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The Molecular Mechanism of Photochromism in Photo-Enolizable Quinoline and Napthyridine Derivatives
journal contribution
posted on 2012-12-20, 00:00 authored by S. Knippenberg, M. Schneider, P. Mangal, A. DreuwPhotochromism, the change of color upon irradiation,
is a general
property of quinoline derivatives, yet subtle differences in the geometric
structure influence its occurrence. To investigate this relation,
the mechanism of photoenolization of the photochromic compounds 3-benzoyl-2-benzyl-1-methyl-1H-quinoline-4-one (1) and 3-benzoyl-1,2-dibenzyl-1H-1,8 naphtyridin-4-one (2) as well as of the
structurally closely related but nonphotochromic 3-benzoyl-1-benzyl-2-methyl-1H-1,8-naphtyridin-4-one (3) has been investigated
theoretically using state-of-the-art quantum chemical methods. Focusing
on the difference between 2 and 3 and stressing
the absence of a phenyl group in the latter, the excited state potential
energy surfaces along the photoenolization coordinate have been calculated
for both. While the initial proton transfer initializing photoenolization
is feasible when the phenyl group is present in 1 and 2, it is suppressed in 3.