A dimethoxypillar[5]arene/azastilbene host-guest recognition motif and its applications in the fabrication of polypseudorotaxanes

Article abstract of DOI:10.1039/c9ob00862d

Pillar[n]arenes, known as the fifth generation of host macrocycles since 2008, have become a popular topic over the past ten years. Until now, the studies of pillar[n]arenes were mainly focused on pillar[5]arenes owing to their easy synthesis and high yields. In particular, 1,4-dimethoxypillar[5]arene (DMP5), which shows a simple structure, efficient synthesis and high yield, has played important roles in the construction of various advanced supramolecular architectures. However, DMP5 has only displayed host-guest binding properties towards some guests. Therefore, the investigation of the host-guest chemistry of DMP5 should be able to greatly promote the development of pillararene chemistry. Herein, a photosensitive azastilbene derivative was chosen as a neutral guest to study the host-guest binding and stimuli-responsive behavior with DMP5. In addition, the binding behavior of DMP5 towards a series of analogous neutral guest molecules was investigated to study the driving forces of the host-guest interaction between DMP5 and the azastilbene guest. Moreover, the [2]pseudorotaxane based on DMP5 and the azastilbene guest was used to construct a polypseudorotaxane via metal coordination.

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A dimethoxypillar[5]arene/azastilbene host–guest recognition motif and
its application in the fabrication of polypseudorotaxane
ab
a
a
a
ab
c
Liyun Wang , Danyu Xia* , Jianbin Chao , Junjie Zhang , Xuehong Wei* and Pi Wang*
Received (in XXX, XXX) Xth XXXXXXXXX 20XX, Accepted Xth XXXXXXXXX 20XX
5
DOI: 10.1039/c0xx00000x
Pillar[n]arenes, known as the fifth generation of host macrocycles since 2008, have become a
popular topic over the past ten years. Until now, the studies of pillar[n]arenes have been mainly
focused on pillar[5]arenes owing to their easy synthesis and high yields. Especially, 1,4-
dimethoxypillar[5]arene (DMP5), which shows simple structure, efficient synthesis and high yield,
has played important roles in the construction of various advanced supramolecular architechtures.
However, DMP5 has only displayed host−guest binding property towards some guests. Therefore,
the investigation of the host−guest chemistry of DMP5 should be able to greatly promote the
development of pillararene chemistry. Herein, a photo-sensitive azastilbene derivative was chosen
as a neutral guest to study the host−guest binding and stimuli-responsive behavior with DMP5. In
addition, the binding behavior of DMP5 towards a series of analogous neutral guest molecules were
investigated to study the driving forces of the host−guest interaction between DMP5 and the
azastilbene guest. Moreover, the [2]pseudorotaxane based on DMP5 and the azastilbene guest was
used to construct a polypseudorotaxane via metal coordination.
1
0
1
5
1
. Introduction
Stoddart et al. reported the host–guest interaction between
DMP5 and 1,8-diaminooctane;36 Huang et al. reported the
host–guest interaction bewteen DMP5 and n-octylethyl
20
25
30
35
40
Supramolecular chemistry, which plays a major role in the
45
50
55
60
65
development of chemistry, has experienced remarkable
3
7
ammonium hexafluorophosphate; Li et al. reported some
neutral guests that can complex with DMP5, which are 1,4-
dibromobutane,38 1,4-dicyanobutane,39 1,4-[1,2,4]triazol-1-yl-
butane40 and [1,2,3]triazol-1-yl-4-cyanno-butane;12 Ogoshi et
al. reported the complexation between DMP5 and N-alkyl-
pyridine bromide.41 These DMP5-based host−guest systems
played important roles in the construction of various advanced
supramolecular architechtures, such as threaded structures,
1
-4
progress over the last five decades. Macrocycles are the
basic building blocks to construct various supramolecular
architectures and materials due to their special excellent
hostguest properties.5-11 Therefore, the exploration of new
macrocycles and their host−guest recognition is an important
and essential part in supramolecular chemistry.12-14
Pillar[n]arenes,15,16 known as the fifth generation of host
macrocycles, have become a popular topic over the past ten
