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Graphene Functionalisation with a Conjugated Poly(fluorene) by Click Coupling: Striking Electronic Properties in Solution
Author(s) -
Castelaín Marta,
Martínez Gerardo,
Merino Pablo,
MartínGago José Á.,
Segura José L.,
Ellis Gary,
Salavagione Horacio J.
Publication year - 2012
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.201102008
Subject(s) - fluorene , conjugated system , click chemistry , azide , graphene , alkyne , polymer chemistry , cycloaddition , raman spectroscopy , materials science , photochemistry , polymer , covalent bond , fourier transform infrared spectroscopy , chemistry , combinatorial chemistry , organic chemistry , chemical engineering , nanotechnology , catalysis , physics , engineering , optics
Graphene flakes covalently modified with a conjugated polymer, poly[(9,9‐dihexylfluorene)‐co‐alt‐(9,9‐bis‐(6‐azidohexyl)fluorene)] (PFA), were efficiently synthesised by a Cu‐catalysed Huisgen 1,3‐dipolar cycloaddition between alkyne‐modified graphene and an azide‐functionalised polymer. Two approaches for the modification of graphene with alkyne groups were investigated (coupling with a diazonium salt generated in situ or an amidation reaction) and the optimum conditions determined. The success of the click‐coupling approach was confirmed by FTIR, 1 H NMR, Raman, and X‐ray photoelectron spectroscopy (XPS). The absorption and emission spectra of the click product show a strong solvent dependency.