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Syntheses and photophysical properties of some 4-arylpyridinium salts

✍ Scribed by Charles J. Kelley; (The Late) Kwabena Ansu; (The Late) Wiranto Budisusetyo; Alem Ghiorghis; Yuanxi Qin; Joel M. Kauffman

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
136 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A number of 4‐arylpyridines, many methoxy substituted, were prepared by an efficient two‐step method involving aryl Grignard addition to 1‐methyl‐4‐piperidone and direct aromatization of the resulting 4‐aryl‐4‐piperidinols. The pyridines were N‐alkylated to give sulfonate salts desired for their fluorescent properties. Study of selected compounds as laser dyes revealed several structures to be efficient dyes lasing in the 530‐550 nm range. Two new diazaquaterphenyls were prepared and were quaternized. These salts exhibited intense fluorescence in the 420‐450 nm range, but would not lase. A phenolic azaterphenyl suitably substituted for excited state intramolecular proton transfer (ESIPT) did not fluoresce at all.

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