Synthesis of a Naphthalimide Functionalized Calix[4]arene; A Host Type Fluorophore for Inclusion Compounds in Organic Medium |
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Authors: | Izilda?A?Bagatin Alexandre?T?Cruz Henrique?E?Toma Mário?J?Politi Email author" target="_blank">Grégoire?J?-F?DemetsEmail author |
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Institution: | (1) Instituto de Química - B12sup. lab 1256/1262-Universidade de São Paulo, Caixa Postal 26077, 05508-000 São Paulo, Brazil;(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 |
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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-calix4]arene and the formation of an inclusion compound in organic medium. This functionalized calix4]arene was conceived as the association of a potential host species with a good fluorophore for optical sensoring purposes. Calix4]-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.in final form: 17 November 2004.This revised version was published online in July 2005 with a corrected issue number. |
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Keywords: | calixarene host-type fluorophore inclusion compound naphthalimide |
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