The Quenching Action of Benzoic Acid and Methyl Benzoate on the Fluorescence of Naphthalene Derivatives

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Abstract
1) The quenching action of benzoic acid (dimer) (BA) and methyl benzoate (MB) on the fluorescence of 2-naphthol (I), 2-naphthylamine (II), 2-naphthyl methyl ether (III) and N,N-dimethyl-2-naphthylamine (IV) in benzene and in cyclohexane has been studied. 2) MB has little or no quenching effect on the fluorescence of III and IV, whereas it shows a significant quenching action on I and II. The latter is due to the intermolecular hydrogen bonding between the fluorescer and the quencher (the H.B. mechanism). 3) BA shows quite a large quenching action on III and IV. All the results can be interpreted on the basis of a charge transfer mechanism for quenching (the C.T. mechanism). 4) The quenching action of BA is larger on I than on III, and larger on II than on IV, except for benzene solutions of II and IV, in which case the magnitudes are equal within the range of experimental error. These results has been discussed on the basis of a simultaneous occurrence of the C.T. and H.B. mechanisms.

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