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Excited state proton transfer in 3-methyl-7-azaindole dimer. Symmetry control

Journal of Physical Chemistry A, ISSN: 1089-5639, Vol: 110, Issue: 29, Page: 9116-9122
2006
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The concerted double proton transfer undergone by the C dimer of 7-azaindole upon electronic excitation has also been reported to occur in 3-methyl-7-azaindole monocrystals and in dimers of this compound under free-jet conditions. However, the results obtained in this work for the 3-methyl-7-azaindole dimer formed in a 10 M solution of the compound in 2-methylbutane suggest that the dimer produces no fluorescent signal consistent with a double proton transfer in the liquid phase or in a matrix. In this paper, the spectroscopic behavior of the doubly hydrogen bonded dimer of 3-methyl-7-azaindole is shown to provide a prominent example of molecular symmetry control over the spectroscopy of a substance. This interpretation opens up a new, interesting research avenue for exploring the ability of molecular symmetry to switch between protontransfer mechanisms. It should be noted that symmetry changes in the 3-methyl-7-azaindole dimer are caused by an out-of-phase internal rotation of the two methyl groups © 2006 American Chemical Society.

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