Excited state interactions in calix[4]arene-perylene bisimide dye conjugates:: Global and target analysis of supramolecular building blocks

被引:73
作者
Hippius, Catharina
van Stokkum, Ivo H. M.
Zangrando, E.
Williams, Rene M.
Wuerthner, Frank
机构
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
[2] Univ Wurzburg, Rontgen Res Ctr Complex Mat Syst, D-97074 Wurzburg, Germany
[3] Univ Amsterdam, Mol Photon Grp, Hoff Inst Mol Sci, NL-1018 WS Amsterdam, Netherlands
[4] Vrije Univ Amsterdam, Dept Phys & Astron, NL-1081 HV Amsterdam, Netherlands
[5] Univ Trieste, Dipartimento Sci Chim, I-34127 Trieste, Italy
关键词
D O I
10.1021/jp0733825
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The photophysical properties of two supramolecular building blocks oc and oc2 consisting of a perylene bisimide chromophore substituted with either one or two calix[4]arene units in the N-imide position as well as those of the reference compound oref without calix[4]arene substituents were investigated. A complete picture of the processes taking place after photoexcitation in toluene, CH2Cl2, and benzonitrile was obtained by means of UV/vis absorption, steady state and time-resolved emission, and femtosecond transient absorption spectroscopy. It has been found that the fluorescence emission of compounds oe (Phi(fl) = 0.03 in CH2Cl2) and oc2 (Phi(fl) < 0.01 in CH2Cl2) is almost completely quenched compared with the highly emissive reference compound oref (Phi(fl) = 0.99 in CH2Cl2) because of fast electron-transfer processes from the calix[4]arene moieties to the perylene bisimide chromophore. This predominantly takes place with rate constants of k(cs) = 3 x 10(10) s(-1) (tau(cs) = 32 ps) for compound oc and kcs = 9 x 1010 s-1 (tau(cs) = 11 ps) for compound oc2 (in CH2Cl2) leading to a short-lived charge-separated state consisting of the reduced perylene bisimide unit and the oxidized calix[4]rene moiety.
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收藏
页码:13988 / 13996
页数:9
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