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Ring Size Effects on Multi‐Stimuli Responsive Luminescent Properties of Cyclic Amine Substituted β‐Diketones and Difluoroboron Complexes
Author(s) -
Wang Fang,
Song Daniel,
Dickie Diane A.,
Fraser Cassandra L.
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201801576
Subject(s) - photochemistry , luminescence , solvatochromism , bathochromic shift , fluorescence , piperidine , amine gas treating , chemistry , ring size , triethylamine , substituent , boron , materials science , ring (chemistry) , organic chemistry , molecule , physics , optoelectronics , quantum mechanics
Abstract Emissive β‐diketones (bdks) and difluoroboron complexes (BF 2 bdks) show multi‐stimuli responsive luminescence in both solution and the solid state. A series of bdk ligands and boron coordinated dyes were synthesized with different cyclic amine substituents in the 4‐position to explore ring size effects on various luminescent properties, including solvatochromism, viscochromism, aggregation‐induced emission (AIE), mechanochromic luminescence (ML) and halochromism. Red‐shifted absorption and emission were observed in CH 2 Cl 2 for both bdk ligands and boron dyes with increasing substituent ring size. The compounds displayed bathochromic emission in more polar solvents, and higher fluorescence intensity in more viscous media. The AIE compounds exhibited enhanced emission when aggregated. For solid‐state properties, a large emission wavelength shift was shown for the piperidine substituted bdk after melt quenching on weighing paper. Large blue‐shifted emissions were observed in all the boron dye spin cast films after trifluoroacetic acid vapor annealing, and the original emissions were partially recovered after triethylamine vapor treatment.