Synthesis and photochemistry of the novel compound 5-methyl-2-[(1-pyrenylmethylene)amino]-phenol

ORGN 762

Stephany Smith, Ralph Isovitsch, risovits@whittier.edu, and Amy Moskun, amoskun@whittier.edu. Department of Chemistry, Whittier College, 13406 Philadelphia Street, Whittier, CA 90608
Schiff bases are imines formed by a condensation reaction of an aldehyde and an amine. Metal complexes of Schiff bases are of particular interest as materials in light emitting diodes. 5-methyl-2-[(1-pyrenylmethylene)amino]-phenol absorbs and emits strongly in the blue and UV regions. Electronic absorption spectra in chloroform solution have a strong absorption band near 415 nm, with an extinction coefficient of 90,000 M-1cm-1. Dilute solutions in chloroform (approx. 4 micromolar) show a broad emission spectrum in the region 400-525 nm, with vibrational fine structure. The coordination chemistry of the compound with zinc and the photochemistry of the zinc complex will also be discussed.