Lophines are derivatives of 2,4,5-triphenylimidizole and are known for their unique optical properties. The following lophine derivatives were synthesized, purified, and characterized: 2-(4-nitrophenyl)-4,5-diphenylimidizole, 2-(4-morpholinophenyl)-4,5-diphenylimidizole and 2-(4-diphenylaminophenyl)-4,5-diphenylimidizole. The lophines were synthesized by the reaction of benzil, p-substituted benzaldehyde and ammonium acetate in glacial acetic acid. This work explores the effect of substitution of electron donating and electron withdrawing groups on the photophysics of the molecule. All of the lophines show strong absorptions in the UV range and emission in the UV or visible region. The nitro substituted lophine has red shifted absorption and emission spectra. The nitro lophine exhibits a large Stokes shift of ~200 nm in both methanol and DMF. The emission lifetimes of these compounds range from less than 1 ns to 5 ns.

Synthesis and photophysics of luminescent nitro, morpholino, and diphenylamino substituted lophines

245th National Meeting (2013)

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