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Supramolecular Gels
Supramolecular Gels
Edited by
Tifeng Jiao
Editor All books published by WILEY-VCH
are carefully produced. Neverthe-
Prof. Tifeng Jiao less, authors, editors, and publisher
Yanshan University do not warrant the information con-
School of Environmental and Chemical tained in these books, including this
Engineering book, to be free of errors. Readers are
No. 438 West Hebei Street advised to keep in mind that state-
Qinhuangdao ments, data, illustrations, procedural
066004 Hebei Province details, or other items may inadver-
China tently be inaccurate.
10 9 8 7 6 5 4 3 2 1
v
Contents
Preface ix
Index 257
ix
Preface
Leng review the recent advances for the synthesis of hydrogels and aerogels from
cellulose and chitin and their application for water remediation. Fabrication and
functionalization of biobased aerogels and their performance for oil remediation
are summarized by He et al. Finally, Xue Jin and Pengfei Duan highlight and put
into perspective a few recent advances in the field of luminescent gels.
I would like to greatly thank all these colleagues for providing these deep and
illustrative insights into their work and that of their peers. I believe that the content
of supramolecular gels presented in this book can provide readers with guidance on
fundamental understanding of supramolecular gels and promote the development
of supramolecular gels.
1
1.1 Introduction
Since the 1990s, substantive development has been achieved in research related
to molecular gels [1, 2]. Thousands of molecular gelators have been reported [2].
Meanwhile, with rapid development in supramolecular chemistry and nanoscience,
in-depth understanding has been gained and many new research branches have
emerged [3, 4]. By combining research results and theoretical calculations, theories
in molecular gel study have been built. Preparation of molecular gel has also been
gradually changed from the accidental discovery stage to the aimed designed stage.
A typical characteristic of research on molecular gels is the interdisciplinary feature.
Generally, research on molecular gels includes knowledge related to soft matter,
self-assembly, rheology, thermodynamics, chemical synthesis, theoretical calcula-
tion, simulation, etc. Macroscopically, molecular gels are solid-like. Microscopically,
molecular gels are made up of non-covalent interaction-based network structures
consisting of a small quantity of molecular gelators and abundance of solvents [5].
The solvent molecules are trapped in the network structure via capillarity, surface
tension, and other immobilization forces. Thus, molecular gels possess typical
microheterogeneous structure. Different from chemical gels and polymer gels,
non-covalent bonding-based network endows molecular gels prominent thermal
reversibility, shear thixotropy, and stimulus response [6, 7]. These properties lay
solid foundation for further application of the molecular gels. However, pronounced
application of molecular gel has not been realized.
Stability is an important factor that affects the practical applications of molecular
gels [8]. This is because, the formation and existence of a molecular gel is based on
an equilibrium of dissolve-aggregation, which is based on a variety of non-covalent
interactions [7]. The equilibrium may be broken by any tiny external disturbance,
causing melting of phase transition in the molecular gel. In order to get stable molec-
ular gels, it is necessary to strengthen the factors that are helpful to maintain the
dissolve-aggregation balance. For example, high-boiling point liquids are used to
Supramolecular Gels: Materials and Emerging Applications, First Edition. Edited by Tifeng Jiao.
© 2021 WILEY-VCH GmbH. Published 2021 by WILEY-VCH GmbH.
2 1 Molecular Gel as Medium or Intermediate in Functional Materials Synthesis
prevent gel-sol phase transitions caused by solvent volatilization [9]. Thermal insu-
lation and vibration reduction are realized through packaging, so as to overcome the
gel damage caused by vibration and heat. In fact, it is in this way that the intelligent
propellant based on molecular gel is prepared.
Another way to promote the practical application of molecular gels is to use them
as an intermediate to construct special materials with special structures and excel-
lent properties, where the application of molecular gels will be highlighted [10, 11].
Based on this consideration, efforts have been devoted to the study of molecular gels
as intermediates in functional materials fabrication (Scheme 1.1), such as in fluores-
cent sensing film, gel emulsions, and low-density porous materials. With molecular
gel strategy, a series of materials with favorable performance have been obtained. In
this chapter, the application of molecular gel strategy in the preparation of fluores-
cence sensing thin film materials and low-density porous materials is described in
combination with laboratory practice. On this basis, the main challenges of related
research are proposed, and the prospect and development trend of molecular gel
expansion research are prospected.
Scheme 1.1 Molecular gel strategy in fabrication of fluorescent sensing film and gel
emulsion as well as porous materials.
