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Polarized Fluorescence of N-Salicylideneaniline Derivatives by Direct Exchange from Photoaligned N-Benzylideneaniline Side Groups in Liquid Crystalline Polymeric Films

Mizuki Tanaka ,1Hinano Yamaguchi ,1Mizuho Kondo ,1Moritsugu Sakamoto ,2,3Tomoyuki Sasaki ,2,3Hiroshi Ono ,2,3 and Nobuhiro Kawatsuki *1,3
1Department of Applied Chemistry, Graduate School of Engineering, University of Hyogo, 2188 Shosha, Himeji 671-2280
2Department of Electrical Engineering, Nagaoka University of Technology, 1603-1 Kamitomioka, Nagaoka 940-2188
3Japan Science and Technology Agency (JST), Core Research for Evolutional Science and Technology (CREST), Chiyoda-ku, Tokyo 102-0076, Japan
https://doi.org/10.1246/cl.230317

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Abstract

Photoalignment of liquid crystalline polymer with N-benzylideneaniline (NBA) side groups and subsequent in situ exchange achieves polarized fluorescence of oriented N-salicylideneaniline (SA) derivatives. In situ hydrolysis of NBA and condensation with 2-hydroxybenzaldehyde derivatives form oriented SA side groups. SA exhibits excited state intramolecular proton transfer (ESIPT), inducing polarized fluorescence with a 2.3 polarization ratio. The emissive wavelength depends on the 2-hydroxybenzaldehyde derivative. Stepwise formation of different oriented SA side groups allows for color tuning of the oriented film.

figure

Photoalignment of liquid crystalline polymer with N-benzylideneaniline (NBA) side groups and subsequent in situ exchange achieves polarized fluorescence of oriented N-salicylideneaniline (SA) derivatives with a 2.3 polarization ratio. In situ hydrolysis of NBA and condensation with 2-hydroxybenzaldehyde derivatives form oriented SA side groups. The emissive wavelength depends on the 2-hydroxybenzaldehyde derivative and color tuning of the oriented film is demonstrated.

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