Kinetic Control of a Self-Assembly Pathway towards Hidden Chiral Microcoils

Article abstract of DOI:10.1002/chem.201901120

Manipulating the self-assembly pathway is essentially important in the supramolecular synthesis of organic nano- and microarchitectures. Herein, we design a series of photoisomerizable chiral molecules, and realize precise control over pathway complexity with external light stimuli. The hidden single-handed microcoils, rather than the straight microribbons through spontaneous assembly, are obtained through a kinetically controlled pathway. The competition between molecular interactions in metastable photostationary intermediates gives rise to a variety of molecular packing and thereby the possibility of chirality transfer from molecules to supramolecular assemblies.

Full text of DOI:10.1002/chem.201901120

A Journal of
Accepted Article
Title: Kinetic Control of Self-Assembly Pathway towards Hidden Chiral
Microcoils
Authors: Yongxian Guo, Yin Liu, Yanjun Gong, Wei Xiong, Chuang
Zhang, Jincai Zhao, and Yanke Che
This manuscript has been accepted after peer review and appears as an
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To be cited as: Chem. Eur. J. 10.1002/chem.201901120
Link to VoR: http://dx.doi.org/10.1002/chem.201901120
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Kinetic Control of Self-Assembly Pathway towards Hidden Chiral
Microcoils
#
#
Yongxian Guo, Yin Liu, Yanjun Gong, Wei Xiong, Chuang Zhang,* Jincai Zhao and Yanke Che*
Abstract: Manipulating the self-assembly pathway is essentially
important in the supramolecular synthesis of organic nano- and micro-
architectures. Here we design a series of photoisomerizable chiral
molecules, and realize the precise control over pathway complexity
with external light stimuli. The hidden single-handed microcoils, rather
than the straight microribbons via spontaneous assembly, are
obtained through the kinetics-controlled pathway. The competition
between molecular interactions in metastable photostationary
intermediates gives rise to the variety of molecular packing and
thereby the possibility of chirality transfer from molecules to
supramolecular assemblies.
metastable aggregates, then slowly disassemble and isomerize
back into trans-1 monomers. Importantly, this kinetics-controlled
pathway leads to the nucleation and elongation of single-handed
microcoils (Pathway B, Figure 1b), which is in sharp contrast to
the spontaneous self-assembly pathway towards the instant
formation of straight microribbons (Pathway A, Figure 1b).
Structural and optical characterizations show that the pathway
complexity originates from the molecular interaction competition
and gives rise to various supramolecular assemblies. Here, our
finding, i.e., using a kinetics-controlled pathway to introduce extra
molecular interaction for the formation of hidden chiral microcoils,
provides a new example of utilizing the pathway complexity for
novel functional supramolecular materials.
Analogous to the formation and growth processes of protein
[
1-2]
fibrils,
pathway complexity has been discovered to involve in
the self-assembly process of many synthetic systems.[3-33]
Furthermore, pathway complexity has been proven to be critical
to achieve kinetically stable micro-/nano-architectures[8-16]and to
yield a living supramolecular polymerization.[
13,22-33]
For example,
Meijer and coworkers have selectively obtained the metastable
assemblies based on the systematical studies on the kinetics-
controlled pathway complexity.[8-9,12,17] Takeuchi et al. have first
reported the use of pathway complexity in the design and
realization of living supramolecular polymerization.[25] Despite the
many advances on pathway complexity in the supramolecular
self-assembly, facile and precise control over the pathways
toward specific assembly structures remains a great challenge in
practice. This is mainly because different pathways often proceed
concurrently and tangle together, thereby hindering the selective
synthesis of desired architectures. In addition, some of the
kinetically stable assemblies are deeply trapped in the energy
landscape and the thermodynamically stable assembly may not
Figure 1. (a) Molecular structures of molecule
1 and the reversible
transformation between trans and cis conformations induced by UV/visible light
irradiation. (b) Schematic illustration of pathway complexity in the self-assembly
of molecule 1, including the formation of microribbons by a spontaneous self-
assembly pathway (Pathway A), the formation of single-handed microcoils of
chiral molecular 1 and the formation of bent microribbons of racemic (R, S)-1 by
photo-initiated self-assembly pathways (Pathway B). The images in dashed
frames are the lattice parameters and internal organization of microribbons and
microcoils, respectively.
[
8-11, 24]
be accessed.
