Issue 2, 2002
From the journal:

Physical Chemistry Chemical Physics

Diffuse reflectance studies of β-phenylpropiophenone and benzophenone inclusion complexes with calix[4], [6] and [8]arenes†

L. F. Vieira Ferreira,*a   M. R. Vieira Ferreira,b   A. S. Oliveira,a   T. J. F. Branco,a   J. V. Pratab  and  J. C. Moreirac  

* Corresponding authors

a Centro de Química-Física Molecular–Complexo Interdisciplinar, Instituto Superior Técnico, Av. Rovisco Pais, Lisboa Codex, Portugal
E-mail: LuisFilipeVF@ist.utl.pt
Fax: 351-21 846 44 55
Tel: 351-21 841 92 52

b Secção de Química Orgânica, Departamento de Engenharia Química, Instituto Superior de Engenharia de Lisboa, R. Conselheiro Emídio Navarro, Lisboa, Portugal

c Centro de Estudos da Saúde do Trabalhador e Ecologia Humana, ENSP, Fundação Oswaldo Cruz, Rua Leopoldo Bulhões 1480, Rio de Janeiro, RJ, Brazil

Abstract

The formation of inclusion complexes of β-phenylpropiophenone and benzophenone with p-tert-butylcalix[4], [6] and [8]arenes (powdered solid samples) was studied with the use of diffuse reflectance techniques. Experimental evidence was obtained for inclusion in all cases. The benzophenone n → π* absorption band exhibits hypsochromic shifts with an increase of the calixarene ring aperture, providing evidence for an increase in cavity polarity. β-Phenylpropiophenone exhibits strong room temperature phosphorescence in contrast to its solution behaviour, and this is a clear evidence for the inclusion of this probe within the calixarene molecules. Calix[4]arene and calix[8]arene provide a more rigid environment to β-phenylpropiophenone whereas calix[6]arene appears to be more flexible. Transient absorption spectra of inclusion complexes with benzophenone (1 : 1 mol : mol, excited at 355 nm) show major triplet formation in the calix[4]arene case, while the ketyl radical of benzophenone is formed in the calix[6]arene case and is predominant in the calix[8]arene case. Phenoxyl radical transient absorption also becomes evident in the last two cases. For β-phenylpropiophenone (1 : 1 mol : mol) phenoxyl radicals are formed but no evidence was found for triplet or ketyl radical formation of this ketone in the calix[4]arene case. However, strong support for the ketyl radical of the aryl alkyl ketone was found for calix[6]arene and calix[8]arene inclusion complexes.

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Article information

DOI
https://doi.org/10.1039/B106760P
Article type
Paper
Submitted
25 Jul 2001
Accepted
19 Sep 2001
First published
05 Dec 2001

Phys. Chem. Chem. Phys., 2002,4, 204-210

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Diffuse reflectance studies of β-phenylpropiophenone and benzophenone inclusion complexes with calix[4], [6] and [8]arenes

L. F. V. Ferreira, M. R. V. Ferreira, A. S. Oliveira, T. J. F. Branco, J. V. Prata and J. C. Moreira, Phys. Chem. Chem. Phys., 2002, 4, 204 DOI: 10.1039/B106760P

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