Supramolecular motifs for the self-assembly of monosubstituted pillar[5]arenes with an amide fragment: from nanoparticles to supramolecular polymers

2018 ◽  
Vol 42 (24) ◽  
pp. 19853-19863 ◽  
Author(s):  
A. A. Nazarova ◽  
P. L. Padnya ◽  
A. I. Gilyazeva ◽  
A. A. Khannanov ◽  
V. G. Evtugyn ◽  
...  
Keyword(s):  
Self Assembly ◽  
The Self ◽  
Supramolecular Polymers ◽  
Supramolecular Motifs ◽  
Amide Fragment

The effects of solvents on the aggregation properties of novel monosubstituted pillar[5]arenes containing an N-alkylamide fragment have been investigated.

scholarly journals Living supramolecular polymerization of fluorinated cyclohexanes

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Oleksandr Shyshov ◽  
Shyamkumar Vadakket Haridas ◽  
Luca Pesce ◽  
Haoyuan Qi ◽  
Andrea Gardin ◽  
...  
Keyword(s):  
Dipole Moment ◽  
Self Assembly ◽  
Materials Science ◽  
Helical Structure ◽  
The Self ◽  
Supramolecular Polymers ◽  
Aliphatic Compound ◽  
Double Helical Structure ◽  
Key Driver ◽  
Supramolecular Polymerization

AbstractThe development of powerful methods for living covalent polymerization has been a key driver of progress in organic materials science. While there have been remarkable reports on living supramolecular polymerization recently, the scope of monomers is still narrow and a simple solution to the problem is elusive. Here we report a minimalistic molecular platform for living supramolecular polymerization that is based on the unique structure of all-cis 1,2,3,4,5,6-hexafluorocyclohexane, the most polar aliphatic compound reported to date. We use this large dipole moment (6.2 Debye) not only to thermodynamically drive the self-assembly of supramolecular polymers, but also to generate kinetically trapped monomeric states. Upon addition of well-defined seeds, we observed that the dormant monomers engage in a kinetically controlled supramolecular polymerization. The obtained nanofibers have an unusual double helical structure and their length can be controlled by the ratio between seeds and monomers. The successful preparation of supramolecular block copolymers demonstrates the versatility of the approach.

The construction of rigid supramolecular polymers in water through the self-assembly of rod-like monomers and cucurbit[8]uril

2014 ◽  
Vol 50 (59) ◽  
pp. 7982-7985 ◽  
Author(s):  
Feng Lin ◽  
Tian-Guang Zhan ◽  
Tian-You Zhou ◽  
Kang-Da Zhang ◽  
Guang-Yu Li ◽  
...  
Keyword(s):  
Self Assembly ◽  
The Self ◽  
Supramolecular Polymers

Two types of stick-like supramolecular polymers possessing rigid backbones have been fabricated through the self-assembly of rod-like monomers and cucurbit[8]uril in water.

Switchable Supramolecular Polymers from the Self-Assembly of a Small Monomer with Two Orthogonal Binding Interactions

2011 ◽  
Vol 133 (23) ◽  
pp. 8961-8971 ◽  
Author(s):  
Gerd Gröger ◽  
Wolfgang Meyer-Zaika ◽  
Christoph Böttcher ◽  
Franziska Gröhn ◽  
Christian Ruthard ◽  
...  
Keyword(s):  
Self Assembly ◽  
The Self ◽  
Supramolecular Polymers ◽  
Binding Interactions

Planarization of tetracarboxamides: tuning the self-assembly of polycyclic aromatic hydrocarbons

2019 ◽  
Vol 55 (43) ◽  
pp. 6070-6073
Author(s):  
Yeray Dorca ◽  
Cristina Naranjo ◽  
Patricia Delgado-Martínez ◽  
Rafael Gómez ◽  
Luis Sánchez
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Aromatic Hydrocarbons ◽  
Self Assembly ◽  
Supramolecular Structures ◽  
The Self ◽  
Supramolecular Polymers ◽  
Self Assembling ◽  
Π Stacking ◽  
Polycyclic Aromatic

The geometry-dependent self-assembling features of two PAHs, 1 and 2, is reported. The more planar 1 forms H-type supramolecular polymers, in a highly cooperative fashion by combination of H-bonding and π-stacking, with rod-like morphology. However, the highly distorted 2 interacts only by means of H-bonding yielding lamellar supramolecular structures.

Synthesis of dynamic imine macrocyclic supramolecular polymers via synchronized self-assembly based on dynamic covalent bonds and noncovalent interactions

2020 ◽  
Vol 56 (65) ◽  
pp. 9288-9291 ◽  
Author(s):  
Zhenfeng He ◽  
Yufeng Huo ◽  
Chao Wang ◽  
Duo Pan ◽  
Binbin Dong ◽  
...  
Keyword(s):  
Self Assembly ◽  
Noncovalent Interactions ◽  
Single Step ◽  
The Self ◽  
Supramolecular Polymers ◽  
Aggregation Process ◽  
Covalent Bonds

The preparation of host imine macrocycles and the self-assembly aggregation process are merged into one single step for self-assembly to form dynamic imine macrocyclic supramolecular polymers.

scholarly journals Unconventional Chiral Amplification in Luminescent Supramolecular Polymers Based on Trisbiphenylamine-tricarboxamides