Figure 1.1 Illustration of the molecular gel for fluorescent film fabrication.
As known, solvent is the main component (more than 90%) in a molecular gel
and the self-assembled supramolecular gel network accounts for only ∼2%. Thus,
the corresponding xerogel obtained from removing the solvent possesses features
of porous network structure, which is beneficial for fluorescent sensing because of
the permeability at the molecular level. Preferable permeability will lay a founda-
tion for fast and effective interaction between the analyte and the sensing units and,
therefore, result in improved sensing performance, such as fast response and high
reversibility and sensitivity. In addition, shear thixotropy of some molecular gels
would facilitate sensing film preparation, as they can be easily sprayed or spin coated
onto the solid substrate to form porous films. Accordingly, molecular gel strategy
has been developed to fabricate different types of fluorescent sensing films [17–19].
Details of the strategy are illustrated in Figure 1.1. In the strategy, fluorescent unit is
introduced to the molecular design of a gelator and the achieved fluorescent molec-
ular gels are used to construct sensing film with porous network microstructure.
With the method, fluorescent films with favorable sensing performance for volatile
organic compounds (VOCs), narcotics, and chemical agent have been realized and
some of the sensing films have been made into devices for real-life applications.
state [23]. After more than 20 years of development, abundance of gelator units have
been reported, including cholesterol and its derivatives, alkanes, amino acids, and
aromatic compounds. [1]. Rational combination of a fluorophore and the gelator
units will enable the access of favorable fluorescent molecular gelator, which lay
solid foundation for fluorescent sensing film fabrication.
Scheme 1.2 Structure design for gelator molecules used for fluorescent film fabrication.
In Sections 1.2.2 and 1.2.3, fluorescent gelators with different molecular struc-
tures will be introduced. Based on systematic study of the self-assembly feature,
gelation behavior as well as rheological properties of the gelators, fluorescent films
will be obtained via techniques of drop casting or spray coating. When gelating sol-
vent is removed, porous sensing films can be achieved. Meanwhile, porosity and
microstructure of the film can be adjusted by varying the concentration of the gela-
tor, gelating solvent, or the drying process. On that basis, the photophysical behavior
and sensing performance of the films will evaluated. Furthermore, films with out-
standing sensing performance will be selected to make sensor device. The molecular
gel strategy will not only broaden the application of molecular gel, but also provide
convenience for sensor development.
O
O
N O n O
H
N O
O
N O
O
H
O n O N
O
Compound 1: n=2 O
Compound 2: n=11
O
O
N N O
H
O S O
O N
N O S
O O
O N H
N
O
Compound 3 O
O
N
O O
NH
O
HN
O
O
N Compound 4
A series of molecular systems (compounds 1∼4) for organic amine sensing has
been achieved by the combination of the two units (Scheme 1.3) [29–32]. The four
compounds show varied assembly behavior in different solvents and it was found
that sensing performance of the system was highly dependent on the assembled
structure of the molecules. The molecular gel-based film was obviously superior to
the film obtained by simple casting of the compounds. Sensing films obtained from
molecular gel strategy show features of porous network structure: film 1 is made
up of nanofibers of ∼80 nm [29]; film 2 is characterized by stacking of nanopar-
ticles of ∼150 nm (Figure 1.2a) [30]; film 3 contains abundance of nanofibers of
∼100 nm (Figure 1.2b) [31]; morphology of film 4 is similar to that of film 3 except
for the smaller size of nanofibers [32]. The four films exhibited different sensing
2 μm 5 μm
(a) (b)
Figure 1.2 Self-assembled structures of compound 2(a) and 3(b). (a and b) SEM images of
film 2 and 3 through the assembly of compound 2 and 3, respectively. Source: Adapted with
permission from He et al. [31] and Shang et al. [32]. © 2016 Elsevier.
6 1 Molecular Gel as Medium or Intermediate in Functional Materials Synthesis
Blank
8 After 50 s MPEA vapor
8 1.0
6 6 91.6% 0.8
4
0.6
4 2
0 0.4
2 600 650 700 750 800
Wavelength (nm) 0.2
Film treated with MPEA saturated vapor
0 0 2 4 6 8 10 12
0 10 20 30 40 50 Cycle number
(c) Time (s) (d)
Figure 1.3 Sensing performance of some typical fluorescent films based on molecular gel
strategy. (a) Fluorescence response of film 2 to a series of volatile compounds; (b)
fluorescence response of film 3 to aniline; (c) fluorescence response of film 3 to
N-methyl-phenethylamine (MEPA); (c) reversible sensing response of film 2 to MEPA vapor;
inset shows the fluorescence images of the film before (up) and after (down) exposure to
MEPA vapor; (d) reversible fluorescence response of film 2 to MEPA vapor. Source: He et al.
