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Synthesis of a Naphthalimide Functionalized Calix[4]arene; A Host Type Fluorophore for Inclusion Compounds in Organic Medium

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Abstract

This article reports the synthesis and the properties of 5,11,17,23-tetra(t-butyl)-25,27-bis-(ethoxy-1,8-naphthalimide)-26,28-hidroxy-calix[4]arene and the formation of an inclusion compound in organic medium. This functionalized calix[4]arene was conceived as the association of a potential host species with a good fluorophore for optical sensoring purposes. Calix[4]-NI as we will call it, maintains its ‘cone-pinched’ configuration and exhibits typical naphthalimide fluorescence bands in non-polar solvents. Its ability to interact with guest species via hydrogen bonding in its endo-hydrophilic cavity to form inclusion compounds was verified with absorption and fluorescence measurements using N-ethanol-1,8-naphthalimide as guest species, which was projected to fit exactly the host cavity and to interact with its naphthalimide π electrons. For this reason, it was possible to follow the formation of the inclusion compound with electronic spectroscopy.

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Authors and Affiliations

  1. Instituto de Química - B12sup. lab 1256/1262-Universidade de São Paulo, Caixa Postal 26077, 05508-000, São Paulo, Brazil

    Izilda A. Bagatin, Alexandre T. Cruz, Henrique E. Toma & Mário J. Politi

  2. Departamento de Química -F.F.C.L.R.P., Universidade de São Paulo, Av. dos Bandeirantes 3900, 14040-901, Ribeirão Preto, S.P., Brazil

    Grégoire J. -F. Demets

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  1. Izilda A. Bagatin
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  2. Alexandre T. Cruz
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  3. Henrique E. Toma
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  4. Mário J. Politi
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  5. Grégoire J. -F. Demets
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Correspondence to Grégoire J. -F. Demets.

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in final form: 17 November 2004.

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Bagatin, I.A., Cruz, A.T., Toma, H.E. et al. Synthesis of a Naphthalimide Functionalized Calix[4]arene; A Host Type Fluorophore for Inclusion Compounds in Organic Medium. J Incl Phenom Macrocycl Chem 52, 189–193 (2005). https://doi.org/10.1007/s10847-004-6385-2

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