Abstract
Strongly fluorescent dipyrrinones can be prepared by bridging the pyrrole and lactam nitrogens with a carbonyl group, from reaction with N,N′-carbonyldiimidazole in the presence of a strong, non-nucleophilic base. The yellow, N,N′-carbonyl-bridged dipyrrinones typically have fluorescent quantum yields (φF) approaching 1.0. Thus, in chloroform, N,N′-bridged 9H-dipyrrinones with β-alkyl substituents: 2,3-diethyl-7,8-dimethyl has φF = 0.90 (λem = 465 nm) and 2,3-dimethyl-7,8-dimethoxy has φF = 0.84 (λem = 482 nm). In contrast, 2,3-dimethoxy-7,8-dimethyl and 2,3,7,8-tetramethoxy show red-shifted λem but with strongly reduced φF: φF = 0.10 (λem = 511 nm) and 0.08 (λem = 511 nm), respectively. Methoxy substituents on the lactam, but not the pyrrole ring act to quench the fluorescence and shift the emission and excitation wavelengths bathochromically. The first X-ray crystal structure of an N,N′-carbonyl-bridged dipyrrinone was obtained from 7,8-dimethoxy-2,3-dimethyl-10H-dipyrrin-1-one.
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Correspondence: David A. Lightner, Department of Chemistry, University of Nevada, Reno, Nevada 89557-0020, USA.
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Dey, S., Lightner, D. Methoxyl-induced fluorescence quenching in N,N′-bridged 9H-dipyrrinones and an X-ray crystal structure. Monatsh Chem 139, 1377–1385 (2008). https://doi.org/10.1007/s00706-008-0924-2
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DOI: https://doi.org/10.1007/s00706-008-0924-2