Issue 27, 2012
From the journal:

Journal of Materials Chemistry

Corroles as anion chemosensors: exploiting their fluorescence behaviour from solution to solid-supported devices†

Carla I. M. Santos,a   Elisabete Oliveira,bc   Joana F. B. Barata,a   M. Amparo F. Faustino,a   José A. S. Cavaleiro,a   M. Graça P. M. S. Neves*a  and  Carlos Lodeiro*bd  

* Corresponding authors

a Chemistry Department and QOPNA, University of Aveiro, Campus Universitário Santiago, 3810-193 Aveiro, Portugal
E-mail: gneves@ua.pt

b BIOSCOPE Group, Faculty of Science, Physical-Chemistry Department, Ourense Campus, University of Vigo, Ourense, Spain
E-mail: clodeiro@uvigo.es

c Veterinary Science Department, (CECAV), University of Trás-os-Montes and Alto Douro, Vila Real, Portugal
E-mail: e.oliveira@uvigo.es

d REQUIMTE-CQFB, Chemistry Department, Faculty of Science and Technology, University NOVA of Lisbon, Monte de Caparica, Portugal
E-mail: cle@fct.unl.pt

Abstract

The reactivity of the new gallium(III) complex of 3-vinyl-5,10,15-tris(pentafluorophenyl)corrole 4, as a diene in Diels–Alder reactions was studied using 1,4-benzoquinone and 1,4-naphthoquinone as dienophiles. In these reactions only the dehydrogenated adducts 5 and 6 were isolated. All the new corrole derivatives 4–6 were fully characterized by elemental analysis, 1H-NMR, 13C-NMR, 19F-NMR, MALDI-TOF-MS, UV-Vis absorption and emission spectroscopy. The sensing ability of compounds 4–6 and of their precursors 1–3 was studied in solution towards the spherical halide ions F−, Cl−, Br−, I−, the linear anion CN− and the bulky anions CH3COO− and H2PO4−. This study was also realized in gas-phase with the anions F− and CN−. A red-shift in the absorption spectra and an enhancement in the emission intensity were observed, with compounds 1, 3 and 5 being strongly sensitive to fluoride. The highest association constant was obtained for 1 with F−, being able to quantify 0.69 ppm of this anion. On the other hand, compounds 1 and 2 present a high sensitivity towards cyanide anions, producing a red-shift in the absorption and emission spectra and an increase in the emission intensity, being able to quantify a minimal amount of 1.43 ppm. Moreover, compounds 1 and 5 were used to prepare two low-cost solid polymers, based on polymethylmethacrylate (PMMA) and polyacrylamide, the last one being very promising since it is able to detect ca. 70.0 ppb of CN− in water. Compounds 2a and 5 were also tested in the presence of 4,4′-bipyridine, caffeine and nicotine and compound 2a proved to be very sensitive to 4,4′-bipyridine, while compound 5 was really effective for detecting caffeine and nicotine.

Graphical abstract: Corroles as anion chemosensors: exploiting their fluorescence behaviour from solution to solid-supported devices

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Article information

DOI
https://doi.org/10.1039/C2JM31281F
Article type
Paper
Submitted
29 Feb 2012
Accepted
08 May 2012
First published
09 May 2012

J. Mater. Chem., 2012,22, 13811-13819

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Corroles as anion chemosensors: exploiting their fluorescence behaviour from solution to solid-supported devices

C. I. M. Santos, E. Oliveira, J. F. B. Barata, M. A. F. Faustino, J. A. S. Cavaleiro, M. G. P. M. S. Neves and C. Lodeiro, J. Mater. Chem., 2012, 22, 13811 DOI: 10.1039/C2JM31281F

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