In this work, we report the pathway complexity in the self-
assembly of photoisomerizable chiral molecule 1 (Figure 1a), and
fabricate the hidden single-handed microcoils through a kinetics-
controlled pathway triggered by photoirradiation. We reveal that
the photoirradiation at the initial self-assembly stage can
photoisomerize trans-1 into cis-1 molecules, which firstly form
As shown in Figure 1a, chiral molecules, (S)-1, (R)-1, and racemic
molecule (R, S)-1 that bear indigo and azobenzene moieties were
designed and synthesized (see Supporting Information, Scheme
S1, Figure S1 to S8 for details), and their pathway complexity of
self-assembly under photoirradiation was investigated. Given the
reversible photoisomerization of azobenzene moieties in 1 that
can create distinct intermolecular interactions, the photoregulated
self-assembly property of 1 is expected. Furthermore, by
modulating the photoisomerization extent and rate of 1 with light
irradiation, the precise control on the concentration of trans-/cis-
[
*]
Y. Guo, Y. Liu, Y. Gong, W. Xiong, Prof. Dr. C. Zhang, Prof. Dr. J.
Zhao, Prof. Dr. Y. Che
Key Laboratory of Photochemistry, CAS Research/Education Center
for Excellence in Molecular Sciences, Institute of Chemistry,
Chinese Academy of Sciences, Beijing 100190, China
and
University of Chinese Academy of Sciences, Beijing 100049, China
E-mail: zhangc@iccas.ac.cn; ykche@iccas.ac.cn
These authors contributed equally to this work.
[#
[34-35]
]
monomers can be achieved, analogues to other systems.
Before exploring the pathway complexity, we characterized the
photoisomerization behaviors of molecularly dissolved trans-1 by
measuring its absorption spectra (Figure S9) in solution upon UV
Supporting information for this article is given via a link at the end of
the document.
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irradiation (350-380 nm). During the 10 min irradiation, the π-π*
absorption of trans-1 around 360 nm gradually decreased, while
the absorption band centered at ca. 450 nm corresponding to the
n-π* transition of cis-1 increased. This result indicates that the
trans to cis photoisomerization occurred rapidly. The yielded ratio
of trans-1 to cis-1 after UV radiation was quantified to be 20:80
1 and trans-(R, S)-1 share the same molecular packing mode as
those of trans-(S)-1, regardless of the opposite point chirality in
the substituent. These results demonstrate that π-π interaction
outcompetes other molecular interactions such as the chirality
transfer, and dominates the fast nucleation-elongation of
molecule 1 into ribbon structures.
1
according to the H NMR spectra of the photostationary product
(
Figure S10). The reaction rate of cis-1 to trans-1 isomerization is
slow in the dark and the cis-1 molecules exist for several hours
Figure S11). Visible light (420-700 nm) can increase the rate of
(
reversion reaction by over 1000 times (Figure S12), thereby
offering an alternative way to the kinetic control over the trans-
/cis- monomer concentrations. Importantly, self-assembly of
trans-1 with kinetically controlled concentration serves as a new
self-assembly pathway, thereby providing opportunities to
construct assemblies with unusual microscale architectures.
Figure 3. SEM images of the assembly evolution of (S)-1 (a-i) and (R)-1 (j-r) at
different time points. (a) Schematic illustration of morphology evolution by
photo-initiated self-assembly process of (S)-1. (b) Nanospheres formed at 2 min
after adding the UV irradiated (S)-1 monomer into methanol. (c) Microscale
irregular aggregate formed at 30 min from the deformation of nanospheres. (d,
e) Curved chiral nucleus formed at 1 h. (f, g) Nanospheres aggregates onto the
termini of the tubular ribbons for epitaxial growth at 8h. (h, i) Single-handed
microcoils formed at 24 h. (j-r) are the same as (a-i) but for (R)-1.
Figure 2. SEM images of microribbons assembled from trans-(S)-1 (a-c), trans-
(
(
R)-1 (d-f), and trans-(R, S)-1 (g-i) at different time points: 2 min (a, d, g), 24 h
b, e, h), and amplified images (c, f, i).
