Issue 10, 2011
From the journal:

Physical Chemistry Chemical Physics

Surface grafting and reactivity of calixarene-based receptors and pseudorotaxanes on Si(100)†

Alice Boccia,a   Valeria Lanzilotto,a   Robertino Zanoni,*a   Luca Pescatori,b   Arturo Arduinib  and  Andrea Secchi*b  

* Corresponding authors

a Dipartimento di Chimica, Università degli Studi di Roma ‘La Sapienza’, p.le Aldo Moro 5, I-00185 Roma, Italy
E-mail: robertino.zanoni@uniroma1.it
Fax: +39 06 490324
Tel: +39 06 49913328

b Dipartimento di Chimica Organica e Industriale and Unità INSTM Sez. 4-UdR Parma, Università di Parma, Parco Area delle Scienze 17/a, I-43124 Parma, Italy
E-mail: andrea.secchi@unipr.it
Fax: +39 0521 905472
Tel: +39 0521 905409

Abstract

The first report is given here on the anchoring on H–Si(100) of calix[4]arenes and calix[6]arene-based pseudorotaxanes, versatile building blocks for molecular devices. Covalent functionalization on Si was reached through a wet chemistry recipe, by making use of an extra-mild photochemical activation via visible light of C[double bond, length as m-dash]C terminated anchoring arms. Our approach largely preserves the integrity of the molecular substrate, also allowing for a full monolayer of pseudorotaxane to be formed on Si(100). Molecular adhesion has been demonstrated by the presence and quantitation of XPS signals from specific elements in the molecules. AFM measurements performed on Si(100)/calix[4]arenes have revealed structures 2.3 nm high, consistent with the length of the molecule. The availability of the calix[4]arene cavity to host further species after anchoring on Si has been demonstrated by the successful complexation reaction with Cs+ ions, resulting in a 1 ∶ 1 calix/Cs+ ratio, and with N-methyl pyridinium iodide. A pseudorotaxane species, composed of a calix[6]arene wheel derivatised with N-phenylureido groups on the upper rim and a viologen (4,4′-bipyridinium) containing axle, has been anchored on Si(100) via the C[double bond, length as m-dash]C termination of the axle. We demonstrated the self-assembling of this pseudorotaxane covalently bound by use of XPS.

Graphical abstract: Surface grafting and reactivity of calixarene-based receptors and pseudorotaxanes on Si(100)

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Article information

DOI
https://doi.org/10.1039/C0CP01916J
Article type
Paper
Submitted
23 Sep 2010
Accepted
13 Dec 2010
First published
24 Jan 2011

Phys. Chem. Chem. Phys., 2011,13, 4444-4451

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Surface grafting and reactivity of calixarene-based receptors and pseudorotaxanes on Si(100)

A. Boccia, V. Lanzilotto, R. Zanoni, L. Pescatori, A. Arduini and A. Secchi, Phys. Chem. Chem. Phys., 2011, 13, 4444 DOI: 10.1039/C0CP01916J

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