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Naphthalene diimides with improved solubility for visible light photoredox catalysis

Reiß, B.; Wagenknecht, H.-A.

Abstract (englisch):
Five core-substituted naphthalene diimides bearing two dialkylamino groups were synthesized as potential visible light photoredox catalysts and characterized by methods of optical spectroscopy and electrochemistry in comparison with one unsubstituted naphthalene diimide as reference. The core-substituted naphthalene diimides differ by the alkyl groups at the imide nitrogens and at the nitrogens of the two substituents at the core in order to enhance their solubility in DMF and thereby enhance their photoredox catalytic potential. The 1-ethylpropyl group as rather short and branched alkyl substituent at the imide nitrogen and the n-propyl group as short and unbranched one at the core amines yielded the best solubilities. The electron-donating diaminoalkyl substituents together with the electron-deficient aromatic core of the naphthalene diimides increase the charge-transfer character of their photoexcited states and thus shift their absorption into the visible light (500–650 nm). The excited state reduction potential was estimated to be approximately +1.0 V (vs SCE) which is sufficient to photocatalyze typical organic reactions. The photoredox catalytic activity in the visible light range was tested by the α-alkylation of 1-octanal as benchmark reaction. ... mehr

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Verlagsausgabe §
DOI: 10.5445/IR/1000098766
Veröffentlicht am 09.10.2019
Coverbild
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Jahr 2019
Sprache Englisch
Identifikator ISSN: 1860-5397, 2195-951X
KITopen-ID: 1000098766
Erschienen in Beilstein journal of organic chemistry
Band 15
Seiten 2043-2051
Vorab online veröffentlicht am 27.08.2019
Schlagworte chromophore; dyes; electrochemistry; photochemistry; photoredox catalysis
Nachgewiesen in Scopus
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