2023
DOI: 10.26434/chemrxiv-2023-wps77
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Remote Electrostatic Repulsion Trigged by Excited State Antiaromaticity Relief as Origin of Photoacidity in an Organic Dye

Abstract: Photoacids are molecules which become (more) acidic under photoirradiation, and they find valuable applications in organic synthesis and biological chemistry. We herein report a new photoacid, HDMAPAN-(BF4)2, which functions by a different photoacidity mechanism than existing ones. HDMAPAN-(BF4)2, consisting of one dibenzotropylium and one anilinium moiety connected together by a biaryl C-C bond, shows an exceptionally low computed Delta_pKa(hv) (-12.3), which is within the range of superphotoacids. Surprising… Show more

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