Myongsoo Lee

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Organization: Jilin University
Department: College of Chemistry
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Co-reporter:Xi Chen;Yanqiu Wang;Huaxin Wang;Yongju Kim
Chemical Communications 2017 vol. 53(Issue 79) pp:10958-10961
Publication Date(Web):2017/10/03
DOI:10.1039/C7CC05869A
We report peptide vesicles with chiral membranes as enantioselective nanoreactors. The peptide vesicles are able to selectively encapsulate only a single enantiomer from a racemic mixture solution through preferential diffusion across the membranes. Notably, the confined space of the vesicle acts as an enantioselective nanoreactor for the encapsulated enantiomer which undergoes further chemical transformations to yield a highly enantiopure product.
Co-reporter:Xi Chen; Ying He; Yongju Kim
Journal of the American Chemical Society 2016 Volume 138(Issue 18) pp:5773-5776
Publication Date(Web):April 14, 2016
DOI:10.1021/jacs.6b02401
Although significant progress has been achieved with short peptide nanostructures, the construction of switchable membrane assemblies remains a great challenge. Here we report short α-peptide assemblies that undergo thermo-reversible switching between assembly and disassembly states, triggered by the conformational change of laterally grafted short peptides from a folded α-helix to a random coil conformation. The α-helical peptide based on two oligoether dendron side groups forms flat disks, while the peptide helix based on three dendron side groups forms hollow vesicles. The vesicular membrane can spontaneously capture a racemic mixture through the self-formation of vesicular containers upon heating and enantioselectively release the chiral guest molecule through preferential diffusion across the vesicular walls.
Co-reporter:Guangren Na, Ying He, Yongju Kim and Myongsoo Lee  
Soft Matter 2016 vol. 12(Issue 11) pp:2846-2850
Publication Date(Web):18 Feb 2016
DOI:10.1039/C5SM03073K
We report switchable, fluorescent carbohydrate nanofibers formed through the self-assembly of aromatic rod amphiphiles with a combination of mannose epitopes and thermoresponsive oligoether dendrons. The carbohydrate nanofibers undergo reversible switching between carbohydrate-exposed and hidden states on their surface in response to a thermal signal, and have the ability to regulate cell proliferation.
Co-reporter:Bowen Shen;Ying He;Dr. Yongju Kim;Yanqiu Wang ; Myongsoo Lee
Angewandte Chemie International Edition 2016 Volume 55( Issue 7) pp:2382-2386
Publication Date(Web):
DOI:10.1002/anie.201509190

Abstract

One of the great challenges in molecular self-assembly is how to confer self-folding and closing characteristics on flat two-dimensional structures in response to external triggers. Herein, we report a planar ribbon assembly that folds into closed tubules in response to fructose. The ribbons, ≈28 nm wide and 3.5 nm thick, consist of 8 laterally-associated elementary fibrils in which disc-shaped macrocycle amphiphiles are stacked along their axis. Upon addition of fructose, these flat structures spontaneously fold into closed tubules, with an outer diameter of ≈8 nm, through zipping of the two sides of the ribbons. Notably, the folding and then zipping of the flat ribbons is accompanied by spontaneous capture of the fructose molecules inside the tubular cavities.

Co-reporter:Bowen Shen;Ying He;Dr. Yongju Kim;Yanqiu Wang ; Myongsoo Lee
Angewandte Chemie 2016 Volume 128( Issue 7) pp:2428-2432
Publication Date(Web):
DOI:10.1002/ange.201509190

Abstract

One of the great challenges in molecular self-assembly is how to confer self-folding and closing characteristics on flat two-dimensional structures in response to external triggers. Herein, we report a planar ribbon assembly that folds into closed tubules in response to fructose. The ribbons, ≈28 nm wide and 3.5 nm thick, consist of 8 laterally-associated elementary fibrils in which disc-shaped macrocycle amphiphiles are stacked along their axis. Upon addition of fructose, these flat structures spontaneously fold into closed tubules, with an outer diameter of ≈8 nm, through zipping of the two sides of the ribbons. Notably, the folding and then zipping of the flat ribbons is accompanied by spontaneous capture of the fructose molecules inside the tubular cavities.

