Spiro-functionalized polyfluorenes을 위한 모노머와 Palladacycles을 위한 Oligoethylenedioxythiophenes의 합성연구
Synthetic Studies on Monomers for Spiro-Functionalized Polyfluorenes and Oligoethylenedioxythiophenes for Palladacycles
팔라듐 Palladacycles Oligoethylenedioxythiophenes 화학;
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In order to synthesize light emitting polymers some monomers were prepared. Thus, 9,9-Bis(1,1-dimethyloctylsilyl)-2,7-bis- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)fluorene (24a) and 9,9-bis(isopropyldimethylsilyl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)fluorene (24b) were synthesized from the reaction of 2,7-dibromo-9,9-bis(1,1-dimethyloctylsilyl)fluorene (23a) and 2,7-dibromo-9,9-bis(1,1-dimethylisopropylsilyl)fluorene (23b) with n-BuLi in THF followed by treating with pinacol borate in 31% and 36% yields, respectively. 2,7-dibromo-9,9'-spirobifluorene (26) was prepared by the treatment of 2-bromobiphenyl with Mg and I2 in ether followed by the reaction with 2,7-dibromofluorenone (25) in 75% yield. 2-(4-tert-butylphenyl)-5-[3,5-dibromo-4-(2-ethylhexyl- oxy)phenyl]-[1,3,4]-oxadiazole (32) was obtained by the cyclization of 4-tert-butylbenzoyl N'-[3,5-Dibromo-4- (2-ethylhexyloxy)benzoylhydrazide (31) in POCl_(3) in 85% yield. 2,5-bis(diphenylphosphanyl)-3,4-ethylenedioxythiophene (37), 5,5'-bis(diphenylphosphanyl)-2,2'-bi(3,4-ethylenedioxythiophene) (38) and 5,5"-Bis(diphenylphosphanyl)-3',4'-ethylenedioxy- 2,2':5',2"-terthiophene (39) were prepared by the treatment of the corresponding thienyl oligomers with n-BuLi in THF followed by quenching with chlorodiphenylphosphine in 64-77% yields. The synthesized monomers were characterized by spectroscopic methods.