[31] /Elsevier.
and the corresponding films show different sensing performance. The film made up
of uniform nanofibers was proved to be sufficient in aniline sensing with response
less than 1 s and a detection limit of 12.7 mg m−3 ppm.
O
N O
O H O O
N O
O N
O O H O
O N
O
Compound 5
*O
O2N NH O
N N H2C
O
Scheme 1.5 Structure of the typically designed molecular gelator, compound 6. Source:
Based on Yu et al. [34].
8 1 Molecular Gel as Medium or Intermediate in Functional Materials Synthesis
Methanol I S n-Hexane I I
Ethanol I G n-Heptane I I
n-Propanol I G n-Octane I I
n-Butanol I G n-Nonane I I
n-Pentanol I G n-Decane I I
n-Hexanol I P Cyclohexane I I
n-Heptanol I P Acetonitrile I G
n-Octanol I P Water I I
n-Nonanol I I DMF S P
n-Decanol I I DMSO I G
Acetone S P Acetic acid I I
Benzene S S Ethyl ether I I
Toluene S S Ethyl acetate S S
THF S S Dichloromethane S S
Pyridine S S Trichloromethane S S
HO
OH
O O OH
O
HO
NH
H
H
O
H
O 8O
H 8 O
HN
OH
HO O O
HO
OH
Scheme 1.6 Molecular structure of compound 7. Source: Based on Sun et al. [35].
Because of their advantages at low density, high porosity, large surface area, and
tunable pore size, porous materials are playing increasingly important roles in
many fields, such as separation, catalysis, molecular recognition, bioengineering,
and environmental science [39, 40]. A key point in porous materials preparation
is to control the pores, including pore size, pore shape, and pore distribution.
Commonly used methods for porous materials preparation includes gas foaming,
10 1 Molecular Gel as Medium or Intermediate in Functional Materials Synthesis
O H 4 H O
O N N O
O O
CH3 CH3
Compound 8
Molecular structures of some typical molecular gelators that can serve as stabiliz-
ers in gel emulsions formation are shown in Scheme 1.8. As an example, a series of
gel emulsions of W/O type can be obtained when either of the gelators is used as a
12 1 Molecular Gel as Medium or Intermediate in Functional Materials Synthesis
stabilizer and tert-butyl methacrylate is used as the continuous phase [47]. Polymeric
porous materials with varied internal structure as well as mechanical properties can
be achieved by polymerization of the different gel emulsions (Figure 1.5) [48]. The
porous materials show high performance in absorption of organic liquids. Mean-
while, the absorbed solvents can be easily recovered by a squeezing process. In this
way, the porous materials can be recycled and the absorption process can be repeated
for more than 10 times. Except for optimization on the water content in the gel
emulsion, properties as well absorption behavior of the porous material can also
be enhanced by the introduction of some typical additives. For example, introduc-
ing some reactive silyl reagents is helpful to improve the mechanical strength and
absorption capacity of the porous materials.
O H O
H
O N N
N O
O O
Compound 9 NH
O
Fe
O O
H
OH N
HO O
O O CH2
N
O
OH
Compound 10 Compound 11
Scheme 1.8 Molecular structure of the gelators (compound 9–11) stabilizer used for gel
emulsion and porous materials preparation.
Compound 10, which is a typical cholesterol gelator with two hydroxyl groups in
the structure, can also serve as a stabilizer for W/O gel emulsions [49]. Using styrene
as the continuous phase and water as the dispersed phase, a series of gel emul-
sions with outstanding stability can be prepared. After polymerization and drying,
corresponding porous polystyrene materials were synthesized. Density of the mate-
rials can be adjusted by the variation of water content in the gel emulsions and
polystyrene materials with ultralow density was presented. The preparation can be
processed under mild conditions, where no complex or high energy cost drying pro-
cess is needed. No high-cost post-treatment is needed as the water in the polymer-
ized materials can be removed by squeezing and simple drying at 50 ∘ C. The porous
polystyrene materials can be used to remove some organic liquids from water. The
materials can be recycled by subsequent squeeze, washing with ethanol, and drying
steps (Figure 1.6) [50].
