- Visible-Light-Promoted Efficient Aerobic Dehydrogenation of N-Heterocycles by a Tiny Organic Semiconductor Under Ambient Conditions
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An efficient reusable catalytic system has been developed based on perylene diimide (PDI) organic semiconductor for the aerobic dehydrogenation of N-heterocycles with visible light. This practical catalytic system without any additives proceeds under ambient conditions. The minute aggregates of PDI molecules on the surface of SiO2 nanospheres form tiny organic semiconductors, resulting in high-efficiency photo-oxidative activity. Notably, the robustness of this method is demonstrated by the synthesis of a wide range of N-heteroarenes, gram-scale experiments as well as reusability tests.
- Su, Chenliang,Yu, Kunyi,Zhang, Hanjie,Zhu, Yongfa
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supporting information
p. 1956 - 1960
(2020/04/10)
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- Electrochemistry, spectroscopy and electrogenerated chemiluminescence of perylene, terrylene, and quaterrylene diimides in aprotic solution
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The electrochemistry, UV-vis spectrophotometry, photoluminescence, and electrogenerated chemiluminescence (ECL) of perylenedicarboxylic imide, perylenetetracarboxylic diimide (PDI), terrylenetetracarboxylic diimide (TDI), and quaterrylenecarboxylic diimide (QDI) were investigated. All compounds undergo two reversible one-electron reductions and one reversible one-electron oxidation reaction. The first reduction potential shifts to less negative values and the potential for oxidation to less positive values for the diimide series with increasing size of the aromatic core. These changes in potential correlate well with orbital energies from molecular orbital calculations. The difference in potential between the first and Second reduction waves decreased with increasing distance between the imide groups, so that TDI and QDI show only a single reduction wave, equivalent to a two- electron reduction. These reduction potentials provide estimates for the equilibrium constant for disproportionation of the radical anion. Very stable ECL spectra of PDI or TDI generated by sequential production of the radical cation and radical anion at an electrode were observed; these were identical to the photoluminescence spectra A consideration of the energetics of the electron transfer reaction and the singlet energy leads to the conclusion that emission occurs mainly via generation of triplets followed by triplet- triplet annihilation (the T-route).
- Lee, Sang Kwon,Zu, Yanbing,Herrmann, Andreas,Geerts, Yves,Müllen, Kl?us,Bard, Allen J.
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p. 3513 - 3520
(2007/10/03)
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- Soluble Perylene Fluorescent Dyes with High Photostability
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The preparation of several 3,4,9,10-perylenebis(dicarboximides) 1 is described and their photostability quantitatively determined and discussed.It is shown, that substitution of the insoluble perylene dye pigments with tert-butyl groups causes solubility in organic solvents leading to high quantum yields of these dyes.
- Rademacher, Andreas,Maerkle, Suse,Langhals, Heinz
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p. 2927 - 2934
(2007/10/02)
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