How (Not?) to Make Diaminoacenaphthylene for Use in Preparing Carbonyl-Substituted Photochromes

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Dr. Jason Gillmore

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The main goal of the Gillmore research group is to prepare derivatives of perimidinespirohexadienone (PSHD) photochromes to “gate” photoinduced charge transfer (PICT). Photochromes are molecules that can isomerize from their short wavelength form (SW) to their long wavelength form (LW) in the presence of ultraviolet light. PSHDs revert from LW to SW thermally. To act as photochromic photooxidants, effectively “gating” PICT, LW must be much more reducible than SW. Based on computationally predicted reduction potentials, carbonyl-substituted PSHDs are promising synthetic targets for achieving this goal. Previous experimental results show that it is not possible to add carbonyls to the photochrome bottom before coupling. Thus, it will be necessary to prepare an acenaphthylene-bottomed PSHD. This requires the synthesis of diaminoacenaphthylene. This seemingly simple molecule has proved very difficult to make. After ruling out the most straightforward syntheses and the use of protecting groups, we now detail our many failed synthetic attempts and some newly proposed synthetic routes we are currently investigating. This work was supported by the National Science Foundation under Career Grant CHE-0952768.

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