Co-reporter:Yuntian Yang, Junjie Cui, Zhaohua Li, Keli Zhong, Long Yi Jin, and Myongsoo Lee
Macromolecules 2016 Volume 49(Issue 16) pp:5912-5920
Publication Date(Web):August 2, 2016
DOI:10.1021/acs.macromol.6b01347
Amphiphilic coil–rod–coil molecules 1–3, consisting of an n-shaped rod building block and poly(ethylene oxide) (PEO) with a degree of polymerization of 5 linked through a biphenyl unit as the coil segment, were synthesized. Molecule 1 self-assembles into lamellar and hexagonal perforated layer structures, in the crystalline and liquid crystalline phases, respectively. Remarkably, molecule 2 incorporating lateral methyl groups between the rod and coil segments spontaneously self-organizes into hexagonal perforated layer and oblique columnar structures. The additional incorporation of a lateral butyl group at the center of the rod segment of molecule 2 generates molecule 3, which assumes an exclusively oblique columnar structure in the solid state. In aqueous solutions, molecule 1 self-assembles into fibrous aggregates, whereas molecules 2 and 3 exhibit a self-organizing capacity to form helical fibers. Additionally, circular dichroism (CD) experiments and atomic force microscope (AFM) measurements of molecule 3 highlight a switch of the helical sense to the opposite handedness, depending on the temperature of the aqueous solution.
Co-reporter:Zhuoshi Wang;Keli Zhong;Yongri Liang;Tie Chen;Bingzhu Yin;Long Yi Jin
Journal of Polymer Science Part A: Polymer Chemistry 2015 Volume 53( Issue 1) pp:85-92
Publication Date(Web):
DOI:10.1002/pola.27448

ABSTRACT

A new class of π-conjugated, skewed H-shaped oligomers, consisting of biphenyl, phenylene vinylene, and phenylene ethynylene units as the rigid segment, were synthesized via Sonogashira coupling and Wittig reactions. The coil segments of these molecules were composed of poly(ethylene oxide) (PEO) or PEO with lateral methyl groups between the rod and coil segment, respectively. The experimental results revealed that the lateral methyl groups attached to the surface of the rod and coil segments dramatically influenced the self-assembling behavior of the molecules in the crystalline phase. H-shaped rod–coil molecules containing a lateral methyl group at the surface of the rod and PEO coil segments self-assemble into a two-dimensional columnar or a three-dimensional body-centered tetragonal nanostructures in the crystalline phase, whereas molecules lacking a lateral methyl group based on the PEO coil chain self-organize into lamellar or hexagonal perforated lamellar nanostructures. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 85–92

Co-reporter:Dr. Ho-Joong Kim;Dr. Yongju Kim;Dr. Sung Cho;Dr. Myongsoo Lee
Chemistry - A European Journal 2015 Volume 21( Issue 33) pp:11836-11842
Publication Date(Web):
DOI:10.1002/chem.201500780

Abstract

Threefold symmetric rigid-core molecules with an internally grafted poly(ethylene oxide) (PEO) chain were synthesized, and their self-assembled structures were characterized using differential scanning calorimetry, TEM, and 1D and 2D X-ray scatterings in the solid state. The tripod compounds based on short PEO chains (n=8, 13, 17, 21), self-assemble into 2D channel-like network structures, whereas the compound with the longest PEO chain (n=34) forms a lamellar liquid crystalline phase. The interiors of the channel structures are filled with flexible PEO chains along the double-walled aromatic circumference. In these channel-like networks, three aromatic rods connected in the meta-position to each other are superimposed in parallel to other adjacent molecules to form the double-walled aromatic frameworks stacked perpendicular to the resulting channels. These are novel examples of supramolecular channel-like structures developed using amphiphilic diblock molecules based on a threefold symmetric rigid scaffold.

