Synthesis and Characterization of a New Fluorescent Zwitterionic Spirocyclic Meisenheimer Complex of 1,3,5-Trinitrobenzene

✍ Scribed by Rabih O. Al-Kaysi; Gonzalo Guirado; Edward J. Valente

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 112 KB
• Volume: 2004
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200400260

✦ Synopsis

Abstract

In this communication we present the first stable zwitterionic spirocyclic Meisenheimer compound based on an N→N rearrangement in the reaction between picric acid and diisopropylcarbodiimide. The structure was confirmed by single‐crystal X‐ray diffraction. Furthermore, this compound exhibits interesting fluorescence properties (φ~f~ = 0.4−0.5), not shared with a typical Meisenheimer complex, and a fluorescence lifetime (τ = 9.1 ns) in dichloromethane. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)