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Selective side‐chain oxidation of peralkylated pyrrometheneBF 2 complexes

1994; Wiley; Volume: 5; Issue: 3 Linguagem: Inglês

10.1002/hc.520050309

1098-1071

Govindarao Sathyamoorthi, Lionel T. Wolford, Anthony M. Haag, Joseph H. Boyer,

Luminescence and Fluorescent Materials

Abstract Treatment with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) oxidized 2,6‐diethyl‐1,3,5,7,8‐pentamethylpyrromethene–BF 2 complex 1 , 13,14‐trimethyl‐2, 3, 4, 5,9,10,11,12‐octahydroindomethene–BF 2 complex 5 , and 1,3,5,7,8‐pentamethyl‐1,2,3,5,6,7‐hexahydropyromethene–BF 2 complex 8 to the weakly fluorescent 3‐formyl, 5‐oxo, and 8‐formyl derivatives 4 , 6 , and 9 , respectively. The dye 1 was oxidized by lead tetraacetate to 1,7,8‐trimethyl‐2,6‐diethyl‐3,5‐diacetoxymethylpyrromethene–BF 2 complex 12 [λ f (ethanol) 538 nm, Φ 0.62, λ las (ethanol) 555–570 nm]. Catalytic reduction (Pd/C) converted the aldehyde 4 to 2,6‐diethyl‐3‐hydroxymethyl‐1,5,7,8‐tetramethylpyrromethene–BF 2 complex 10 [λ f (ethanol) 537 nm, Φ 0.70, λ las (ethanol) 547–575 nm].