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A Highly Emissive Water‐Soluble Phosphorus Corrole
Author(s) -
Naitana Mario L.,
Nardis Sara,
Pomarico Giuseppe,
Raggio Michele,
Caroleo Fabrizio,
Cicero Daniel O.,
Lentini Sara,
Prodi Luca,
Genovese Damiano,
Mitta Saisameera,
Sgarlata Anna,
Fanfoni Massimo,
Persichetti Luca,
Paolesse Roberto
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604233
Subject(s) - corrole , quantum yield , chemistry , yield (engineering) , oxide , photochemistry , graphene , inorganic chemistry , organic chemistry , nanotechnology , materials science , fluorescence , physics , quantum mechanics , metallurgy
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. 31 P NMR spectroscopy in CD 3 OD indicates that the P sulfonate complex has been isolated in a hexacoordinated geometry with two different ligands (L1=‐OH, L2=‐OCH 3 ), 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.