Through-space interaction and its influence on the photoreactivity of 2,4-di-(1,2-naphthoquinone-2-diazide-5-sulphonyl-oxy)-benzophenone

Add time:07/26/2019    Source:sciencedirect.com

Different molecular environments were found for the two 1,2-naphthoquinone-2-diazide (NQD) substituents in 2,4-di-(1,2-naphthoquinone-2-diazide-5-sulphonyl-oxy)-benzophenone (2,4-NQD2-BP), detected by quantum chemical calculations of the molecular structure and by single-crystal X-ray analysis of the model compounds 4-(1,2-naphthoquinone-2-diazide-5-sulphonyl-oxy)-benzophenone (4-NQD-BP) and 2-(1,2-naphthoquinone-2-diazide-5-sulphonyl-oxy)-benzophenone (2-NQD-BP). The different electronic structures of the NQD substituents, detected using 1H, 13C and 15N nuclear magnetic resonance (NMR) and UV spectroscopy, are a result of different through-space interactions. The effect of the change in the electronic structure on the photoreactivity was determined using high performance liquid chromatography (HPLC). The quantum yields of photolysis of the NQD substituents are 0.17 and 0.30.

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