The synthesis, spectroscopic, and optical properties of the water-soluble phosphorus complex of a 2-sulfonato-10-(4-sulfonatophenyl)-5,15-dimesitylcorrole have been investigated. The compound was prepared by adopting a novel strategy for the corrole sulfonation, leading to the regioselective isomer in an almost quantitative yield. The phosphorus coordination has a key role in determining the corrole substitution pattern, limiting the formation of poly-substituted species, which affected the reaction of the corrole free base. The resulting complex shows excellent optical properties in terms of emission quantum yield, also in polar protic solvents, including water. 31P NMR spectroscopy in CD3OD indicates that the P sulfonate complex has been isolated in a hexacoordinated geometry with two different ligands (L1=-OH, L2=-OCH3), and it is prone to axial ligand exchange with methanol, with no evidence of intermediate pentacoordinated species. The morphological characterization of thin layers of the P corrole deposited onto an Au(111) surface showed that the addition of an intermediate layer of reduced graphene oxide allows for a better control of corrole aggregation, inducing also transformation of the Au(111) reconstructed surface. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

NAITANA, M.L., NARDIS, S., POMARICO, G., RAGGIO, M., CAROLEO, F., CICERO, D.O., et al. (2017). A Highly Emissive Water-Soluble Phosphorus Corrole. CHEMISTRY-A EUROPEAN JOURNAL, 23(4), 905-916 [10.1002/chem.201604233].

A Highly Emissive Water-Soluble Phosphorus Corrole

NAITANA, MARIO LUIGI;NARDIS, SARA;POMARICO, GIUSEPPE;RAGGIO, MICHELE;CAROLEO, FABRIZIO;CICERO, DANIEL OSCAR;LENTINI, SARA;MITTA, SAISAMEERA;SGARLATA, ANNA;FANFONI, MASSIMO;Persichetti, L;PAOLESSE, ROBERTO
2017

Abstract

The synthesis, spectroscopic, and optical properties of the water-soluble phosphorus complex of a 2-sulfonato-10-(4-sulfonatophenyl)-5,15-dimesitylcorrole have been investigated. The compound was prepared by adopting a novel strategy for the corrole sulfonation, leading to the regioselective isomer in an almost quantitative yield. The phosphorus coordination has a key role in determining the corrole substitution pattern, limiting the formation of poly-substituted species, which affected the reaction of the corrole free base. The resulting complex shows excellent optical properties in terms of emission quantum yield, also in polar protic solvents, including water. 31P NMR spectroscopy in CD3OD indicates that the P sulfonate complex has been isolated in a hexacoordinated geometry with two different ligands (L1=-OH, L2=-OCH3), and it is prone to axial ligand exchange with methanol, with no evidence of intermediate pentacoordinated species. The morphological characterization of thin layers of the P corrole deposited onto an Au(111) surface showed that the addition of an intermediate layer of reduced graphene oxide allows for a better control of corrole aggregation, inducing also transformation of the Au(111) reconstructed surface. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Pubblicato
Rilevanza internazionale
Articolo
Esperti anonimi
Settore CHIM/07 - Fondamenti Chimici delle Tecnologie
English
Con Impact Factor ISI
Coordination reactions; Gold; Gold deposits; Graphene; Ligands; Optical emission spectroscopy; Optical properties; Organic solvents; Phosphorus; Scanning probe microscopy; Sulfonation, Corroles; Emission quantum yield; Morphological characterization; Porphyrinoids; Reconstructed surfaces; Reduced graphene oxides; Substitution patterns; Water-soluble phosphorus, Polypyrroles; corrole; phosphorus; porphyrinoids; scanning probe microscopy; sulfonation
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85006340324&doi=10.1002/chem.201604233&partnerID=40&md5=1353d920bb0e5b6ba68095d3970ede8c
NAITANA, M.L., NARDIS, S., POMARICO, G., RAGGIO, M., CAROLEO, F., CICERO, D.O., et al. (2017). A Highly Emissive Water-Soluble Phosphorus Corrole. CHEMISTRY-A EUROPEAN JOURNAL, 23(4), 905-916 [10.1002/chem.201604233].
Naitana, Ml; Nardis, S; Pomarico, G; Raggio, M; Caroleo, F; Cicero, Do; Lentini, S; Prodi, L; Genovese, D; Mitta, S; Sgarlata, A; Fanfoni, M; Persichetti, L; Paolesse, R
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2108/175383
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