Excited state intramolecular proton transfer in 1-hydroxypyrene

M Lukeman, MD Burns, P Wan

Index: Lukeman, Matthew; Burns, Misty-Dawn; Wan, Peter Canadian Journal of Chemistry, 2011 , vol. 89, # 3 p. 433 - 440

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Citation Number: 14

Abstract

1-Hydroxypyrene (1) shows unusual acid-base chemistry in its singlet excited state. Whereas most hydroxyarenes experience a marked enhancement in their acidity when excited, and rapidly deprotonate to give the corresponding phenolate anion, this is not an important pathway for 1, despite theoretical predictions that 1 should experience enhanced acidity as well. In this work, we demonstrate that 1 undergoes a competing excited state ...