Concentration-Dependent Self-Assembly of an Unusually Large Hexameric Hydrogen-Bonded Molecular Cage

Severin Merget; Lorenzo Catti; Shani Zev; Dan T. Major; Nils Trapp; Konrad Tiefenbacher

doi:10.1002/chem.202005046

Concentration-Dependent Self-Assembly of an Unusually Large Hexameric Hydrogen-Bonded Molecular Cage

Severin Merget, Lorenzo Catti, Shani Zev, Dan T. Major, Nils Trapp, Konrad Tiefenbacher

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

Abstract

The sizes of available self-assembled hydrogen-bond-based supramolecular capsules and cages are rather limited. The largest systems have volumes of approximately 1400–2300 Å³. Herein, we report a large, hexameric cage based on intermolecular amide–amide dimerization. The unusual structure with openings, reminiscent of covalently linked cages, is held together by 24 hydrogen bonds. With a diameter of 2.3 nm and a cavity volume of ∼2800 Å³, the assembly is larger than any previously known capsule/cage structure relying exclusively on hydrogen bonds. The self-assembly process in chlorinated, organic solvents was found to be strongly concentration dependent, with the monomeric form prevailing at low concentrations. Additionally, the formation of host–guest complexes with fullerenes (C₆₀ and C₇₀) was observed.

Original language	English
Pages (from-to)	4447-4453
Number of pages	7
Journal	Chemistry - A European Journal
Volume	27
Issue number	13
DOIs	https://doi.org/10.1002/chem.202005046
State	Published - 1 Mar 2021

Keywords

amides
fullerenes
host–guest complexes
self-assembly
supramolecular chemistry

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

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10.1002/chem.202005046

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title = "Concentration-Dependent Self-Assembly of an Unusually Large Hexameric Hydrogen-Bonded Molecular Cage",

abstract = "The sizes of available self-assembled hydrogen-bond-based supramolecular capsules and cages are rather limited. The largest systems have volumes of approximately 1400–2300 {\AA}3. Herein, we report a large, hexameric cage based on intermolecular amide–amide dimerization. The unusual structure with openings, reminiscent of covalently linked cages, is held together by 24 hydrogen bonds. With a diameter of 2.3 nm and a cavity volume of ∼2800 {\AA}3, the assembly is larger than any previously known capsule/cage structure relying exclusively on hydrogen bonds. The self-assembly process in chlorinated, organic solvents was found to be strongly concentration dependent, with the monomeric form prevailing at low concentrations. Additionally, the formation of host–guest complexes with fullerenes (C60 and C70) was observed.",

keywords = "amides, fullerenes, host–guest complexes, self-assembly, supramolecular chemistry",

author = "Severin Merget and Lorenzo Catti and Shani Zev and Major, \{Dan T.\} and Nils Trapp and Konrad Tiefenbacher",

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doi = "10.1002/chem.202005046",

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AU - Merget, Severin

AU - Catti, Lorenzo

AU - Zev, Shani

AU - Major, Dan T.

AU - Trapp, Nils

AU - Tiefenbacher, Konrad

PY - 2021/3/1

Y1 - 2021/3/1

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AB - The sizes of available self-assembled hydrogen-bond-based supramolecular capsules and cages are rather limited. The largest systems have volumes of approximately 1400–2300 Å3. Herein, we report a large, hexameric cage based on intermolecular amide–amide dimerization. The unusual structure with openings, reminiscent of covalently linked cages, is held together by 24 hydrogen bonds. With a diameter of 2.3 nm and a cavity volume of ∼2800 Å3, the assembly is larger than any previously known capsule/cage structure relying exclusively on hydrogen bonds. The self-assembly process in chlorinated, organic solvents was found to be strongly concentration dependent, with the monomeric form prevailing at low concentrations. Additionally, the formation of host–guest complexes with fullerenes (C60 and C70) was observed.

KW - amides

KW - fullerenes

KW - host–guest complexes

KW - self-assembly

KW - supramolecular chemistry

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DO - 10.1002/chem.202005046

M3 - مقالة

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SN - 0947-6539

VL - 27

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EP - 4453

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

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ER -

Concentration-Dependent Self-Assembly of an Unusually Large Hexameric Hydrogen-Bonded Molecular Cage

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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