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

AlKaysi Rabih O. | Zendy; Guirado Gonzalo | Zendy; Valente Edward J. | Zendy

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

Author(s) -

AlKaysi Rabih O.,

Guirado Gonzalo,

Valente Edward J.

Publication year - 2004

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200400260

Subject(s) - chemistry , dichloromethane , picric acid , fluorescence , characterization (materials science) , crystal structure , stereochemistry , photochemistry , crystallography , organic chemistry , nanotechnology , solvent , physics , materials science , quantum mechanics

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)

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