1982
DOI: 10.1021/ja00381a023
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Naphthonitrile-alkene exciplexes. Comparison of bimolecular and bichromophoric cases: effects of linking on fluorescence and photochemistry

Abstract: The fluorescence quenching and photochemistry of 2-methyl-, 4-methyl-, and 6-methyl-1-naphthonitrile with tetramethylethylene have been studied in nonpolar solvents. Stern-Volmer constants (benzene solvent) are 10.1, 15.7, and 7.2 M-', respectively, showing that quenching is insensitive to the position of the methyl group. Exciplex emission was observed in each case, and exciplex lifetimes were measured by single photon counting techniques. The methylnaphthonitriles react with tetramethylethylene to give 1-cya… Show more

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Cited by 55 publications
(26 citation statements)
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“…rich olefins to give cyclobutane and azetine products (1,8). The published investigations reveal important aspects of the mechanisms, in which the intermediacy of an exciplex has been implied (8-1 1).…”
Section: Introductionmentioning
confidence: 99%
“…rich olefins to give cyclobutane and azetine products (1,8). The published investigations reveal important aspects of the mechanisms, in which the intermediacy of an exciplex has been implied (8-1 1).…”
Section: Introductionmentioning
confidence: 99%
“…(7) Such studies again emphasize the important effect of solvent on the course and selectivity of the addition process. Adducts 17 and 18 are the sole products from 2,3-dimethylbut-2-ene with 1-and 2-naphthon- (45,46) It is also important to note that the cyclobutane compounds are photolabile and undergo decomposition unless Pyrex apparatus is employed. Use of Corex filtered radiation along with high reactant conversions yields 2-azobutadienes and azetines (cf.…”
Section: Ph_n:(mentioning
confidence: 99%
“…(67) Nevertheless the type of compound accessible by this one-step route would be difficult to obtain following even a multistep thermal pathway, and in particular cases, the photoprocess does display good selectivity or may be modified to do so. The potential complexity of the reaction mixture is typified by the products from the irradiation of benzene and buta-1,3-diene which comprise the meta 1,2-and cis-and trans-para-I,4-adducts 45,46, and 47, respectively, as well as the substitution product l-phenylbut-2-ene. (67) Under (46) the experimental conditions, the trans para 1,4-adduct 47 undergoes both thermal dimerization and further reaction with the diene to give 48 (49) respectively.…”
Section: Arenes and 13-dienesmentioning
confidence: 99%
“…[15] Why have the meta cycloadducts been overlooked so far? McCullough and co-workers [16] would have discovered them 25 years ago, if they had interpreted the facile cycloreversion of the ortho adducts correctly. However, the Mizuno group realised this fact and used it for the formation of the meta cycloadducts.…”
mentioning
confidence: 97%