Monatshefte für Chemie/Chemical Monthly

Synthesis, structure, and fluorescence of isomeric indolizinediones. Carbonyl-bridged isodipyrrinones

SE Boiadjiev, DA Lightner

Index: Boiadjiev, Stefan E.; Lightner, David A. Monatshefte fur Chemie, 2005 , vol. 136, # 4 p. 553 - 565

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Citation Number: 4

Abstract

Summary. In “one-pot” reactions, pyrrole-α-and β-aldehydes condense readily with 4-ethyl-3- methyl-3-pyrrolin-2-one to give isodipyrrinone analogs, which undergo intramolecular cyclization when the pyrrolealdehyde possesses an α or β-CO 2 R group. The resulting regioisomeric pyrroloindolizinediones, with structures confirmed by NMR analysis, exhibit strong fluorescence, with quantum yields (φ F) as high as 0.91 at λ em∼ 450–550 nm.