Synthesis and photochemical properties of 1,3-di-9-anthryl-2-propanol, 1,3-di-9-anthrylacetone, and related propano-linked anthracenes

Journal Article · Fri Jun 23 00:00:00 EDT 1989 · Journal of Organic Chemistry; (USA)

DOI:https://doi.org/10.1021/jo00274a040· OSTI ID:7155837

Becker, H D; Amin, K A ^[1]

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1. Chalmers Univ. of Technology, Gothenburg (Sweden)

9-anthryllithium reacts with epichlorohydrin to give 1,3-di-9-anthryl-2-propanol via 3-(9-anthryl)-1-chloro-2-hydroxypropane and 3-(9-anthryl)-1,2-epoxypropane. Oxidation of dianthryl-2-propanol with Dess-Martin reagent gave 1,3-di-9-anthrylacetone. Various other 1,3-bichromophoric anthracenes were synthesized by way of C-methylation of dianthrylacetone, 1,3-di-9-anthryl-1-propanone, and 1,3-di-9-anthrylpropenone. 9-Anthrylacetone, formed as byproduct in the reaction of anthryllithium with epichlorohydrin, was prepared from 9-anthrylacetaldehyde by Grignard reaction with methylmagnesium iodide and subsequent oxidation. The excited-state properties of dianthryl-2-propanol, dianthrylacetone, 1,3-di-9-anthryl-2-methyl-1-propanone, 1,3-di-9-anthryl-2-methyl-2-propanol, diastereomeric 1,3-di-9-anthryl-1-butanols, 1,3-di-9-anthryl-2-butanone, 1,3-di-9-anthryl-1-butanone, and diastereomeric 1,3-di-9-anthryl-2-methyl-1-butanones have been evaluated by fluorescence quantum yields, and by quantum yields for the isomerization by intramolecular 4{pi} + 4{pi} cycloaddition. Dianthryl-2-propanol, 1,3-di-9-antrhyl-2-methyl-2-propanol, dianthrylacetone, diastereomeric 1,3-di-9-anthryl-1-butanols, and 1,3-di-9-anthryl-2-butanone isomerize in their excited singlet state with quantum yields of 0.046, 0.021, 0.25, 0.23, and 0.22, respectively. The photochemical isomerization of those 1,3-bichromophoric anthrancenes which are characterized by a 9-anthroyl chromophore involves the excited triplet state, and the cyclization quantum yield may be as high as 0.72.

• OSTI ID: 7155837
• Journal Information: Journal of Organic Chemistry; (USA), Journal Name: Journal of Organic Chemistry; (USA) Vol. 54:13; ISSN JOCEA; ISSN 0022-3263
• Country of Publication: United States
• Language: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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