We next explored the kinetics-controlled self-assembly of trans-1
We first used scanning electronic microscopy (SEM) to monitor
the spontaneous self-assembly process of pure trans-1 (Pathway
A). As shown in Figure 2a-c, the ribbon-like structures with lengths
of several micrometers were formed immediately after fully mixing
(Pathway B), where the trans-1 concentration in monomers
depends on the kinetic reversion from cis-1 to trans-1. In a typical
self-assembly process, a chloroform solution (0.1 mL) of trans-
4
(
S)-1 molecule (4.2 × 10- M) was firstly irradiated by 365 nm UV
0
.1 mL chloroform solution of trans-(S)-1 (4.2 × 10-4 M) with 1.5
2
light (10 mW/cm ) for 10 min to yield a mixture of trans-1 and cis-
mL methanol as the poor solvent (see details in the Supporting
Information). The morphology of resulting products remained
unchanged even after 30 days (Figure S13), showing that these
assemblies are thermodynamically stable structures. The crystal
structure of these ribbons was analyzed by X-ray diffraction (XRD)
and selected area electron diffraction (SAED) measurement,
thereby the molecular packing of the ribbons can be simulated
accordingly (Figure S14). A closer examination showed that the
distance between neighboring indigo moieties is 3.55 Å,
suggesting that the π-π interaction was the dominant driving force
for the ribbon formation. Notably, trans-(R)-1 and trans-(R, S)-1
molecules also self-assembled into ribbon-like structures under
the same self-assembly conditions (Figure 2d-i). XRD
measurements (Figure S15) proved that the ribbons of trans-(R)-
1
(20:80), and then injected into 1.5 mL methanol followed by
stirring and aging in the dark. Interestingly, spherical
nanoparticles with diameters ranging from 100 nm to 150 nm were
formed at 2 min after the beginning the self-assembly process
(
Figure 3b and Figure S16). Then these nanospheres evolved into
curved structures and bounded together (Figure 3c). At 1 h, well-
defined cambered structures were observed (Figure 3d, e),
indicative of the formation of new trans-(S)-1 structural nuclei. As
time progressed, the cambered nuclei continued to grow into
microscale coiled structures (Figure 3f, g). A closer examination
revealed that the microcoil ends were irregular at this stage, which
were still accompanied with small curved structures and a small
number of nanospheres (Figure 3g). After 24 h, only large trans-
(S)-1 microcoils with a diameter of ca. 2 µm and a length of ca. 10
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2
µm were observed without the existence of small curved
structures and nanospheres (Figure 3h, i and Figure S17).
The above observations suggest that the nanospheres
intermediates slowly disassembled into monomers that could
form cambered nuclei and grow into well-defined microcoils,
analogous to the metastable aggregates involved in other
supramolecular systems that mediate the nucleation and growth
365 nm UV light (10 mW/cm ) for 10 min to yield trans-1:cis-
1=20:80 monomers and then injected into 1.5 mL methanol
followed by fully stirring and aging in the dark. At 2 min after
beginning the self-assembly process, nanospheres was initially
formed (Figure 4b), and then evolved into curved structures
(Figure 4c). Unlike the case of (S)-1 or (R)-1, these curved
assemblies of (R, S)-1 exhibited no preferential helicity (Figure 4d,
e) and grew into randomly bent microribbons along with a
decreasing number of nanospheres as time progressed (Figure
4f, g). After 24 h, only well-defined bent microribbons were
observed, indicating that all metastable aggregates were
disassembled for the microribbon growth. XRD and SAED
patterns showed that the resulting bent microribbons (Figure S24)
are different in crystal structures from those (S)-1 or (R)-1
microcoils, but consistent with the microribbons obtained by
spontaneous self-assembly pathway (Figure S14). These
observations illustrate that the chirality transfer of chiral 1 is
necessary for the formation of single-handed coiled structures at
the nucleation stage of kinetics-controlled self-assembly. The
molecular interaction that drove the formation of nanospheres
was also revealed by optical characterization. The absorption of
nanospheres suspension obtained at 2 min (Figure S25) is similar
to that of UV-irradiated monomer solution, showing that the
building blocks of nanosphere are mainly cis- 1 molecules. This
result indicates that the formation of metastable nanospheres was
mainly driven by the steric repulsion among photogenerated cis-
1 molecules. We also performed XRD measurements of the
metastable nanosphere assemblies. No XRD peaks were
observed from the nanosphere aggregates due to their
amorphous structural nature. After 1 h, XRD features of ordered
molecular packing appeared (Figure S26), suggesting that the
cooperative effect among π-π interaction, steric interaction, and
chirality transfer (existing only for chiral 1) began to mediate the
nucleation of assemblies.
[
25,27]
of stable structures.
The building blocks of the obtained
microcoils are trans-1 molecules revealed by measuring the
absorption spectrum of microcoils suspension (Figure S18).
