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One‐Pot Functionalization of Graphene with Porphyrin through Cycloaddition Reactions
Author(s) -
Zhang Xiaoyan,
Hou Lili,
Cnossen Arjen,
Coleman Anthony C.,
Ivashenko Oleksii,
Rudolf Petra,
van Wees Bart J.,
Browne Wesley R.,
Feringa Ben L.
Publication year - 2011
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.201100980
Subject(s) - graphene , phosphorescence , porphyrin , photochemistry , raman spectroscopy , quenching (fluorescence) , thermogravimetric analysis , materials science , fourier transform infrared spectroscopy , tetraphenylporphyrin , covalent bond , fluorescence spectroscopy , spectroscopy , fluorescence , chemistry , organic chemistry , chemical engineering , nanotechnology , physics , engineering , quantum mechanics , optics
Two types of graphene‐based hybrid materials, graphene‐TPP (TPP=tetraphenylporphyrin) and graphene‐PdTPP (PdTPP=palladium tetraphenylporphyrin), were prepared directly from pristine graphene through one‐pot cycloaddition reactions. The hybrid materials were characterized by thermogravimetric analysis (TGA), by TEM, by UV/Vis, FTIR, Raman, and luminescence spectroscopy, and by fluorescence/phosphorescence lifetime measurements. The presence of the covalent linkages between graphene and porphyrin was confirmed by FTIR and Raman spectroscopy and further supported by control experiments. The presence of TPP (or PdTPP) in the hybrid material was demonstrated by UV/Vis spectroscopy, with TGA results indicating that the graphene‐TPP and graphene‐PdTPP hybrid materials contained approximately 18 % TPP and 20 % PdTPP. The quenching of fluorescence (or phosphorescence) and reduced lifetimes suggest excited state energy/electron transfer between graphene and the covalently attached TPP (or PdTPP) molecules.