TY - JOUR
T1 - Regioselective Ru-catalyzed direct 2,5,8,11-alkylation of perylene bisimides
AU - Nakazono, Satomi
AU - Imazaki, Yusuke
AU - Yoo, Hyejin
AU - Yang, Jaesung
AU - Sasamori, Takahiro
AU - Tokitoh, Norihiro
AU - Cédric, Tassel
AU - Kageyama, Hiroshi
AU - Kim, Dongho
AU - Shinokubo, Hiroshi
AU - Osuka, Atsuhiro
PY - 2009/8/3
Y1 - 2009/8/3
N2 - A study was conducted to demonstrate the first selective synthesis of 2,5,8,11-substituted perlylene tetracarboxylic acid bisimides (PBI). A mixture of bis(N-ethylpropyl)PBI and trimethylvinylsilane was heated in mesitylene at 165°C for 60 hours in the presence of of 6 mol% of [RuH2(CO) (PPh3)3]. Tetraalkylated PBI was obtained in 94% yield after silica-gel separation. It was found that the alkylation of N-(2,6-diisopropyl)phenylPBI needed longer reaction times due to its lower solubility, but afforded the desired product in quantitative yield. It was observed that solubility in organic solvents was significantly enhanced after tetraalkylation. It was also found that the alkylation was unable to change the absorption and emission properties in the solution state significantly, but lowered molar extinction coefficients of the lowest energy absorption band.
AB - A study was conducted to demonstrate the first selective synthesis of 2,5,8,11-substituted perlylene tetracarboxylic acid bisimides (PBI). A mixture of bis(N-ethylpropyl)PBI and trimethylvinylsilane was heated in mesitylene at 165°C for 60 hours in the presence of of 6 mol% of [RuH2(CO) (PPh3)3]. Tetraalkylated PBI was obtained in 94% yield after silica-gel separation. It was found that the alkylation of N-(2,6-diisopropyl)phenylPBI needed longer reaction times due to its lower solubility, but afforded the desired product in quantitative yield. It was observed that solubility in organic solvents was significantly enhanced after tetraalkylation. It was also found that the alkylation was unable to change the absorption and emission properties in the solution state significantly, but lowered molar extinction coefficients of the lowest energy absorption band.
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U2 - 10.1002/chem.200901318
DO - 10.1002/chem.200901318
M3 - Article
C2 - 19575351
AN - SCOPUS:67949092673
SN - 0947-6539
VL - 15
SP - 7530
EP - 7533
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 31
ER -