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

Santos, Carla I. M.; Oliveira, Elisabete; Barata, Joana F. B.; Faustino, Maria A. F.; Cavaleiro, José A. S.; Neves, Maria G. P. M. S.; Lodeiro, Carlos

doi:10.1039/c2jm31281f

Cited by 83 publications

(42 citation statements)

References 24 publications

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“…From the porphyrinoid family, corroles have merited special attention in recent years because of their high fluorescence quantum yields and high molar extinction coefficients; moreover, the corrole core can accommodate different metal ions that can act as active centers. In experiments performed in toluene, the sensing abilities of probes 146 – 151 towards a range of biologically and environmentally relevant anions have been studied (Figure ) . Spherical (F − , Br − , and Cl − ) and linear (CN − ) anions have been investigated; bulky anions such as CH 3 COO − and H 2 PO 4 − have also been studied.…”

Section: Red Fluorescent Dyesmentioning

confidence: 99%

Green and Red Fluorescent Dyes for Translational Applications in Imaging and Sensing Analytes: A Dual‐Color Flag

et al. 2017

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Red and green are two of the most‐preferred colors from the entire chromatic spectrum, and red and green dyes are widely used in biochemistry, immunohistochemistry, immune‐staining, and nanochemistry applications. Selective dyes with green and red excitable chromophores can be used in biological environments, such as tissues and cells, and can be irradiated with visible light without cell damage. This critical review, covering a period of five years, provides an overview of the most‐relevant results on the use of red and green fluorescent dyes in the fields of bio‐, chemo‐ and nanoscience. The review focuses on fluorescent dyes containing chromophores such as fluorescein, rhodamine, cyanine, boron–dipyrromethene (BODIPY), 7‐nitobenz‐2‐oxa‐1,3‐diazole‐4‐yl, naphthalimide, acridine orange, perylene diimides, coumarins, rosamine, Nile red, naphthalene diimide, distyrylpyridinium, benzophosphole P‐oxide, benzoresorufins, and tetrapyrrolic macrocycles. Metal complexes and nanomaterials with these dyes are also discussed.

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Section: Red Fluorescent Dyesmentioning

confidence: 99%

Green and Red Fluorescent Dyes for Translational Applications in Imaging and Sensing Analytes: A Dual‐Color Flag

et al. 2017

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“…Amines and polyamines, 154 calix-pyrroles, 155 subphthalocyanines, 156 Cors, 157 and Pors 158 are used to create anion receptors. Anion recognition involves the NH groups of the pyrrole units in Pors.…”

Section: Substituted Fluorinated Porphyrinoids For Application In Matmentioning

confidence: 99%

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

et al. 2016

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Porphyrinoids are robust heterocyclic dyes studied extensively for their applications in medicine and as photonic materials because of their tunable photophysical properties, diverse means of modifying the periphery, and the ability to chelate most transition metals. Commercial applications include their use as phthalocyanine dyes in optical discs, porphyrins in photodynamic therapy, and as oxygen sensors. Most applications of these dyes require exocyclic moieties to improve solubility, target diseases, modulate photophysical properties, or direct the self-organization into architectures with desired photonic properties. The synthesis of the porphyrinoid depends on the desired application, but the de novo synthesis often involves several steps, is time consuming, and results in low isolated yields. Thus, the application of core porphyrinoid platforms that can be rapidly and efficiently modified to evaluate new molecular architectures allows researchers to focus on the design concepts rather than the synthesis methods, and opens porphyrinoid chemistry to a broader scientific community. We have focused on several widely available, commercially viable porphyrinoids as platforms: meso-perfluorophenylporphyrin, perfluoro-phthalocyanine, and meso-perfluorophenylcorrole. The perfluorophenylporphyrin is readily converted to the chlorin, bacteriochlorin, and isobacteriochlorin. Derivatives of all six of these core platforms can be efficiently and controllably made via mild nucleophilic aromatic substitution reactions using primary S, N, and O nucleophiles bearing a wide variety of functional groups. The remaining fluoro groups enhance the photo and oxidative stability of the dyes and can serve as spectroscopic signatures to characterize the compounds or in imaging applications using 19F NMR. This review provides an overview of the chemistry of fluorinated porphyrinoids that are being used as a platform to create libraries of photo-active compounds for applications in medicine and materials.

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“…[18] Concerning our studies on structural modification of mesotetraarylporphyrins at their b-pyrrolic positions, namely through a formyl group, [19] we report here an efficient and facile access to a new 3,5-di-substituted pyridine bearing two porphyrin-2-ylmethyl moieties (2) from 2-formyl-5,10,15,20tetraphenylporphyrin (1). Based on the ability of porphyrins to be used as fluorescent and colorimetric chemosensors and also on our research interest on this topic [20][21][22][23][24][25] we envisaged that the presence of the two porphyrinic units linked by the pyridine could potentiate the ability of the new system to recognize and to bind different metal ions.…”

Section: Introductionmentioning

confidence: 99%

A New 3,5‐Bisporphyrinylpyridine Derivative as a Fluorescent Ratiometric Probe for Zinc Ions

Moura

Núñez

Santos

et al. 2014

Chemistry A European J

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A new 3,5-disubstituted pyridine with two porphyrin moieties was prepared through an efficient synthetic approach involving 2-formyl-5,10,15,20-tetraphenylporphyrin (1), piperidine, and catalytic amounts of [La(OTf)3]. 3,5-Bis(5,10,15,20-tetraphenylporphyrin-2-ylmethyl)pyridine (2) was fully characterized and its sensing ability towards Zn(2+), Cu(2+), Hg(2+), Cd(2+), and Ag(+) was evaluated in solution by absorption and fluorescence spectroscopy and in gas phase by using matrix-assisted laser desorption/ionization (MALDI)-TOF mass spectrometry. Strong changes in the ground and excited state were detected in the case of the soft metal ions Zn(2+), Cd(2+), Hg(2+), and Cu(2+). A three-metal-per-ligand molar ratio was obtained in all cases and a significant ratiometric behavior was observed in the presence of Zn(2+) with the appearance of a new band at 608 nm, which can be assigned to a metal-to-ligand charge transfer. The system was able to quantify 79 ppb of Zn(2+) and the theoretical calculations are in accordance with the stoichiometry observed in solution. The gas-phase sensorial ability of compound 2 towards all metal ions was confirmed by using MALDI-TOF MS and in solid state by using polymeric films of polymethylmethacrylate (PMMA) doped with ligand 2. The results showed that compound 2 can be analytically used to develop new colorimetric molecular devices that are able to discriminate between Hg(2+) and Zn(2+) in solid phase. The crystal structure of Zn(II) complex of 3,5-bisporphyrinylpyridine was unequivocally elucidated by using single-crystal X-ray diffraction studies.

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

Cited by 83 publications

References 24 publications

Green and Red Fluorescent Dyes for Translational Applications in Imaging and Sensing Analytes: A Dual‐Color Flag

Green and Red Fluorescent Dyes for Translational Applications in Imaging and Sensing Analytes: A Dual‐Color Flag

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

A New 3,5‐Bisporphyrinylpyridine Derivative as a Fluorescent Ratiometric Probe for Zinc Ions

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