Co-reporter:Dr. Yongju Kim ;Dr. Myongsoo Lee
Chemistry - A European Journal 2015 Volume 21( Issue 15) pp:5736-5740
Publication Date(Web):
DOI:10.1002/chem.201500101

Abstract

Self-assembly of polyaromatic systems has proved to be a powerful technique to construct nanoscale optoelectronic materials. However, attempts to develop self-assembled nanomaterials guided by pristine polyaromatic molecules have been limited. Here the construction of photoactive nanocapsules through the scission of an aromatic bilayer membrane driven by curved corannulene intercalation is reported. The framework of the capsule consists of the lateral array of corannulene, a buckyball fragment. The supramolecular capsules exhibit photocatalytic activity to degrade encapsulated fluorescein dye molecules under sunlight irradiation.

Co-reporter:Yanqiu Wang ; Zhegang Huang ; Yongju Kim ; Ying He
Journal of the American Chemical Society 2014 Volume 136(Issue 46) pp:16152-16155
Publication Date(Web):November 5, 2014
DOI:10.1021/ja510182x
The highlight of self-assembly is the reversibility of various types of noncovalent interactions which leads to construct smart nanostructures with switchable pores. Here, we report the spontaneous formation of inflatable nanofibers through the formation of hollow internal channels triggered by guest encapsulation. The molecules that form this unique nanofibers consist of a bent-shaped aromatic segment connected by a m-pyridine unit and a hydrophilic dendron at its apex. The aromatic segments self-assemble into paired dimers which stack on top of one another to form thin nanofibers with pyridine-functionalized aromatic cores. Notably, the nanofibers reversibly inflate into helical tubules through the formation of hollow cavities triggered by p-phenylphenol, a hydrogen-bonding guest. The reversible inflation of the nanofibers arises from the packing rearrangements in the aromatic cores from transoid dimers to cisoid macrocycles driven by the reversible hydrogen-bonding interactions between the pyridine units of the aromatic cores and the p-phenylphenol guest molecules.
Co-reporter:Woochul Lee, Dong-Woo Lee, Myongsoo Lee and Jong-In Hong  
Chemical Communications 2014 vol. 50(Issue 94) pp:14851-14854
Publication Date(Web):06 Oct 2014
DOI:10.1039/C4CC05929H
Aromatic amphiphiles were self-assembled into 2-D nanosheets and 1-D nanofibers by systematically varying the volume fraction of the hydrophilic coils, which enabled the direct exfoliation of carbon allotropes with high quality and quantity. A 2-D nanosheet structure was introduced as the hole transporting layer for improving the performance of organic photovoltaic devices.
Co-reporter:Wen Li, Yongju Kim, Jingfang Li and Myongsoo Lee  
Soft Matter 2014 vol. 10(Issue 29) pp:5231-5242
Publication Date(Web):04 Jun 2014
DOI:10.1039/C4SM01068J
The construction of supramolecular polymers has been intensively pursued because the nanostructures formed through weak non-covalent interactions can be triggered by external stimuli leading to smart materials and sensors. Self-assemblies of coordination polymers consisting of metal ions and organic ligands in aqueous solution also provide particular contributions in this area. The main motivation for developing those coordination polymers originates from the value-added combination between metal ions and ligands. This review highlights the recent progress of the dynamic self-assembly of coordination polymers that result from the sophisticated molecular design, towards fabricating stimuli-responsive systems and bio-related materials. Dynamic structural changes and switchable physical properties triggered by various stimuli are summarized. Finally, the outlook for aqueous nanostructures originated from the dynamic self-assembly of coordination polymers is also presented.
Co-reporter:Shen Chen ; Cong Ma ; Zhegang Huang
The Journal of Physical Chemistry C 2014 Volume 118(Issue 15) pp:8181-8186
Publication Date(Web):March 24, 2014
DOI:10.1021/jp500366w
Despite recent advances in synthetic nanometer-scale helical assembly, control of supramolecular chirality remains a challenge. Here, we describe the fine-tuning of the shape and morphology transitions of twisted and helical assembly from dumbbell-shaped rigid-flexible amphiphile triggered by concentration. The amphiphile 2 self-assembles into nonchiral 3D columnar crystals with alternative packing of aromatic segment in solid state. Remarkably, with the addition of water into the solid, the achiral crystal transforms into 2D hexagonally ordered liquid crystal gel with supramolecular chirality due to increased entropy of flexible coil in aqueous environment. Notably, the helical liquid crystal gel was observed to dissolve into optically active aqueous nanofibers caused by a conformational change of hydrophobic aromatic rods and enhanced hydro-volume of the ethylene oxide chains.
