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Naphthalene diimides with improved solubility for visible light photoredox catalysis
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2019-08-27 , DOI: 10.3762/bjoc.15.201
Barbara Reiß 1 , Hans-Achim Wagenknecht 1
Affiliation  

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. Irradiations were performed with LEDs in the visible light range between 520 nm and 640 nm. The irradiation by visible light together with the use of an organic dye instead of a transition metal complex as photoredox catalyst improve the sustainability and make photoredox catalysis “greener”.

中文翻译:

具有改善的溶解度的萘二酰亚胺用于可见光光氧化还原催化

合成了五种带有两个二烷基氨基的核取代萘二酰亚胺作为潜在的可见光光氧化还原催化剂,并通过光谱和电化学方法对其进行了表征,并与一种未取代的萘二酰亚胺作为参考进行比较。核取代的萘二酰亚胺的不同之处在于酰亚胺氮上的烷基和核上两个取代基的氮上的烷基不同,以增强它们在DMF中的溶解度,从而增强它们的光氧化还原催化潜力。1-乙基丙基作为酰亚胺氮上相当短且支化的烷基取代基,而正丙基作为核心胺处的短且非支化的烷基取代基产生了最好的溶解度。给电子二氨基烷基取代基与萘二酰亚胺的缺电子芳香核一起增加了其光激发态的电荷转移特性,从而将其吸收转移到可见光(500-650 nm)。激发态还原电位估计约为+1.0 V(相对于SCE),足以光催化典型的有机反应。以1-辛醛的α-烷基化反应为基准反应,测试了可见光范围内的光氧化还原催化活性。使用 LED 在 520 nm 至 640 nm 之间的可见光范围内进行照射。可见光照射并使用有机染料代替过渡金属络合物作为光氧化还原催化剂提高了可持续性并使光氧化还原催化“更绿色”。
更新日期:2019-08-27
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