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Molecular Association of Singlet Excited State Methyl 2-Naphthoate; Effects of Excimer Formation On Photocycloaddition

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We have established that singlet excited methyl 2-naphthoate (*2MN) forms an emissive excimer reversibly in CH3CN at concentrations above 10-2 M. The rate constant for the excimer formation was indirectly determined from extended kinetic analysis of fluorescence intensity quenching to be ked = (2.9 ± 0.7) x 1010 M-1S-1 in CH3CN at 298 K; i.e., it appears to be diffusion controlled. The dissociation rate constant was found to be k-ed = (6.0 ± 1.5) x 109 s-1 that was an order of magnitude larger than the sum of either the excimer decay rate constants {(2.7 ± 0,5) x 108 s-1} or that of *2MN {(1.30 ± 0.05) x 108 s-1}. This method is shown to be useful for a totally reversible excimer (exciplex) fonnation with no new emission. The enthalpy and entropy of excimer association were determined from a Stevens-Ban plot to be -6.8 ± 0.1 kcal mol-1 and -19.6 ± 0.4 cal K-1 mol-1, respectively, where the latter signifies a rigid and ordered excimer structure. Both the *2MN monomer and excimer interacted with H2SO4 at the rate constants of (2.3 ± 0.1) x 109 M-1s-1 and (6.5 ± 1.7) x 109 M-1s-1, respectively. In contrast to the *2MN reaction, the excimer failed to react with acetylacetone as shown by no change in the excimer fluorescence relative to *2MN fluorescence and the subsequent kinetic analysis. The interaction of the *2MN excimer with H2SO4 does not lead to the emission of 2MNH+ and is also shown, by simulated calculation, not to contribute to a catalytic pathway of the 2+2 photocyloaddition between 2MN and acetylacetone.

Affiliations: 1: Department of Chemistry, Simon Fraser University, Burnaby, Canada V5A 1S6


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