Polarized Fluorescence of N-Salicylideneaniline Derivatives Formed by In Situ Exchange from N-Benzylideneaniline Side Groups in Photoaligned Liquid Crystalline Copolymer Films.

Abstract

Polarized fluorescence of oriented N-salicylideneaniline (SA) derivatives is explored based on the thermally stimulated photoinduced molecular reorientation of liquid crystalline (LC) copolymethacrylate with N-benzylideneaniline derivative (NBA2) and benzoic acid (BA) side groups. The LC copolymer films show significant cooperative molecular reorientation of the NBA2 and BA side groups (D > 0.7). Subsequent thermal hydrolysis of the NBA2 side groups yields free phenylamine moieties. These moieties can form oriented SA derivatives via in situ condensation with 2-hydroxybenzaldehyde derivatives. The excited-state intermolecular proton transfer of the oriented SA molecules induces polarized fluorescence at 510-548 nm with a polarization ratio up to 6.2. Direct in situ exchange from the oriented NBA2 to SA derivatives achieves polarized fluorescence similar to that of the SA side groups.