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Dr. Zhijia Wang Mikhail Ivanov Dr. Yuting Gao Laura Bussotti Prof. Paolo Foggi Huimin Zhang Prof. Nino Russo Prof. Bernhard Dick Prof. Jianzhang Zhao Prof. Mariangela Di Donato Dr. Gloria Mazzone Prof. Liang Luo Prof. Matvey Fedin 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(5):1091-1102
Spin–orbit charge-transfer intersystem crossing (SOCT-ISC) is useful for the preparation of heavy atom-free triplet photosensitisers (PSs). Herein, a series of perylene-Bodipy compact electron donor/acceptor dyads showing efficient SOCT-ISC is prepared. The photophysical properties of the dyads were studied with steady-state and time-resolved spectroscopies. Efficient triplet state formation (quantum yield ΦT=60 %) was observed, with a triplet state lifetime (τT=436 μs) much longer than that accessed with the conventional heavy atom effect (τT=62 μs). The SOCT-ISC mechanism was unambiguously confirmed by direct excitation of the charge transfer (CT) absorption band by using nanosecond transient absorption spectroscopy and time-resolved electron paramagnetic resonance (TREPR) spectroscopy. The factors affecting the SOCT-ISC efficiency include the geometry, the potential energy surface of the torsion, the spin density for the atoms of the linker, solvent polarity, and the energy matching of the 1CT/3LE states. Remarkably, these heavy atom-free triplet PSs were demonstrated as a new type of efficient photodynamic therapy (PDT) reagents (phototoxicity, EC50=75 nm ), with a negligible dark toxicity (EC50=78.1 μm ) compared with the conventional heavy atom PSs (dark toxicity, EC50=6.0 μm, light toxicity, EC50=4.0 nm ). This study provides in-depth understanding of the SOCT-ISC, unveils the design principles of triplet PSs based on SOCT-ISC, and underlines their application as a new generation of potent PDT reagents. 相似文献
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Infinite Polyiodide Chains in the Pyrroloperylene–Iodine Complex: Insights into the Starch–Iodine and Perylene–Iodine Complexes 下载免费PDF全文
Dr. Sheri Madhu Hayden A. Evans Dr. Vicky V. T. Doan‐Nguyen Dr. John G. Labram Dr. Guang Wu Prof. Dr. Michael L. Chabinyc Prof. Dr. Ram Seshadri Prof. Dr. Fred Wudl 《Angewandte Chemie (International ed. in English)》2016,55(28):8032-8035
We report the preparation and X‐ray crystallographic characterization of the first crystalline homoatomic polymer chain, which is part of a semiconducting pyrroloperylene–iodine complex. The crystal structure contains infinite polyiodide I∞δ?. Interestingly, the structure of iodine within the insoluble, blue starch–iodine complex has long remained elusive, but has been speculated as having infinite chains of iodine. Close similarities in the low‐wavenumber Raman spectra of the title compound and starch–iodine point to such infinite polyiodide chains in the latter as well. 相似文献
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Benjamin A. R. Günther Dr. Sebastian Höfener Dr. Ute Zschieschang Prof. Dr. Hubert Wadepohl Dr. Hagen Klauk Prof. Dr. Lutz H. Gade 《Chemistry (Weinheim an der Bergstrasse, Germany)》2019,25(64):14669-14678
A new synthesis of tetraazaperopyrenes (TAPPs) starting from a halogenated perylene derivative 3,4,9,10- tetrabromo-1,6,7,12-tetrachloroperylene ( 1 ) gave access to bay-substituted TAPPs for the first time. Selective lithiation of the bromine-positions and subsequent addition of tosyl azide led to the formation of the tetraazidotetrachloroperylene ( 2 ), which was subsequently reduced by addition of sodium borohydride to the corresponding tetraaminotetrachloroperylene ( 3 ). Oxidation to its semiquinoidal form 4 and subsequent cyclization with acid chlorides gave rise to a series of bay-chlorinated TAPPs. Whereas the aromatic core of the previously studied ortho-substituted TAPPs was found to be planar, the steric pressure of the two chlorine substituents on each side leads to the twist of the peropyrene core of approximately 30 degrees, a structural feature also observed in other bay-substituted perylene derivatives. An experimental and computational analysis reveals that introducing chloride substituents at these positions leads to slightly increased electron affinities (EA) enabling the selective generation and characterization of the reduced mono-anionic radicals and closed shell di-anionic species. These anions were isolated and characterized by UV/Vis spectroscopy and EPR or NMR, respectively. Processing of the bay-chlorinated TAPPs in n-channel organic TFTs revealed electron mobilities of 0.001 to 0.003 cm2 V−1 s−1. These reduced electron mobilities compared to the ortho-halogenated TAPPs are thought to be rooted in the less densely packed solid-state structures. 相似文献
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Dr. Yongjun Li Zhihong Qing Yanwen Yu Taifeng Liu Runsheng Jiang Prof. Yuliang Li 《化学:亚洲杂志》2012,7(8):1934-1939
The synthesis of 1,10‐dihydroxyperylene bisimides by nucleophilic substitution of brominated perylene bisimide is described. 1,10‐Dihydroxyperylene bisimides formed J aggregates in nonpolar solvents and showed a clearly redshifted absorption band. The solvent polarity also influenced the hydrogen bond with the hydroxyl group, and thus, the photophysical properties of perylene bisimide. The photophysical properties of these dihydroxyperylene perylene bisimides can also be tuned by changing charge transfer from the hydroxyl groups to the perylene core through the introduction of metal ions. 相似文献
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Back Cover: Versatile Colorant Syntheses by Multiple Condensations of Acetyl Anilines with Perylene Anhydrides (Angew. Chem. Int. Ed. 7/2015) 下载免费PDF全文
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Versatile Colorant Syntheses by Multiple Condensations of Acetyl Anilines with Perylene Anhydrides 下载免费PDF全文
Daniel Jänsch Dr. Chen Li Dr. Long Chen Dr. Manfred Wagner Prof. Dr. Klaus Müllen 《Angewandte Chemie (International ed. in English)》2015,54(7):2285-2289
We report a key step forward in rylene chemistry: the transformation of rylenes into novel chromophore families. The imidization of rylene anhydrides with 2‐acetyl anilines could be controlled by the choice of the solvent, thus causing a transformation into either a 4‐hydroxyquinoline (4‐HQ) or a 4‐oxoquinoline (4‐OQ) unit. The 4‐OQ motif contains an aminoenone group formed by intramolecular aldol condensation and is the first vinylogous rylene imide. The concept of vinylogy was further developed by utilizing 2,6‐diacetyl aniline leading to an 3a‐aza‐1,6‐phenalenedione‐extended rylene skeleton fully embracing the nitrogen atom. By functionalization of the aminoenone motifs, for example, malononitrile addition at the carbonyl groups, the optical and electronic properties could be further tuned. 相似文献