years.17 Due to their distinct rigid and pillar structures,
electron-donating cavities, and easy functionalization,
pillararenes have displayed excellent host–guest recognition
properties with diversiform guest molecules, setting a stage
for the fabrication of various interesting supramolecular
systems in the application of many fields.18-35
Until now, the studies of pillar[n]arenes have been mainly
focused on pillar[5]arenes owing to their easy synthesis and
high yields. The host–guest chemistry of pillar[5]arenes has
been widely explored. However, among diverse pillar[5]arene
derivatives, 1,4-dimethoxypillar[5]arene (DMP5), which
shows the highest yield until now, has only displayed host–
guest binding property towards some guests. For instance,
supramolecular
systems.1
polymers
and
stimuli-responsive
2,29,41-45
It can be seen that neutral DMP5 can
complex with cationic and neutral guests due to its electron-
rich cavity. Between them, neutral guests are more
advantageous because of their relatively higher solubility in
nonpolar solvents than cationic guests which is the same as
DMP5. Therefore, the study of DMP5-based host−guest
reconition property with neutral guests will facilitate its
further application in the construction of advanced
supramolecular systems. Furthermore, introducing stimuli-
responsiveness to host–guest systems are of great importance
for the construction of functional supramolecular structures,
such as molecular machine, stimuli-responsive self-assemblies
and adaptive materials.46-48 Herein,
a
photo-sensitive
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azastilbene derivative, trans-4,4′-vinylenedipyridine (trans-G1),
3. Results and discussion
was chosen as a neutral guest to study the host–guest binding
behavior and stimuli-responsive complexation with DMP5. In
addition, the binding behavior of DMP5 towards a series of
analogous neutral guest molecules, 4,4′-ethylenedipyridine
1
First, H NMR spectroscopy was used to study the host–guest
complexation behaviour between DMP5 and these neutral guests,
trans-G1, G2, G3, G4, G5 and G6. As shown in Fig. 1, the host–
guest interaction between DMP5 and trans-G1 was clearly
35
40
45
50
55
60
5
(G2), trans-4-styrylpyridine (G3), 4,4′-bipyridine (G4), trans-
observed. The peaks related to the protons H
trans-G1 shifted upfield and peaks related to H
a
, H
b
and H
c
on
stilbene (G5) and trans-3-hexene (G6), were investigated to
study the driving forces of the host–guest interaction between
DMP5 and trans-G1. Moreover, the [2]pseudorotaxane
formed by DMP5 and trans-G1 was used to construct a
polypseudorotaxane via metal coordination (Scheme 1).
b
and H
c
became
broad of the equimolar mixture of DMP5 and trans-G1
compared to trans-G1 alone. The remarkable changes of the
signals for trans-G1 resulted from the formation of a threaded
structure DMP5trans-G1, and shielded by the electron-rich
cyclic structure of DMP5. Moreover, the broadening effect of the
signals was due to complexation dynamics.39 In addition, a 2D
NOESY NMR experiment was employed to study the relative
positions of the components in DMP5trans-G1 (Fig. S1). NOE
correlation signals were observed between proton H
and protons H of DMP5 (Fig. S1, A), between proton H
trans-G1 and protons H and H of DMP5 (Fig. S1, B and C),
and between proton H of trans-G1 and proton H of DMP5 (Fig.
1
0
a
of trans-G1
3
b
of
1
3
c
3
S1, D). These results provided convincing proof for the formation
of a [2]pseudorotaxane between DMP5 and trans-G1. Moreover,
the stoichiometry and association constant between DMP5 and
1
trans-G1 were investigated by H NMR titration experiments.
The titration experiments were carried out with solutions which
had a constant concentration of trans-G1 (1.00 mM) and different
concentrations of DMP5 (Fig. S2). By a mole ratio plot and a
non-linear curve-fitting method, the stoichiometry and
association constant between DMP5 and trans-G1 were
2
−1
calculated to be 1:1 (Fig. S3) and (4.45 ± 0.23) × 10 M (Fig.
S4), respectively.
Scheme 1. (a) Chemical structures of compounds DMP5, trans-G1, G2,
G3, G4, G5 and G6; (b) cartoon representation of the photo-responsive
host−guest recognition between DMP5 and trans-G1 and the Cu(II)
linked polypseudorotaxane.
