Supramolecular Polymerization with Dynamic Self-Sorting Sequence Control

Synthetic polymerization and supramolecular polymerization with sequence control is far from an easy task. Herein, a narcissistic self-sorting supramolecular polymer is prepared with a sequence of (−AA−BB−)n by using cucur-bit[8]uril (CB[8])-based ternary complexes as supramolecular monomers, which are spontaneously formed from starting materials of heteroditopic AB-type guest and CB[8]. The process of supramolecular polymerization and their structural changes at each stage of polymerization have been successfully demonstrated by NMR, UV-Vis and fluorescence spectra. The self-sorting starts from the second step of polymerization after the formation of different ternary complexes as supra-monomers. The dynamic supramolecular interactions and the thermodynamic stability of the host–guest complexes are found to be the crucial factors to drive the sequence control of the supramolecular polymers. Furthermore, the water-soluble supramolecular polymer is red-emissive, which can serve as fluorescent sensor to detect morphine in artificial urine with considerable stability, sensitivity and accuracy. And it can also distinguish heroin and morphine, which are two kinds of opioids with similar structures.

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Binding properties and supramolecular polymerization of a water-soluble resorcin[4]arene

Organic Chemistry Frontiers ◽

10.1039/c9qo00182d ◽

2019 ◽

Vol 6 (8) ◽

pp. 1236-1243 ◽

Cited By ~ 1

Author(s):

Jacobs H. Jordan ◽

Anthony Wishard ◽

Joel T. Mague ◽

Bruce C. Gibb

Keyword(s):

Water Soluble ◽

Supramolecular Polymer ◽

Binding Properties ◽

Supramolecular Polymerization

A ditopic water-soluble resorcinarene is shown to bind salts and undergo self-inclusion to assembly into a supramolecular polymer.

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Supramolecular polymerization of sulfated dendritic peptide amphiphiles into multivalent L-selectin binders

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.17.10 ◽

2021 ◽

Vol 17 ◽

pp. 97-104

Author(s):

David Straßburger ◽

Svenja Herziger ◽

Katharina Huth ◽

Moritz Urschbach ◽

Rainer Haag ◽

...

Keyword(s):

Self Assembly ◽

Supramolecular Polymers ◽

Supramolecular Polymer ◽

Peptide Amphiphile ◽

One Dimensional ◽

Cryogenic Transmission Electron Microscopy ◽

Naturally Occurring ◽

Selectin Ligands ◽

Transmission Electron ◽

Supramolecular Polymerization

The synthesis of a sulfate-modified dendritic peptide amphiphile and its self-assembly into one-dimensional rod-like architectures in aqueous medium is reported. The influence of the ionic strength on the supramolecular polymerization was probed via circular dichroism spectroscopy and cryogenic transmission electron microscopy. Physiological salt concentrations efficiently screen the charges of the dendritic building block equipped with eight sulfate groups and trigger the formation of rigid supramolecular polymers. Since multivalent sulfated supramolecular structures mimic naturally occurring L-selectin ligands, the corresponding affinity was evaluated using a competitive SPR binding assay and benchmarked to an ethylene glycol-decorated supramolecular polymer.

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Oriented arrangement of simple monomers enabled by confinement: towards living supramolecular polymerization

Nature Communications ◽

10.1038/s41467-021-22827-4 ◽

2021 ◽

Vol 12 (1) ◽

Author(s):

Yingtong Zong ◽

Si-Min Xu ◽

Wenying Shi ◽

Chao Lu

Keyword(s):

Activation Barrier ◽

Degree Of Polymerization ◽

Supramolecular Polymer ◽

Energy Principle ◽

Spontaneous Nucleation ◽

Pyrene Derivatives ◽

Multifunctional Molecules ◽

Double Hydroxide ◽

Supramolecular Polymerization ◽

Kinetics Of

AbstractThe living supramolecular polymerization technique provides an exciting research avenue. However, in comparison with the thermodynamic spontaneous nucleation, using simple monomers to realize living supramolecular polymerization is hardly possible from an energy principle. This is because the activation barrier of kinetically trapped simple monomer (nucleation step) is insufficiently high to control the kinetics of subsequent elongation. Here, with the benefit of the confinement from the layered double hydroxide (LDH) nanomaterial, various simple monomers, (such as benzene, naphthalene and pyrene derivatives) successfully form living supramolecular polymer (LSP) with length control and narrow dispersity. The degree of polymerization can reach ~6000. Kinetics studies reveal LDH overcomes a huge energy barrier to inhibit undesired spontaneous nucleation of monomers and disassembly of metastable states. The universality of this strategy will usher exploration into other multifunctional molecules and promote the development of functional LSP.

