Grafting of benzylic amide macrocycles onto acid-terminated self-assembled monolayers studied by XPS, RAIRS, and contact angle measurements

Francesca Cecchet, Michael Pilling, Laszlo Hevesi, Stefano Schergna, Jenny Wong, Guy Clarkson, David Leigh, Petra Rudolf

Research output: Contribution to journalArticle

Abstract

The grafting of benzylic amide macrocycles, the basic units of more complex mechanically interlocked architectures such as catenanes and rotaxanes, was performed via the functionalization of an acid-terminated self-assembled monolayer (SAM) of 11-mercaptoundecanoic acid (11-MUA). Both chemical and physical adsorption were investigated using macrocycles containing either a reactive hydroxyl functionality or an exopyridyl moiety, with characterization of the systems using X-ray photoelectron spectroscopy (XPS), contact angle measurements, and reflection absorption infrared spectroscopy (RAIRS). By comparing theoretical values with experimental data, it was found that up to 40% of the acid groups on the SAM surface were modified by the macrocycles and that the macrocycle coverage can be controlled by varying the reaction time. Stability tests demonstrated that the prepared films are stable in air, under ultrasound treatment and against chemical substitution. RAIRS measurements suggested a tilted orientation of the macrocycle with respect to the plane of the SAM surface.
Original languageEnglish
Pages (from-to)10863-10872
Number of pages10
JournalJournal of physical chemistry B
Volume107
Publication statusPublished - 2003

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Self assembled monolayers
Angle measurement
Absorption spectroscopy
Amides
Contact angle
Infrared spectroscopy
X ray photoelectron spectroscopy
Acids
Substitution reactions
Ultrasonics
Adsorption
Air

Cite this

Cecchet, Francesca ; Pilling, Michael ; Hevesi, Laszlo ; Schergna, Stefano ; Wong, Jenny ; Clarkson, Guy ; Leigh, David ; Rudolf, Petra. / Grafting of benzylic amide macrocycles onto acid-terminated self-assembled monolayers studied by XPS, RAIRS, and contact angle measurements. In: Journal of physical chemistry B. 2003 ; Vol. 107. pp. 10863-10872.
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abstract = "The grafting of benzylic amide macrocycles, the basic units of more complex mechanically interlocked architectures such as catenanes and rotaxanes, was performed via the functionalization of an acid-terminated self-assembled monolayer (SAM) of 11-mercaptoundecanoic acid (11-MUA). Both chemical and physical adsorption were investigated using macrocycles containing either a reactive hydroxyl functionality or an exopyridyl moiety, with characterization of the systems using X-ray photoelectron spectroscopy (XPS), contact angle measurements, and reflection absorption infrared spectroscopy (RAIRS). By comparing theoretical values with experimental data, it was found that up to 40{\%} of the acid groups on the SAM surface were modified by the macrocycles and that the macrocycle coverage can be controlled by varying the reaction time. Stability tests demonstrated that the prepared films are stable in air, under ultrasound treatment and against chemical substitution. RAIRS measurements suggested a tilted orientation of the macrocycle with respect to the plane of the SAM surface.",
author = "Francesca Cecchet and Michael Pilling and Laszlo Hevesi and Stefano Schergna and Jenny Wong and Guy Clarkson and David Leigh and Petra Rudolf",
year = "2003",
language = "English",
volume = "107",
pages = "10863--10872",
journal = "Journal of physical chemistry B",
issn = "1089-5647",
publisher = "American Chemical Society",

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Grafting of benzylic amide macrocycles onto acid-terminated self-assembled monolayers studied by XPS, RAIRS, and contact angle measurements. / Cecchet, Francesca; Pilling, Michael; Hevesi, Laszlo; Schergna, Stefano; Wong, Jenny; Clarkson, Guy; Leigh, David; Rudolf, Petra.

In: Journal of physical chemistry B, Vol. 107, 2003, p. 10863-10872.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Grafting of benzylic amide macrocycles onto acid-terminated self-assembled monolayers studied by XPS, RAIRS, and contact angle measurements

AU - Cecchet, Francesca

AU - Pilling, Michael

AU - Hevesi, Laszlo

AU - Schergna, Stefano

AU - Wong, Jenny

AU - Clarkson, Guy

AU - Leigh, David

AU - Rudolf, Petra

PY - 2003

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N2 - The grafting of benzylic amide macrocycles, the basic units of more complex mechanically interlocked architectures such as catenanes and rotaxanes, was performed via the functionalization of an acid-terminated self-assembled monolayer (SAM) of 11-mercaptoundecanoic acid (11-MUA). Both chemical and physical adsorption were investigated using macrocycles containing either a reactive hydroxyl functionality or an exopyridyl moiety, with characterization of the systems using X-ray photoelectron spectroscopy (XPS), contact angle measurements, and reflection absorption infrared spectroscopy (RAIRS). By comparing theoretical values with experimental data, it was found that up to 40% of the acid groups on the SAM surface were modified by the macrocycles and that the macrocycle coverage can be controlled by varying the reaction time. Stability tests demonstrated that the prepared films are stable in air, under ultrasound treatment and against chemical substitution. RAIRS measurements suggested a tilted orientation of the macrocycle with respect to the plane of the SAM surface.

AB - The grafting of benzylic amide macrocycles, the basic units of more complex mechanically interlocked architectures such as catenanes and rotaxanes, was performed via the functionalization of an acid-terminated self-assembled monolayer (SAM) of 11-mercaptoundecanoic acid (11-MUA). Both chemical and physical adsorption were investigated using macrocycles containing either a reactive hydroxyl functionality or an exopyridyl moiety, with characterization of the systems using X-ray photoelectron spectroscopy (XPS), contact angle measurements, and reflection absorption infrared spectroscopy (RAIRS). By comparing theoretical values with experimental data, it was found that up to 40% of the acid groups on the SAM surface were modified by the macrocycles and that the macrocycle coverage can be controlled by varying the reaction time. Stability tests demonstrated that the prepared films are stable in air, under ultrasound treatment and against chemical substitution. RAIRS measurements suggested a tilted orientation of the macrocycle with respect to the plane of the SAM surface.

M3 - Article

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JO - Journal of physical chemistry B

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