Preparation of Pentafluorinated Phenyl-Monohydro[60]fullerenes

Abstract

Pentafluorinated phenyl-monohydro[60]fullerenes [C 60 (Ar f ) 5 H] are synthesized in good yields via reaction of the corresponding fluorinated phenyl copper reagent, itself prepared in situ from the fluorinated phenyl Grignard reagent (Ar f MgBr) and copper(I) bromide-dimethyl sulfide complex, with [60]fullerene (C 60 ) in 1,2-dichlorobenzene under a nitrogen atmosphere.

Synthesis of n‐type [60]Fullerene Derivatives with Sterically Bulky tert‐Butyl Groups for Vacuum Deposition Processes

“…We synthesized compounds 1 – 2 via a penta‐addition reaction using an organocopper reagent in a glass reactor [14,18] . The organocopper reagent was prepared using ArMgBr and CuBr•SMe 2 below −30 °C, and then a solution of [60]fullerene in o ‐dichlorobenzene (ODCB) was continuously injected into the reaction mixture.…”

“…A sublimed grade of [60]fullerene was used for addition reactions and device fabrication. Designed compounds were synthesized using the previously reported method with minor modifications [14–15,18–19] . Synthetic manner and characterization results of compound 1 , 2 , 4 , 5 , 6 and 8 have described in the supporting information.…”

“…We synthesized compounds 1-2 via a penta-addition reaction using an organocopper reagent in a glass reactor. [14,18] The organocopper reagent was prepared using ArMgBr and CuBr * SMe 2 below À 30 °C, and then a solution of [60]fullerene in o-dichlorobenzene (ODCB) was continuously injected into the reaction mixture. The reactor temperature was slowly increased to 25 °C to obtain (hydro)pentaaryl[60]fullerenes 1 and 2 in yields of 83.4% and 33.4%, respectively (Scheme 1).…”

“…Designed compounds were synthesized using the previously reported method with minor modifications. [14][15][18][19] Synthetic manner and characterization results of compound 1, 2, 4, 5, 6 and 8 have described in the supporting information. 1 H NMR spectra were recorded using Bruker ASCEND 500 (500 MHz; Bruker Corporation, Billerica, MA, USA) and AVANCE DPX 300 (300 MHz) instruments.…”

Pentafluorophenyl Transfer Reaction: Preparation of Pentafluorophenyl [60]Fullerene Adducts through Opening of Fullerene Epoxide Moiety with Trispentafluorophenylborane

“…Compared with perfluoroalkyl fullerenes, perfluorophenyl fullerene adducts are rarely studied. Several partially fluorinated-phenyl cyclopentadienyl type fullerene adducts have been reported including the 3,4,5-trifluorophenyl adduct . The reported method failed to introduce ortho -fluorophenyl or pentafluorophenyl group on to the fullerene cage .…”