Supramolecular polymerisation in water; elucidating the role of hydrophobic and hydrogen-bond interactions

Christianus M. A. Leenders; Matthew B. Baker; Imke A. B. Pijpers; Rene P. M. Lafleur; Lorenzo Albertazzi; Anja R. A. Palmans; E. W. Meijer

doi:10.1039/c5sm02843d

Supramolecular polymerisation in water; elucidating the role of hydrophobic and hydrogen-bond interactions

Christianus M. A. Leenders, Matthew B. Baker, Imke A. B. Pijpers, Rene P. M. Lafleur, Lorenzo Albertazzi, Anja R. A. Palmans^*, E. W. Meijer^*

^*Corresponding author for this work

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

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Abstract

Understanding the self-assembly of small molecules in water is crucial for the development of responsive, biocompatible soft materials. Here, a family of benzene-1,3,5-tricarboxamide (BTA) derivatives that comprise a BTA moiety connected to an amphiphilic chain is synthesised with the aim to elucidate the role of hydrophobic and hydrogen-bonding interactions in the self-assembly of these BTAs. The amphiphilic chain consists of an alkyl chain with a length of 10, 11, or 12 methylene units, connected to a tetraethylene glycol (at the periphery). The results show that an undecyl spacer is the minimum length required for these BTAs to self-assemble into supramolecular polymers. Interestingly, exchange studies reveal only minor differences in exchange rates between BTAs containing undecyl or dodecyl spacers. Additionally, IR spectroscopy provides the first experimental evidence that hydrogen-bonding is operative and contributes to the stabilisation of the supramolecular polymers in water.

Original language	English
Pages (from-to)	2887-2893
Journal	Soft Matter
Volume	12
Issue number	11
DOIs	https://doi.org/10.1039/c5sm02843d
Publication status	Published - 2016

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10.1039/c5sm02843d

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Cite this

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title = "Supramolecular polymerisation in water; elucidating the role of hydrophobic and hydrogen-bond interactions",

abstract = "Understanding the self-assembly of small molecules in water is crucial for the development of responsive, biocompatible soft materials. Here, a family of benzene-1,3,5-tricarboxamide (BTA) derivatives that comprise a BTA moiety connected to an amphiphilic chain is synthesised with the aim to elucidate the role of hydrophobic and hydrogen-bonding interactions in the self-assembly of these BTAs. The amphiphilic chain consists of an alkyl chain with a length of 10, 11, or 12 methylene units, connected to a tetraethylene glycol (at the periphery). The results show that an undecyl spacer is the minimum length required for these BTAs to self-assemble into supramolecular polymers. Interestingly, exchange studies reveal only minor differences in exchange rates between BTAs containing undecyl or dodecyl spacers. Additionally, IR spectroscopy provides the first experimental evidence that hydrogen-bonding is operative and contributes to the stabilisation of the supramolecular polymers in water.",

author = "Leenders, {Christianus M. A.} and Baker, {Matthew B.} and Pijpers, {Imke A. B.} and Lafleur, {Rene P. M.} and Lorenzo Albertazzi and Palmans, {Anja R. A.} and Meijer, {E. W.}",

year = "2016",

doi = "10.1039/c5sm02843d",

language = "English",

volume = "12",

pages = "2887--2893",

journal = "Soft Matter",

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publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Supramolecular polymerisation in water; elucidating the role of hydrophobic and hydrogen-bond interactions

AU - Leenders, Christianus M. A.

AU - Baker, Matthew B.

AU - Pijpers, Imke A. B.

AU - Lafleur, Rene P. M.

AU - Albertazzi, Lorenzo

AU - Palmans, Anja R. A.

AU - Meijer, E. W.

PY - 2016

Y1 - 2016

N2 - Understanding the self-assembly of small molecules in water is crucial for the development of responsive, biocompatible soft materials. Here, a family of benzene-1,3,5-tricarboxamide (BTA) derivatives that comprise a BTA moiety connected to an amphiphilic chain is synthesised with the aim to elucidate the role of hydrophobic and hydrogen-bonding interactions in the self-assembly of these BTAs. The amphiphilic chain consists of an alkyl chain with a length of 10, 11, or 12 methylene units, connected to a tetraethylene glycol (at the periphery). The results show that an undecyl spacer is the minimum length required for these BTAs to self-assemble into supramolecular polymers. Interestingly, exchange studies reveal only minor differences in exchange rates between BTAs containing undecyl or dodecyl spacers. Additionally, IR spectroscopy provides the first experimental evidence that hydrogen-bonding is operative and contributes to the stabilisation of the supramolecular polymers in water.

AB - Understanding the self-assembly of small molecules in water is crucial for the development of responsive, biocompatible soft materials. Here, a family of benzene-1,3,5-tricarboxamide (BTA) derivatives that comprise a BTA moiety connected to an amphiphilic chain is synthesised with the aim to elucidate the role of hydrophobic and hydrogen-bonding interactions in the self-assembly of these BTAs. The amphiphilic chain consists of an alkyl chain with a length of 10, 11, or 12 methylene units, connected to a tetraethylene glycol (at the periphery). The results show that an undecyl spacer is the minimum length required for these BTAs to self-assemble into supramolecular polymers. Interestingly, exchange studies reveal only minor differences in exchange rates between BTAs containing undecyl or dodecyl spacers. Additionally, IR spectroscopy provides the first experimental evidence that hydrogen-bonding is operative and contributes to the stabilisation of the supramolecular polymers in water.

U2 - 10.1039/c5sm02843d

DO - 10.1039/c5sm02843d

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VL - 12

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JO - Soft Matter

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