Co-reporter:Yongju Kim, Wen Li, Suyong Shin, and Myongsoo Lee
Accounts of Chemical Research 2013 Volume 46(Issue 12) pp:2888
Publication Date(Web):September 23, 2013
DOI:10.1021/ar400027c
Toroidal nanostructures are symmetrical ring-shaped structures with a central internal pore. Interestingly, in nature, many transmembrane proteins such as β-barrels and α-helical bundles have toroidal shapes. Because of this similarity, toroidal nanostructures can provide a template for the development of transmembrane channels. However, because of the lack of guiding principles for the construction of toroids, researchers have not widely studied the self-assembly of toroidal nanostructures as compared with the work on other supramolecular architectures.In this Account, we describe our recent efforts to construct toroidal nanostructures through the self-assembly of rationally designed building blocks. In one strategy for building these structures, we induce interfacial curvatures within the building blocks. When we laterally graft a bulky hydrophilic segment onto a p-oligophenyl rod or β-sheet peptides, the backbones of the self-assembled structures can bend in response to the steric effect of these large side groups, driving the p-oligophenyl rod or β-sheet peptides to form nanosized toriods. In another strategy, we can build toroids from bent-shaped building blocks by stacking the macrocycles. Aromatic segments with an internal angle of 120° can associate with each other in aqueous solution to form a hexameric macrocycle. Then these macrocycles can stack on top of each other via hydrophobic and π–π interactions and form highly uniform toroidal nanostructures. We provide many examples that illustrate these guiding principles for constructing toroidal nanostructures in aqueous solution.Efforts to create toroidal nanostructures through the self-assembly of elaborately designed molecular modules provide a fundamental approach toward the development of artificial transmembrane channels. Among the various toroids that we developed, a few nanostructures can insert into lipid membranes and allow limited transport in vesicles.
Co-reporter:Wen Li, Yongju Kim and Myongsoo Lee  
Nanoscale 2013 vol. 5(Issue 17) pp:7711-7723
Publication Date(Web):14 Jun 2013
DOI:10.1039/C3NR02574H
The construction of supramolecular nanoscopic architectures has been intensively pursued because of their unique features for applications in nanoscience and biomimetic chemistry. Molecular self-assemblies of aromatic rod–coil amphiphiles consisting of rigid rod segments and hydrophilic flexible chains in aqueous solution provide a facile avenue into this area. This feature article highlights the recent progress regarding the construction of aqueous assemblies that result from the sophisticated design of aromatic rod–coils, with the aim to develop stimuli-responsive systems and bioactive materials. Important factors affecting the self-assembly morphologies are discussed and summarized. Dynamic structural changes triggered by temperature and guest molecules are demonstrated. Finally, the perspective of bioactive nanostructures originated from self-assembly of aromatic block amphiphiles is also introduced.
Co-reporter:Wen Li, Jingfang Li and Myongsoo Lee  
Chemical Communications 2013 vol. 49(Issue 74) pp:8238-8240
Publication Date(Web):17 Jul 2013
DOI:10.1039/C3CC44238A
Facial peptide P1 carrying repeating hydrophobic and hydrophilic residues as well as lysine terminals self-assemble into uniform toroid structures. The sensitive balance between the hydrophobic interactions and electrostatic repulsion dominates the formation of highly curved assemblies.
Co-reporter:Taehoon Kim, Hyojin Lee, Yongju Kim, Jwa-Min Nam and Myongsoo Lee  
Chemical Communications 2013 vol. 49(Issue 38) pp:3949-3951
Publication Date(Web):22 Mar 2013
DOI:10.1039/C3CC41215F
We have demonstrated that stable Concanavalin A (Con A)-coated supramolecular nanofibers can be constructed by complexation of self-assembled mannose nanofibers with Con A. The extended multivalent Con A nanofibers bind strongly to T cell surfaces and promote T cell activation.
Co-reporter:Zhuoshi Wang;Junjie Cui;Yongri Liang;Tie Chen;Bingzhu Yin;Long Yi Jin
Journal of Polymer Science Part A: Polymer Chemistry 2013 Volume 51( Issue 23) pp:5021-5028
Publication Date(Web):
DOI:10.1002/pola.26929

