2018
DOI: 10.1002/chem.201705620
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Customizing Photoredox Properties of PXX‐based Dyes through Energy Level Rigid Shifts of Frontier Molecular Orbitals

Abstract: Here we describe the synthesis of electron-rich PXX derivatives in which the energy levels of the excited states have been rigidly shifted through the insertion of imide groups. This has allowed the development of a new series of oxygen-doped photoredox-active chromophores with improved oxidizing and reducing properties. Capitalizing on the dehalogenation of organic halides as a model reaction, we could investigate the photooxidative and photoreductive potential of these molecules in model chemical transformat… Show more

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Cited by 35 publications
(74 citation statements)
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“…1 H NMR ((CD3)2SO, 300 MHz): δ 10.46 (s, 2H), 8.33 (s, 2H), 8.28 (dd, 2H, J = 7.1 Hz), 7.58 (dd, 2H, J = 7.9 Hz), 7.42 (dd, 2H, J = 8.4 Hz), 4.10 -4.06 (m, 4H), 1.69 -1.64 (m, 4H), 1.33 -1.26 (m, 20H), 0.86 (t, 6H, J = 6.6 Hz). HRMS (MALDI-TOF): m/z [M + H] + Calcd for C40H45N2O6 649.3278; Found 649.3251.Characterization in accordance with data reported in the literature 10.…”
supporting
confidence: 83%
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“…1 H NMR ((CD3)2SO, 300 MHz): δ 10.46 (s, 2H), 8.33 (s, 2H), 8.28 (dd, 2H, J = 7.1 Hz), 7.58 (dd, 2H, J = 7.9 Hz), 7.42 (dd, 2H, J = 8.4 Hz), 4.10 -4.06 (m, 4H), 1.69 -1.64 (m, 4H), 1.33 -1.26 (m, 20H), 0.86 (t, 6H, J = 6.6 Hz). HRMS (MALDI-TOF): m/z [M + H] + Calcd for C40H45N2O6 649.3278; Found 649.3251.Characterization in accordance with data reported in the literature 10.…”
supporting
confidence: 83%
“…As depicted in the diagram, the N-substituents display very similar HOMO and LUMO energy levels, whereas only 2 Per has a significantly lowered LUMO level (Figures 3, S58 and S59). (10). c HOMO and LUMO energies are calculated from the respective halfwave potential by assuming that the formal potential of the ferrocene redox couple, taken as a reference, is at -5.1 eV vs. vacuum and following the formulae: EHOMO = E 1/2 ox,1 -5.1 (eV) and ELUMO = E 1/2 red,1 -5.1 (eV).…”
Section: Absorptionmentioning
confidence: 99%
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“…Therefore, researchers continue to search for more suitable photosensitizers. 7,8) Peri-xanthenoxanthene (PXX) derivatives are polycyclic aromatic compounds with strong fluorescence and good optical properties. With good charge transfer properties, thermal stability, and chemical stability, these compounds are often used as compositions of pigments, charge transfer complexes, and organic semiconductors in electronic devices.…”
Section: Introductionmentioning
confidence: 99%