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Crystallization and near-infrared emission from host–guest based supramolecular polymers

New Journal of Chemistry ◽

10.1039/d1nj01398j ◽

2021 ◽

Author(s):

Wenxia Yin ◽

Lingyi Meng ◽

Tianjun Yu ◽

Jinping Chen ◽

Rui Hu ◽

...

Keyword(s):

Near Infrared ◽

Crystallization Process ◽

Infrared Emission ◽

Supramolecular Polymers ◽

Supramolecular Polymer ◽

Near Infrared Emission

Crystallization process of a NIR emissive supramolecular polymer formed by host–guest complexation of a distyrylanthracene derivative and cucurbiturils is described.

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Supramolecular Systems Containing B–N Frustrated Lewis Pairs of Tris(pentafluorophenyl)borane and Triphenylamine Derivatives

Organic Materials ◽

10.1055/s-0041-1727235 ◽

2021 ◽

Vol 03 (02) ◽

pp. 174-183

Author(s):

P. Chidchob ◽

S. A. H. Jansen ◽

S. C. J. Meskers ◽

E. Weyandt ◽

N. P. van Leest ◽

...

Keyword(s):

Materials Science ◽

Supramolecular Polymers ◽

Frustrated Lewis Pairs ◽

Paramagnetic Resonance ◽

Donor And Acceptor ◽

Donor Acceptor ◽

Noncovalent Polymers ◽

Electron Paramagnetic ◽

Supramolecular Polymerization ◽

Lewis Pairs

The introduction of a chemical additive to supramolecular polymers holds high potential in the development of new structures and functions. In this regard, various donor- and acceptor-based molecules have been applied in the design of these noncovalent polymers. However, the incorporation of boron–nitrogen frustrated Lewis pairs in such architectures is still rare despite their many intriguing properties in catalysis and materials science. The limited choices of suitable boron derivatives represent one of the main limitations for the advancement in this direction. Here, we examine the use of the commercially available tris(pentafluorophenyl)borane with various triphenylamine derivatives to create supramolecular B–N charge transfer systems. Our results highlight the importance of a proper balance between the donor/acceptor strength and the driving force for supramolecular polymerization to achieve stable, long-range ordered B–N systems. Detailed analyses using electron paramagnetic resonance and optical spectroscopy suggest that tris(pentafluorophenyl)borane displays complex behavior with the amide-based triphenylamine supramolecular polymers and may interact in dimers or larger chiral aggregates, depending on the specific structure of the triphenylamines.

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A Water-Soluble Copper-Immobilized Covalent Organic Framework Functioning as an “OFF–ON” Fluorescent Sensor for Amino Acids

Materials Advances ◽

10.1039/d1ma00234a ◽

2021 ◽

Author(s):

Lamiaa Reda Ahmed ◽

Ahmed F. M. EL-Mahdy ◽

Cheng-Tang Pan ◽

Shiao-Wei Kuo

Keyword(s):

Amino Acids ◽

Fluorescent Sensor ◽

Water Soluble ◽

One Pot ◽

Covalent Organic Framework ◽

The One ◽

Organic Framework

In this paper, we describe the construction of a new fluorescent hydroxyl- and hydrazone-based covalent organic framework (TFPB-DHTH COF) through the one-pot polycondensation of 1,3,5-tris(4-formylphenyl)benzene (TFPB) and 2,5-dihydroxyterephthalohydrazide (DHTH) under...

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A phthalocyanine-based fluorescent sensor for Zn2+ ion

Journal of Porphyrins and Phthalocyanines ◽

10.1142/s1088424612501374 ◽

2013 ◽

Vol 17 (01n02) ◽

pp. 99-103 ◽

Cited By ~ 8

Author(s):

Hui He ◽

Jian-Yong Liu ◽

Dennis K.P. Ng

Keyword(s):

Metal Ions ◽

Spectral Properties ◽

Fluorescence Spectra ◽

Near Infrared ◽

Fluorescent Sensor ◽

High Sensitivity ◽

Absorption And Fluorescence Spectra

This paper describes the preparation and spectral properties of a near-infrared fluorophore in which two bis(2-picolyl)amino moieties are axially linked to a silicon(IV) phthalocyanine core. The effects of various metal ions on its absorption and fluorescence spectra have been examined. The results indicate that this compound shows a high sensitivity and moderate selectivity toward Zn2+ ion.

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