Strongly fluorescent dipyrrinones. Internal quenching |
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Authors: | Stefan E Boiadjiev and David A Lightner |
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Institution: | (1) Department of Chemistry, University of Nevada, Reno, NV 89557-0020, USA; |
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Abstract: | Yellow N,N′-carbonyl-bridged dipyrrinones can generally be prepared from dipyrrinones simply by reaction with N,N′-carbonyldiimidazole in the presence of a strong, non-nucleophilic base. They are typically intensely fluorescent, with fluorescent
quantum yields approaching 1.0. In an effort to shift the excitation wavelength, and thus the fluorescence emissions, strongly
to the red, we prepared bridged dipyrrinones conjugated with thiobarbituric acid and Meldrum’s acid substituents at C-9. Such conjugation causes the dipyrrinones to have a magenta color (absorption wavelength shifted
from ∼400 nm of a typical dipyrrinone to ∼550 nm of the dipyrrinone conjugate). For comparison, we also prepared analogs with
formyl, carboxyl, acrylate, and acetyl substituents at C-9. Unexpectedly and uniquely, the 9-CHO substituent caused the fluorescence
quantum yield to drop to ∼10−3 while carboethoxy substituent exerted only a minor influence. |
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