Notably, the resulting microcoils are all single-handed (P-type) as
revealed in magnified SEM images (Figure S19) and transmission
electron microscopy (TEM) images (Figure S20). In accordance
with the results of XRD and SAED, we simulated the molecular
packing of trans-(S)-1 and calculated the distance between indigo
moieties in microcoils to be 3.84 Å (Figure S21). The larger
intermolecular spacing compared with that in microribbons
suggests the cooperative interactions among π-interaction, steric
interaction, and chirality transfer dominantly drive the formation of
[
36-38]
microcoils.
Likewise, the stepwise formation of microcoils from trans-(R)-1
monomers was observed through the kinetics-controlled self-
assembly Pathway
B (Figure 3j-r). Instead, the resulting
microcoils were M-type assemblies (Figure S22). XRD
measurements confirmed a similar molecular packing (Figure
S23) but in mirror image. These results indicate that the transfer
of point chirality becomes critical in the interaction competition
and gives rise to single-handed microcoils in the kinetics-
controlled self-assembly pathway. This is in sharp contrast with
the spontaneous self-assembly of pure trans-1 monomer (Path-
way A) where the transfer of point chirality was outcompeted by
π-π interaction.
The kinetic reversion rate from cis to trans form can also influence
on the interaction competition and consequently on the
morphology of the resulting assemblies. We applied visible light
2
irradiation (420-700 nm, 100 mW/cm ) on metastable cis-1
nanospheres to facilitate the formation of trans-1. As shown in
Figure S27, straight microribbons with ca. 3 µm in width and ca.
40 µm in length were immediately formed after 5 min under visible
irradiation. XRD measurements showed that these rapidly formed
ribbons have the same molecular packing (Figure S28) as the
ribbons from the spontaneous assembly of trans-1 (Pathway A).
Obviously, the concentration of trans-1 monomer significantly
increases under this condition, which allows π-π interaction to be
the dominant driving force that leads to the formation of
microribbons. This result further indicates that the formation of
microcoils necessitates the kinetics-controlled self-assembly
pathway with a proper interaction competition.
In conclusion, we present the self-assembly pathway complexity
of molecule 1 that involves distinct competition of molecular
interactions and thereby results in assemblies with diverse
morphologies. Particularly, the fabrication of hidden single-
handed microcoils is achieved through the kinetics-controlled self-
assembly pathway, where the photoirradiation on chiral trans-1 at
the initial self-assembly stage introduces the morphological
transition from metastable nanospheres to cambered nuclei and
to single-handed microcoils. Our results prove the importance of
Figure 4. SEM images of the assembly evolution of (R, S)-1 at different time
points. (a) Schematic illustration of morphology evolution by the photo-initiated
self-assembly of (R, S)-1 molecules. (b) Nanospheres formed at 2 min after
adding UV-irradiated (R, S)-1 monomer into methanol. (c) Microscale curved
aggregates formed at 30 min from the deformation of nanospheres. (d, e)
Achiral nucleus formed at 1 h. (f, g) Nanospheres aggregate onto the termini of
bent ribbons for epitaxial growth at 8 h. (h, i) Achiral bent microribbons formed
at 24 h.
To further understand how the interaction competition leads to the
morphological transition in Pathway B, we monitored the kinetics-
controlled self-assembly of (R, S)-1 (Figure 4a) that lacks the
point chirality. Similar to (S)-1 or (R)-1, chloroform solution (0.1
mL) of (R, S)-1 molecule (4.2 × 10-4 M) was firstly irradiated by
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pathway complexity in achieving novel microscale architectures
in the synthetic systems, and offer a photochemical method to
manipulate self-assembly pathways towards precisely controlled
synthesis of supramolecular assemblies.[39-42]
[17] M. F. J. Mabesoone, A. J. Markvoort, M. Banno, T. Yamaguchi, F.
Helmich, Y. Naito, E. Yashima, A. R. A. Palmans, E. W. Meijer, J. Am.
Chem. Soc. 2018, 140, 7810-7819.
[
18] S. Ogi, V. Stepanenko, J. Thein, F. Würthner, J. Am. Chem. Soc. 2016,
38, 670-678.
19] X. Ma, Y. Zhang, Y. Zhang, C. Peng, Y. Che, J. Zhao, Adv. Mater. 2015,
7, 7746-7751.
[20] S. Matsubara, H. Tamiaki, J. Am. Chem. Soc. 2019, 141, 1207-1211.