1
5
2
. Experimental section
All reagents were commercially available and used as
20
25
30
supplied without further purification. Solvents were either
employed as purchased or dried according to procedures
described in the literature. DMP5 was prepared according to
1
Fig. 1 Partial H NMR spectra (600 MHz, CDCl , room temperature): (a)
3
published procedures.15 Compounds trans-G1, G2, G3, G4, 65 DMP5 (5.00 mM); (b) trans-G1 (5.00 mM) and DMP5 (5.00 mM); (c)
2
G5, G6 and Cu(OAc) were commercially available. NMR
trans-G1 (5.00 mM).
spectra were recorded with a Bruker Avance DMX 600
spectrophotometer. FT-IR spectra were recorded with a
Thermo Scientific Nicolet iS50 instrument. XRD were
performed with a Bruker D2 PHASER. Scanning electron
microscopy investigations were carried out on a TASCAN
(LYRA3) instrument. Atomic force microscopy experiments
were performed by a Bruker Multi-Mode 8.0 instrument.
Similarly, the host–guest complexation behaviour between
DMP5 and G2 was also studied by H NMR spectroscopy. As
shown in Fig. S5, significant chemical shift changes of the signals
for the protons on G2 appeared upon the addition of DMP5. The
peaks related to Ha′, Hb′ and Hc′ shifted upfield and became broad.
Meanwhile, NOE correlation signals were observed between
1
7
0
proton Ha′ of G2 and protons H
1 2 3
, H and H of DMP5 (Fig. S6, A,
2
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B and C). These results suggested the host−guest complexation 45 DMP5trans-G1 with UV light at 365 nm, the peaks related to
between DMP5 and G2. In addition, 1H NMR titration
experiments were carried out to determine stoichiometry and
association constant between DMP5 and G2 (Fig. S7), which
H
H
, H
a
b c
and H on trans-G1 weakened and the signals for protons
a*, Hb* and Hc* on free cis-G1 were clearly observed (Fig. 2c
and 2d), suggesting that the host–guest interactions between
DMP5 and trans-G1 were destroyed and there was no
2
−1
5
were calculated to be 1:1 (Fig. S8) and (4.55 ± 0.31) × 10 M
(
Fig. S9), respectively. Next, the host–guest complexation 50 complexation between DMP5 and cis-G1. The reason is that the
properties of DMP5 towards G3, G4, G5 and G6 were studied.
From the H NMR spectroscopy data, it can be seen that there
size of cis-G1 is larger than the cavity of DMP5.50
1
In addition, the [2]pseudorotaxane formed by DMP5 and
trans-G1 was used to fabricate a polypseudorotaxane linked by
were no chemical shift changes or broadening phenomena of the
peaks related to the protons on these neutral guests or DMP5 of
their equimolar mixtures compared to DMP5 and these guests
alone, indicating that there were no host–guest interactions
between DMP5 and these guest molecules (Fig. S10, S11, S12
and S13).
From the host−guest complexation behaviour of DMP5 to
trans-G1, G2, G3, G4, G5 and G6, it can be seen that only trans-
G1 and G2 which possess two pyridyl groups which are not
directly linked can complex with DMP5. That is to say electron-
deficient pyridyl group and the linker between the pyridyl groups
are the key parts in the formation of the [2]pseudorotaxanes,
DMP5trans-G1 and DMP5G2.49 The reason may be that the
C–H···N or C–H···O hydrogen-bonding interactions and C–H··π
interactions play important roles in the threaded structure since
the pyridyl groups of trans-G1 and G2 located at the rim of the
cavity of DMP5. Therefore, multiple weak C–H···N interactions
between the methyl groups on DMP5 and the nitrogen atoms of
the pyridyl groups on trans-G1 and G2 are the dominant driving
forces for complexation.40
10
15
20
25
Cu(OAc)2 (Cu(II)) coordination. As
a
comparison, the
55
60
65
coordination between Cu(II) and trans-G1 was investigated. As
shown in Fig. 3a and 3b, upon addition of Cu(II) to the solution
of trans-G1, the peaks related to H and H shifted downfield and
a b
all of the peaks became broad, indicating the formation of
coordination polymer based on trans-G1. Meanwhile, upon
addition of Cu(II) to the solution of DMP5 + trans-G1, the peaks
a b
related to complexed H and H shifted downfield and all of the
peaks became broad (Fig. 3c and 3d), suggesting the formation of
the metallosupramolecular polypseudorotaxane based on
DMP5trans-G1. The result was then confirmed by 2D DOSY
NMR spectroscopy experiments. As shown in Fig. 4 and Fig. S14,
compared with the equimolar mixture of DMP5 + trans-G1
solution, the diffusion coefficient (D) decreased from 2.24 × 10‒9
to 1.00 × 10‒9 m2s‒1 upon addition of Cu(II), indicating the
formation of the polypseudorotaxane.
