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Design, Synthesis and Aggregation of Amphiphilic Monomers—Cyclic and Tubular Hydrogen-Bonded Self-assembly in Conventional and Polar Media

Lidskog, Anna LU ; Neniškis, Algirdas ; Edin, Simon LU ; Takács, Zoltán LU ; Klimkevičius, Vaidas ; Orentas, Edvinas and Wärnmark, Kenneth LU (2025) In Chemistry - A European Journal
Abstract

Two hydrogen-bonding monomers containing tetraethylene glycol (TEG) chains have been synthesized and characterized. The monomers are based on a bicyclic scaffold appended with either 4H-bonding benzyl-substituted ureidopyrimidinone motifs or 2H-bonding unsubstituted pyrrole-fused ureidopyrimidinone motifs, with the TEG chains introduced with the aim of developing amphiphilic monomers soluble in nonpolar and polar organic solvents in order to extend the utility of H-bonding in supramolecular chemistry. In CDCl3, both monomers formed cyclic tetramers. The monomer containing 2H-bonding motifs was found to form significantly less-stable aggregates than its previously reported alkylated analogue, most likely due to interference... (More)

Two hydrogen-bonding monomers containing tetraethylene glycol (TEG) chains have been synthesized and characterized. The monomers are based on a bicyclic scaffold appended with either 4H-bonding benzyl-substituted ureidopyrimidinone motifs or 2H-bonding unsubstituted pyrrole-fused ureidopyrimidinone motifs, with the TEG chains introduced with the aim of developing amphiphilic monomers soluble in nonpolar and polar organic solvents in order to extend the utility of H-bonding in supramolecular chemistry. In CDCl3, both monomers formed cyclic tetramers. The monomer containing 2H-bonding motifs was found to form significantly less-stable aggregates than its previously reported alkylated analogue, most likely due to interference from the TEG chains. Despite the weaker aggregation, the 2H-bonded tetramers were able to stack into tubular polymers through orthogonal H-bonding in less polar solvent (toluene) or when a suitable guest (C70) was introduced. Comparison of the TEGylated monomers with previously reported alkylated analogues showed that the introduction of TEG chains resulted in increased solubility in a wide range of solvents. By using one of the TEGylated monomers, nonpolar C60 could be solubilized in polar solvent acetonitrile by forming an inclusion complex. This complex was used as a homogeneous catalyst for photochemical oxidation of sulfides to sulfoxides in acetonitrile.

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author
; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
in press
subject
keywords
Cyclic receptors, fullerene, hydrogen bonding, oligoethylene groups, photooxidation
in
Chemistry - A European Journal
publisher
Wiley-Blackwell
external identifiers
  • scopus:105023976997
  • pmid:41351203
ISSN
0947-6539
DOI
10.1002/chem.202502804
language
English
LU publication?
yes
additional info
Publisher Copyright: © 2025 Wiley-VCH GmbH.
id
f2082ce3-9354-4cb1-9207-9bfe4daaaa16
date added to LUP
2026-03-03 15:28:30
date last changed
2026-03-04 03:00:03
@article{f2082ce3-9354-4cb1-9207-9bfe4daaaa16,
  abstract     = {{<p>Two hydrogen-bonding monomers containing tetraethylene glycol (TEG) chains have been synthesized and characterized. The monomers are based on a bicyclic scaffold appended with either 4H-bonding benzyl-substituted ureidopyrimidinone motifs or 2H-bonding unsubstituted pyrrole-fused ureidopyrimidinone motifs, with the TEG chains introduced with the aim of developing amphiphilic monomers soluble in nonpolar and polar organic solvents in order to extend the utility of H-bonding in supramolecular chemistry. In CDCl<sub>3</sub>, both monomers formed cyclic tetramers. The monomer containing 2H-bonding motifs was found to form significantly less-stable aggregates than its previously reported alkylated analogue, most likely due to interference from the TEG chains. Despite the weaker aggregation, the 2H-bonded tetramers were able to stack into tubular polymers through orthogonal H-bonding in less polar solvent (toluene) or when a suitable guest (C<sub>70</sub>) was introduced. Comparison of the TEGylated monomers with previously reported alkylated analogues showed that the introduction of TEG chains resulted in increased solubility in a wide range of solvents. By using one of the TEGylated monomers, nonpolar C<sub>60</sub> could be solubilized in polar solvent acetonitrile by forming an inclusion complex. This complex was used as a homogeneous catalyst for photochemical oxidation of sulfides to sulfoxides in acetonitrile.</p>}},
  author       = {{Lidskog, Anna and Neniškis, Algirdas and Edin, Simon and Takács, Zoltán and Klimkevičius, Vaidas and Orentas, Edvinas and Wärnmark, Kenneth}},
  issn         = {{0947-6539}},
  keywords     = {{Cyclic receptors; fullerene; hydrogen bonding; oligoethylene groups; photooxidation}},
  language     = {{eng}},
  publisher    = {{Wiley-Blackwell}},
  series       = {{Chemistry - A European Journal}},
  title        = {{Design, Synthesis and Aggregation of Amphiphilic Monomers—Cyclic and Tubular Hydrogen-Bonded Self-assembly in Conventional and Polar Media}},
  url          = {{http://dx.doi.org/10.1002/chem.202502804}},
  doi          = {{10.1002/chem.202502804}},
  year         = {{2025}},
}