1
[
2
Acknowledgements
[
[
[
[
21] P. Xing, P. Li, H. Chen, A. Hao, Y. Zhao, Acs Nano 2017, 11, 4206-4216.
22] J. S. Valera, R. GoMez, L. Sanchez, Small 2018, 14, 1702437.
23] S. Ogi, C. Grzeszkiewicz, F. Würthner, Chem. Sci. 2018, 9, 2768-2773.
24] T. Fukui, S. Kawai, S. Fujinuma, Y. Matsushita, T. Yasuda, T. Sakurai,
S. Seki, M. Takeuchi, K. Sugiyasu, Nat. Chem. 2017, 9, 493-499.
This work was supported by the “National Key R&D Program of
China” (No. 2018YFA0209302), the National Natural Science
Foundation of China (Nos. 21577147, 21590811 and 21677148),
and the “Key Research Program of Frontier Sciences” (No.
QYZDY-SSW-SLH028) of the Chinese Academy of Sciences.
[25] S. Ogi, K. Sugiyasu, S. Manna, S. Samitsu, M. Takeuchi, Nat. Chem.
2014, 6, 188-195.
[
[
[
26] M. Endo, T. Fukui, S. H. Jung, S. Yagai, M. Takeuchi, K. Sugiyasu, J.
Am. Chem. Soc. 2016, 138, 14347-14353.
Keywords: Azobenzene • photoisomerization • Kinetic control •
27] X. Ma, Y. Zhang, Y. Zhang, Y. Liu, Y. Che, J. Zhao, Angew. Chem. Int.
Ed. 2016, 55, 9539-9543; Angew. Chem. 2016, 128, 9691-9695.
28] Y. Liu, C. Peng, W. Xiong, Y. Zhang, Y. Gong, Y. Che, J. Zhao, Angew.
Chem. Int. Ed. 2017, 56, 11380-11384; Angew. Chem. 2017, 129,
11538-11542.
Pathway Complexity • Chirality
[1]
[2]
[3]
A. M. Mulder, Science 2010, 330, 673-677.
E. T. Powers, D. L. Powers, Biophys. J. 2008, 94, 379-391.
J. M. A. Carnall, C. A. Waudby, A. M. Belenguer, M. C. A. Stuart, J. J.-P.
Peyralans, S. Otto, Science 2010, 327, 1502-1506.
[29] M. E. Robinson, A. Nazemi, D. J. Lunn, D. W. Hayward, C. E. Boott, M.
S. Hsiao, R. L. Harniman, S. A. Davis, G. R. Whittell, R. M. Richardson,
L. D. Cola, I. Manners, Acs Nano 2017, 11, 9162-9175.
[4]
D. V. D. Zwaag, P. A. Pieters, P. A. Korevaar, A. J. Markvoort, A. J. H.
Spiering, T. F. A. D. Greef, , E. W. Meijer, J. Am. Chem. Soc. 2015, 137,
[30] M. E. Robinson, D. J. Lunn, A. Nazemi, G. R. Whittell, L. D. Cola, I.
Manners, Chem. Comm. 2015, 51, 15921-15924.
12677-12688.
[5]
[6]
[7]
[8]
S. Ogi, T. Fukui, J. Melinda L, M. Takeuchi, K. Sugiyasu, Angew. Chem.
Int. Ed. 2014, 53, 14363-14367; Angew. Chem. 2014, 126, 14591-14595.
E. E. Greciano, B. Matarranz, n. L. Sanchez, Angew. Chem. Int. Ed. 2018,
[31] S. Ogi, K. Matsumoto, S. Yamaguchi, Angew. Chem. Int. Ed. 2018, 57,
2339-2343; Angew. Chem. 2018, 130, 2363-2367.
[32] S. Ogi, V. Stepanenko, K. Sugiyasu, M. Takeuchi, F. Würthner, J. Am.
Chem. Soc. 2015, 137, 3300-3307.
5
7, 4697-4701; Angew.Chem. 2018, 130, 4787-4791.
J. W. Sadownik, E. Mattia, P. Nowak, S. Otto, Nat. Chem. 2016, 8, 264-
69.
[33] J. Boekhoven, J. M. Poolman, C. Maity, F. Li, L. van der Mee, C. B.
Minkenberg, E. Mendes, J. H. van Esch, R. Eelkema, Nat. Chem. 2013,
5, 433-437.
