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Dinitriles Bearing AIE‐Active Moieties: Synthesis, E / Z Isomerization, and Fluorescence Properties
Author(s) -
Tasso Thiago Teixeira,
Furuyama Taniyuki,
Kobayashi Nagao
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406128
Subject(s) - tetraphenylethylene , thermochromism , isomerization , fluorescence , photochemistry , chemistry , aggregation induced emission , bearing (navigation) , polymer chemistry , organic chemistry , catalysis , physics , cartography , quantum mechanics , geography
Dinitriles bearing aggregation‐induced emission (AIE)‐active moieties [tetraphenylethylene (TPE) or diphenylphenanthrene (DPP)] were prepared. Compounds 4 (TPE‐linked) and 8 (DPP‐linked) showed considerably redshifted emission resulting from their large Stokes shifts and also strong fluorescence in the aggregated and solid states. Pure E and Z stereoisomers of both dinitriles were easily separated, and their isomerization equilibria and fluorescence properties were investigated. In addition to their pronounced AIEE behavior, 4 and 8 also showed various reversible chromic responses to external stimuli, namely, solvato‐, piezo‐, vapo‐, and thermochromism, which make them potential candidates for smart materials.