4 years ago

Photochemistry of 1- and 2-Naphthols and Their Water Clusters: The Role of 1ππ*(La) Mediated Hydrogen Transfer to Carbon Atoms

Photochemistry of 1- and 2-Naphthols and Their Water Clusters: The Role of 1ππ*(La) Mediated Hydrogen Transfer to Carbon Atoms
Nađa Došlić, Nikola Basarić, Jurica Novak, Clémence Corminboeuf, Antonio Prlj
The computational analysis of the isomer- and conformer-dependent photochemistry of 1- and 2-naphthols and their microsolvated water clusters is motivated by their very different excited state reactivities. We present evidence that 1- and 2-naphthol follow distinct excited state deactivation pathways. The deactivation of 2-naphthols, 2-naphthol water clusters, as well as of the anti conformer of 1-naphthol is mediated by the optically dark 1πσ* state. The dynamics of the 1πσ* surface leads to the homolytic cleavage of the OH bond. On the contrary, the excited state deactivation of syn 1-naphthol and 1-naphthol water clusters follows an uncommon reaction pathway. Upon excitation to the bright 1ππ*(La) state, a highly specific excited state hydrogen transfer (ESHT) to carbon atoms C8 and C5 takes place, yielding 1,8- and 1,5-naphthoquinone methides. The ESHT pathway arises from the intrinsic electronic properties of the 1ππ*(La) state of 1-naphthols. Path to deactivation: Ab initio static and surface hopping dynamics computations show that 1- and 2-naphthol and their water clusters follow distinct excited state deactivation pathways (see scheme).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201700691

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