2
P. A. Korevaar, S. J. George, A. J. Markvoort, M. M. J. Smulders, P. A.
J. Hilbers, A. P. H. J. Schenning, T. F. A. D. Greef, E. W. Meijer, Nature
[34] C. E. Weston, R. D. Richardson, P. R. Haycock, A. J. P. White, M. J.
Fuchter, J. Am. Chem. Soc. 2014, 136, 11878-11881.
2012, 481, 492-496.
[
[
9]
A. T. Haedler, S. C. J. Meskers, R. H. Zha, M. Kivala, H. W. Schmidt, E.
[35] J. Calbo, C. E. Weston, A. J. P. White, H. S. Rzepa, J. Contreras-García,
M. J. Fuchter, J. Am. Chem. Soc. 2017, 139, 1261-1274.
[36] I. Danila, F. Riobe, F. Piron, J. Puigmarti-Luis, J. D. Wallis, M. Linares,
H. Agren, D. Beljonne, D. B. Amabilino, N. Avarvari, J. Am. Chem. Soc.
2011, 133, 8344-8353.
W. Meijer, J. Am. Chem. Soc. 2016, 138, 10539-10545.
10] F. Tantakitti, J. Boekhoven, X. Wang, R. V. Kazantsev, T. Yu, J. Li, E.
Zhuang, R. Zandi, J. H. Ortony, C. J. Newcomb, L. C. Palmer, G. S.
Shekhawat, M. O. de la Cruz, G. C. Schatz, S. I. Stupp, Nat. Mater. 2016,
1
5, 469-476.
[37] W. Zhang, W. Jin, T. Fukushima, N. Ishii, T. Aida, J. Am. Chem. Soc.
2013, 135, 114-117.
[
11] Y. Zhang, Y. Zheng, W. Xiong, C. Peng, Y. Zhang, R. Duan, Y. Che, J.
Zhao, Sci. Rep. 2016, 6, 27335.
[38] W. Zhang, W. Jin, T. Fukushima, T. Mori, T. Aida, J. Am. Chem. Soc.
2015, 137, 13792-13795.
[
12] P. A. Korevaar, C. J. Newcomb, E. W. Meijer, S. I. Stupp, J. Am. Chem.
Soc. 2014, 136, 8540-8543.
[39] I. Danila, F. Pop, C. Escudero, L. N. Feldborg, J. Puigmarti-Luis, F. Riobe,
N. Avarvari, D. B. Amabilino, Chem. Commun. 2012, 48, 4552-4554.
[40] F. Pop, C. Melan, I. Danila, M. Linares, D. Beljonne, D. B. Amabilino, N.
Avarvari, Chem. Eur. J. 2014, 20, 17443-17453.
[
13] A. Aliprandi, M. Mauro, L. D. Cola, Nat. Chem. 2016, 8, 10-15.
14] B. Kemper, L. Zengerling, D. Spitzer, R. Otter, T. Bauer, P. Besenius, J.
Am. Chem. Soc. 2018, 140, 534-537.
[
[
15] J. S. Valera, R. Gómez, L. Sanchez, Angew. Chem. Int. Ed. 2019, 58,
[41] L. Zhang, T. Wang, Z. Shen, M. Liu, Adv. Mater. 2016, 28, 1044-1059.
[42] J. Jiang, Y. Meng, L. Zhang, M. Liu, J. Am. Chem. Soc. 2016, 138,
15629-15635.
510-514; Angew.Chem. 2019, 131,520-524.
[16] Y. Wang, R. M. de Kruijff, M. Lovrak, X. Guo, R. Eelkema, J. H. van Esch,
Angew. Chem. Int. Ed. 2019, 58, 3800-3803; Angew. Chem. 2019, 131,
3840-3843.
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Entry for the Table of Contents
COMMUNICATION
#
#
Pathway complexity achieved by
chiral molecule 1, which obtained
chiral expressed single-handed
microcoils by photo-initiated kinetic
controlled self-assembly pathway B,
ribbon-like architectures obtained by
spontaneous self-assembly pathway A
without chiral expression. Distinct
competition of molecular interactions
among π-π interaction, steric
Yongxian Guo, Yin Liu, Yanjun Gong,
Wei Xiong, Chuang Zhang,* Jincai Zhao
and Yanke Che*
Page No. – Page No.
Kinetic Control of Self-Assembly
Pathway towards Hidden Chiral
Microcoils
interaction, and chirality transfer is the
mainspring of the pathway
differentiation.
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