2020 ◽  
Vol 02 (01) ◽  
pp. 041-046 ◽  
Author(s):  
Yeray Dorca ◽  
Cristina Naranjo ◽  
Goutam Ghosh ◽  
Rafael Gómez ◽  
Gustavo Fernández ◽  
...  
Keyword(s):  
Self Assembly ◽  
The Self ◽  
Supramolecular Polymers ◽  
Side Chains ◽  
Chiral Amplification ◽  
Supramolecular Polymerization ◽  
Efficient Transfer

We describe the synthesis of two propeller-shaped, emissive trisbiphenylamines 1 and (S)-2. Whilst achiral 1 forms supramolecular polymers following a cooperative mechanism, the self-assembly of chiral (S)-2 can be described by an isodesmic mechanism. Despite the isodesmic character of the supramolecular polymerization of (S)-2, an efficient transfer of chirality from the embedded point chirality of the peripheral side chains to the aggregates is demonstrated. The co-assembly of 1 and (S)-2 in a sergeants-and-soldiers experiment shows a very different dichroic response to that registered for pristine (S)-2, with a copolymerization curve displaying two transitions. Both these transitions coincide with those observed for the pristine achiral and chiral components, thus suggesting a self-sorting effect.

The solvent nature influence on the self-assembly of monosubstituted pillar[5]arenes containing N-(aminoalkyl)amide fragment

2020 ◽  
Vol 63 (7) ◽  
pp. 1-10
Author(s):  
Anastasia A. Nazarova ◽  
◽  
Alsu I. Gilyazeva ◽  
Ivan I. Stoykov ◽  
◽  
...  
Keyword(s):  
Inclusion Complexes ◽  
Self Assembly ◽  
Electrostatic Interactions ◽  
Supramolecular Polymers ◽  
Hydrodynamic Diameter ◽  
Covalent Bonds ◽  
Interlocked Molecules ◽  
Intramolecular Hydrogen ◽  
Amide Fragment ◽  
Average Hydrodynamic Diameter

Chemistry of macrocyclic compounds is one of the rapidly developing areas of modern organic chemistry. These macrocycles have become widespread due to the high availability of parents compounds, the possibility of synthesis of ligands based on them for highly selective recognition, ion-selective membranes, electrodes, sensors and nanocontainers for targeted drug delivery. Moreover, in the past few years, attention of researchers has again been riveted on mechanically interlocked molecules (rotaxanes and pseudorotaxans) and supramolecular polymers, which can be explained by their potential application as molecular machines and materials. Mechanically interlocked molecules are molecular architectures consisting from two or more components which mechanically bind due to their own topology. Supramolecular polymers are comprise ordered monomer units combined via non-covalent bonds (hydrogen bonds or electrostatic interactions). Thus, this manuscript presents an approach to the synthesis of monosubstituted pillar[5]arenes containing N-(aminoalkyl)amide fragments with various substituent lengths. The formation of self-inclusion complexes by synthesized macrocycles was established by one- and two-dimensional NMR spectroscopy. According to NMR data, only four carbon atoms of the alkyl fragment were included in the macrocyclic cavity regardless of the alkyl chain length. Formation of self-inclusion complexes becomes possible due to the intramolecular hydrogen bond between the NH protons and the oxygen atom of methoxyl fragment, which is confirmed by IR spectroscopy. It was shown by dynamic light scattering that the synthesized pillar[5]arenes in chloroform form aggregates with an average hydrodynamic diameter of 316-640 nm and polydispersity index from 0.18 to 0.20, while polydisperse systems are formed in dimethyl sulfoxide.

Understanding the self-assembly of amino ester-based benzene-1,3,5-tricarboxamides using molecular dynamics simulations

2017 ◽  
Vol 19 (1) ◽  
pp. 258-266 ◽  
Author(s):  
Karteek K. Bejagam ◽  
Richard C. Remsing ◽  
Michael L. Klein ◽  
Sundaram Balasubramanian
Keyword(s):  
Molecular Dynamics ◽  
Molecular Dynamics Simulations ◽  
Self Assembly ◽  
The Self ◽  
Supramolecular Polymers ◽  
Amino Ester ◽  
Dynamics Simulations ◽  
Hydrogen Bonded

Amino ester-based benzene-1,3,5-tricarboxamides (BTAs) are widely studied experimentally for their facile self-assembly, which leads to strong three-fold hydrogen bonded supramolecular polymers.

Helical Porous Protein Mimics Self-Assembled from Amphiphilic Dendritic Dipeptides

2005 ◽  
Vol 58 (6) ◽  
pp. 472 ◽  
Author(s):  
Virgil Percec ◽  
Andrés Dulcey ◽  
Mihai Peterca ◽  
Monica Ilies ◽  
Yoshiko Miura ◽  
...  
Keyword(s):  
Self Assembly ◽  
Transmembrane Proteins ◽  
Supramolecular Assemblies ◽  
The Self ◽  
Supramolecular Polymers ◽  
Protein Mimics ◽  
New Class ◽  
Solid States ◽  
Self Assembled

This manuscript reports the synthesis and the self-assembly of (4-3,4,5-3,5)nG2-CH2-Boc-l-Tyr-l-Ala-OMe dendritic dipeptides (n = 12, 16). These dendritic dipeptides self-assemble both in solution and in solid states into helical porous supramolecular columns that mimic porous transmembrane proteins. These supramolecular assemblies provide also a new class of tubular supramolecular polymers.

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