ABSTRACT

T-shaped coil–rod–coil oligomers, consisting of a dibenzo[a,c]phenazine unit and phenyl groups linked together with acetylenyl bonds at the 2,7-position of dibenzo[a,c]phenazine as a rigid segment have been synthesized. The coil segments of these new molecules composed of poly(ethylene oxide) (PEO)–poly(propylene oxide) (PPO) incorporating lateral methyl groups between the rod and coil segment and two flexible alkyl groups connecting with the rigid segment at the 4,6-position of dibenzo[a,c]phenazine, respectively. The experimental results reveal that the length of the flexible PEO coil chain influence construction of various supra-nanostructures from lamellar structure to rectangular columnar structure. It is also shown that introduction of different length of alkyl side chain groups in the backbone of the T-shaped molecules affect the self-organization behavior to form hexagonal perforate layer or oblique columnar structures. In addition, lateral methyl groups attached to the surface of rod and coil segments, dramatically influence the self-assembling behavior in the crystalline phase. T-shaped molecules containing a lateral methyl group at the surface of rod and PEO coil segments, self-assemble into 3D body-centered tetragonal structures in the crystalline phase, while molecules without a lateral methyl group based on PEO coil chain self-organize into 2D oblique columnar crystalline structures. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 5021–5028

Co-reporter:Yongju Kim;Suyong Shin;Taehoon Kim;Dongseon Lee; Chaok Seok; Myongsoo Lee
Angewandte Chemie 2013 Volume 125( Issue 25) pp:6554-6557
Publication Date(Web):
DOI:10.1002/ange.201210373
Co-reporter:Yongju Kim;Suyong Shin;Taehoon Kim;Dongseon Lee; Chaok Seok; Myongsoo Lee
Angewandte Chemie International Edition 2013 Volume 52( Issue 25) pp:6426-6429
Publication Date(Web):
DOI:10.1002/anie.201210373
Co-reporter:Wen Li, Jingfang Li and Myongsoo Lee
Chemical Communications 2013 - vol. 49(Issue 74) pp:NaN8240-8240
Publication Date(Web):2013/07/17
DOI:10.1039/C3CC44238A
Facial peptide P1 carrying repeating hydrophobic and hydrophilic residues as well as lysine terminals self-assemble into uniform toroid structures. The sensitive balance between the hydrophobic interactions and electrostatic repulsion dominates the formation of highly curved assemblies.
Co-reporter:Taehoon Kim, Hyojin Lee, Yongju Kim, Jwa-Min Nam and Myongsoo Lee
Chemical Communications 2013 - vol. 49(Issue 38) pp:NaN3951-3951
Publication Date(Web):2013/03/22
DOI:10.1039/C3CC41215F
We have demonstrated that stable Concanavalin A (Con A)-coated supramolecular nanofibers can be constructed by complexation of self-assembled mannose nanofibers with Con A. The extended multivalent Con A nanofibers bind strongly to T cell surfaces and promote T cell activation.
Co-reporter:Woochul Lee, Dong-Woo Lee, Myongsoo Lee and Jong-In Hong
Chemical Communications 2014 - vol. 50(Issue 94) pp:NaN14854-14854
Publication Date(Web):2014/10/06
DOI:10.1039/C4CC05929H
Aromatic amphiphiles were self-assembled into 2-D nanosheets and 1-D nanofibers by systematically varying the volume fraction of the hydrophilic coils, which enabled the direct exfoliation of carbon allotropes with high quality and quantity. A 2-D nanosheet structure was introduced as the hole transporting layer for improving the performance of organic photovoltaic devices.
N-diazoimidazole-1-sulfonamide
Boronic acid, [4'-(trimethylsilyl)[1,1'-biphenyl]-4-yl]-
L-PHENYLALANINE, N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-4-(PHENYLAZO)-
L-Norleucine, 6-azido-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-
Mannose
2,​5-​Diiodophenol
Z-D-PHE-NH2
dibenzo[ghi,mno]fluoranthene
3',6'-Dihydroxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one