Another representative molecular gelator stabilizer contains a phenylalanine
group as a linker, and a carboxyl group in a cholesterol derivative (compound 11)
[51]. With the stabilizer, gel emulsion with tunable rheological properties can be
1.3 Molecular Gel as Intermediate in Synthesizing Porous Materials 13
(a)
(b) 105
(c)
4
10
103 50
0.18 500
1000
102
G′ (Pa)
2000
0.16 3000
tgδ =G″/G′
4000
0.14 200 μm
101
50
0.12 (d)
500
100 1000
0.10
2000
10–1 0.08 3000
0 1000 2000 3000 4000
Water content (μl) 4000
10–2
10–1 100 101 102 103
200 μm
Stress (Pa)
Figure 1.5 Typical gel emulsions and porous materials prepared by using molecular
gelator as stabilizer. (a) Photos of the styrene gel. Photos of gel emulsion with different
amounts of stabilizer. (b) Rheological behaviors of gel emulsions with different water
contents. (c and d) SEM images of porous materials prepared from gel emulsions with
different amounts of n-heptane as additives.
35
Toluene
Phenol
30
15
10
0
(a) Solvents
23 mm 24 mm
24 mm 2. Dry up
Step 1
(b)
Compound 12
O
H
O N
4 N
H
O
Compound 13
H
O N O
O O
O N
H
gels) show different response to external stimulus. For example, networks in both
types of the gels can be broken under vigorous shearing, such as stirring, pumping,
or shaking, which may result in phase separation or phase transition of the gel. It is
hardly for the chemical gels to be recovered after the disruption, as the chemically
bonded network is reversibly broken. But many molecular gels can be recovered
when the shearing is removed. The preferable stimulus-responsive characteristics
of molecular gels endow them great potential in applications of template synthesis,
controlled release, tissue culturing, separation, information storage, sensing, etc.
Moreover, the concentration of a gelator is usually very low in a molecular gel,
which is a big advantage for further applications in molecular recognition, template
synthesis, and synthetic intermediate. Introducing the molecular gel strategy to
synthesize high-performance fluorescent sensing film and low-density porous mate-
rials shows some preliminary application of molecular gel in synthetic intermediate.
It is expected that molecular gels will play more important roles in the research area
of synthetic medium, which may include innovation in liquid–liquid extraction,
cultivation of high-quality crystals, stabilization of solid–liquid suspension system
extraction technology.
In addition, there are problems to be solved when molecular gel strategy is used
in the synthesis of fluorescent sensing films and low-density porous materials.
For example, adhesion of some fluorescent films obtained from molecular gel
needs to be improved. Effect of molecular structure of the gelator stabilizer on
the properties of the gel emulsions as well as the low-density porous materi-
als needs to be given more attention. This will pave way for achieving porous
materials with excellent mechanical strength and tunable internal microstruc-
ture.
16 1 Molecular Gel as Medium or Intermediate in Functional Materials Synthesis
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status of the field, and where is it going? J. Am. Chem. Soc. 136: 7519–7530.
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Faire parler des subalternes, des domestiques, le comte même
ne l’eût pas fait. La comtesse n’y pouvait songer. Des personnes
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tenu d’une longue main amaigrie, pâle et finement révélatrice de la
race, avait surpris bien des négligences vilaines, au coin des tapis
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personne, un peu triste, parfaitement correcte, belle à souhait,
tournant vers ceux qui lui adressaient la parole le plus pur regard du
monde…
Marie, décidément, avait adopté la coiffure à la Rossetti.
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ses yeux. Elle ôtait ainsi à sa physionomie l’excès d’étrangeté qui,
bon pour séduire les hommes, pouvait paraître suspect à la vieille
dame.
— Eh bien, ma mère ?
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— Si, un peu. Annette cessa de sourire.
— Il faut la rendre bien heureuse, n’est-ce pas, petite sœur, bien
heureuse, jusqu’à la fin. Tu ne peux pas comprendre ça, toi, avec
tes dix-sept ans, mais c’est triste, vois-tu, de se voir vieillir. Notre
mère en souffre, parfois.
— Oh !… Crois-tu ?
— Écoute : l’autre jour, nous causions : « Je faiblis, me dit-elle, je
m’en vais, mon fils ! » — « Et moi maman, lui dis-je, à mesure que
vous vieillirez, je sens que je vous aimerai toujours mieux. » — Sais-
tu ce qu’elle m’a répondu ? — « Oh, alors, mon cher petit, comme il
va me devenir doux de vieillir ! »
Les deux enfants se regardèrent furtivement, à cause des larmes
qui gonflaient leurs yeux…
DEUXIÈME PARTIE