7
0
1
Fig. 3 Partial H NMR spectra (600 MHz, CDCl
3
, room temperature): (a)
trans-G1 (5.00 mM); (b) after addition of equimolar Cu(II) to a; (c)
DMP5 + trans-G1 (5.00 mM); (d) after addition of equimolar Cu(II) to c.
3
0
1
Fig. 2 Partial H NMR spectra (600 MHz, CDCl
3
, room temperature):
(
a) trans-G1 (5.00 mM); (b) trans-G1 (5.00 mM) after irradiation
with UV light at 365 nm; (c) DMP5trans-G1 (5.00 mM); (e) DMP5
+
trans-G1 (5.00 mM) after irradiation with UV light at 365 nm.
Next, the photo-responsive property of the host−guest
3
5
complexation between DMP5 and trans-G1 which introduced by
photo-sensitive property of trans-G1 was investigated via 1
NMR spectroscopy. As shown in Fig. 2a and 2b, the peaks related
to the protons H , H and H of trans-G1 weakened accompanied 75 Fig. 4 Diffusion coefficient D (600 MHz, CDCl , room temperature) of
H
a
b
c
3
4
0
by the enhancement of the peaks related to the protons Ha*, Hb*
and Hc* of cis-G1 upon irradiation by UV light at 365 nm,
indicating that trans-G1 photoisomerized from the trans state to
the cis state and the trans–cis conversion was 65% at a
photostationary state. In addition, after irradiating a solution of
DMP5 + trans-G1 (5.00 mM) and after addition of equimolar Cu(II).
FT-IR spectroscopy was performed to investigate the solid
structure of the polypseudorotaxane. As shown in Fig. S15, the
main peaks related to DMP5 + trans-G1, the polypseudorotaxane
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and Cu(II) were marked and assigned. The polypseudorotaxane 50 polypseudorotaxane by Cu(II) coordination. This host–guest
showed strong absorbance bands including =C−H, C–H, C=C and
C=N of the stretching vibrations at 2949, 2827, 1599 and 1598
recognition system based on DMP5 and the neutral guest can be
used as a new building block to fabricate supramolecular
architechtures which can be applied in various fields such as
sensors, supramolecular polymers and molecular machines.
cm−1 and –−CH
2
− or −CH3, C−O−C and =C−H of the bending
vibration at 1448−1384, 1206 and 1041 cm−1
,
respectively. In
5
0
5
0
addition, these adsorption bands became broad compared to the
mixture of DMP5 and trans-G1. The powder X-ray diffraction
spectrum (XRD) experiment was also carried out to investigate
the solid state of the polypseudorotaxanes. As shown in Fig. S16,
broad peaks appeared on the spectrum of the polypseudorotaxane,
indicating that it was an amorphous material.51 Scanning electron
microscopy (SEM) were further utilized to investigate the
5
5
Acknowlegment
This work was supported by the National Science
Foundation for Young Scientists of China (Grant 21704073)
and the Natural Science Foundation for Young Scientists of
Shanxi Province, China (Grant 201801D221078).
1
1
2
micromorphology of the polypseudorotaxane. As shown in Fig. 60 Notes and references
5
a, a rod-like fiber with the diameter about 5 μm were observed
aScientific Instrument Center, Shanxi University, Taiyuan, 030006, P. R.
China; E-mail: danyuxia@sxu.edu.cn
obtained from high concentration solution of the
a
b
polypseudorotaxane. In addition, as shown in Fig. 5b, the solid
state of the polypseudorotaxane showed connected structures.
Atomic Force microscopy (AFM) data confirmed the results (Fig.
S17). These results suggested the formation of the
polypseudorotaxane.
School of Chemistry and Chemical Engineering, Shanxi University,
Taiyuan, 030006, P. R. China
c
6
5
Ministry of Education Key Laboratory of Interface Science and
Engineering in Advanced Materials, Taiyuan University of Technology,
Taiyuan, 030024, P.R. China; E-mail: wangpi@tyut.edu.cn
1
†
2
Electronic Supplementary Information (ESI) available: H NMR spectra,
D NOESY NMR spectra, 2D DOSY NMR spectra, FT-IR data, XRD
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DMP5 and trans-G1. Furthermore, the host–guest recognition
2
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a
photo-responsive
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