.
1 behavior of PIL–solvent systems. Structure–property relations and how these
oi:
d influence thermodynamic phases (including LCST-type phase transitions)
org | are explained. In the next chapter, Mikkola and co-authors continue the dis-
sc. cussion on responsive behavior, in particular regarding polarity-switchable
bs.r media of molecular liquids. Such systems possess great promise in designer
u
p
p:// chemical transformations. Still along the highly promising line of research
htt with a focus on electro-responsive fluids with charged constituents, Jianbo
on Yin and co-workers provide a very nice section introducing the principles
7
1 and the potential applications of PILs as novel fluidic systems in electrorhe-
0
2
er ology, including molecularly aligned anisotropic fluids. Chapter 7 provides
b
m a discussion on preparing nanogels from PILs, authored by Y. B. Xiong et al.
e
pt A facile one-step cross-linking copolymerization is used here to obtain thermo-
e
S
8 and multiple-responsive nanogels with potential use e.g. in the capture and
n 1 release of molecular cargos. The next section by H. Randriamahazaka and
o
ed co-authors takes the reader beyond the more conventional stimuli and offers
h
blis a discussion on redox-active PIL functional systems. Regarding applications,
u
P employing a redox trigger opens the range of uses encompassing devices
with electrochemical switching, supercapacitors, electrolytes for use in bat-
teries, fuel cells, sensors, and actuators. Next, H. Lin and co-workers focus
on “doping” of polymers with PILs for morphology control to regulate e.g.
gas separation of membranes, while Y. J. Li and co-author in the subsequent
chapter show how polymer/IL “composites” can be used to tailor anti-static
and dielectric performance. Ionogels and hydrogels have gained widespread
use as biomaterials. In the next Section S. S. Silva and R. L. Reis focus on
polymeric hydrogels processed in ionic liquids, and provide examples of bio-
materials obtained via this route. Regarding biomaterials, Kadokawa then
shows how the functionality of polysaccharides can be enhanced by ionic
liquids. In this part, the particularly important use of ionic liquids to dis-
solve polymers, including cellulose and chitin that cannot be dissolved, or
are notoriously difficult to dissolve in other solvents, is nicely documented.
Torresi et al. return, in their contribution, to the added versatility regard-
ing the functionality of ionic liquids and PILs, with a particular focus on
electrochromic and gas storage applications. Zopf et al. in Chapter 14 show
an exciting idea of how ionic liquid gels can be made and used as wearable
View Online
x Foreword
electrochemical storage devices, such as batteries and supercapacitors. Next,
McIntosh and co-authors also focus on wearable devices, but the application
in their case is related to sensors. Here, ionic liquids provide enhanced ana-
lyte sensing specificity, and sensor performance improvement. They point
7
0 out that although a large number of ionic liquids have been explored, there
0
P
F is still a lot of space for further research into task-specific selection of ionic
5-
53 liquids for particular use in designer sensors. Chapter 16 then provides an
0
01 overview of ionic gels, electrochemical ionic actuators, ionic metal–polymer
8
78 composites, and related responsive materials, authored by A. Maziz, C. Bergaud
1
78 and co-worker. The focus here is primarily on mechanical actuation. The
9
9/ penultimate chapter shows yet another exciting application area of using
3
10 PILs to capture CO , which is a very important focus field in combatting
0. 2
1 climate change. Finally, the last contribution written by C. P. Lee and K. C. Ho
oi:
d introduces the reader to the highly interesting potential application of PILs
org | as electrolytes in dye-sensitized solar cells. This contribution also offers a
sc. good general introduction to employing solar radiation as a sustainable
bs.r source of energy.
u
p
p:// The unique collection of chapters in this book, showing the state-of-the-
htt art, from the basics, via sketching the new trends, to introducing emerging
on possibilities of ionic liquids in combination with polymers, or of poly(ionic
7
1 liquid)s, with a very strong focus on responsive materials, is a very essential
0
2
er read for chemists, materials scientists, physicists and engineers.
b
m
e G. J. Vancso
pt
e
S
8
on 1 References
d
e
h
blis 1. M. Freemantle, T. Welton and R. D. Rogers, An Introduction to Ionic Liquids,
Pu RSC Publishing, 2009, ISBN-13: 978–1847551610.
2. N. V. Plechkova and K. R. Seddon, Applications of ionic liquids in the
chemical industry, Chem. Soc. Rev., 2008, 37(1), 123–150.
3. O. Green, S. Grubjesic, S. Lee and M. A. Firestone, The design of polymeric
ionic liquids for the preparation of functional materials, Polym. Rev., 2009,
49(4), 339–360.
4. J. Yuan, D. Mecerreyes and M. Antonietti, Poly(ionic liquid)s: An Update,
Prog. Polym. Sci., 2013, 38(7), 1009–1036.