Journal
DYES AND PIGMENTS
Volume 133, Issue -, Pages 354-362Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2016.06.016
Keywords
Hexaphenyl-1,3-butatiene; Aggregation induced emission; Isomerization; Mechanochromic
Funding
- National Basic Research Program of China (973 Program) [2013CB834704]
- National Natural Scientific Foundation of China [21474009, 51328302]
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E/Z isomers of hexaphenyl-1,3-butadiene (HPB) derivative containing dialdehyde groups, 4,4'-((1E,3E)1,2,3,4-tetraphenylbuta-1,3-diene-1,4-diyl)dibenzaldehyde (EE-HPB-CHO), 4,4'((1Z,3E)-1,2,3,4-tetraphenylbuta-1,3-diene-1,4-diyl)-dibenzaldehyde (EZ-HPB-CHO) and 4,4'((1Z,3Z)-1,2,3,4-tetra-phenylbuta-1,3-diene-1,4-diyl)dibenzaldehyde (ZZ-HPB-CHO), were firstly synthesized in one-pot and readily separated by silica gel column chromatography. The E/Z isomers containing conjugated diene exhibited remarkable differences in the fields of aggregation-induced emission (AIE) or aggregation enhancement emission (AEE) behavior, thermostability, and mechanochromic performance. Among them, EE-HPB-CHO with dense molecular packing and strong intermolecular interaction was a better AlEgen while the EZ- and ZZ-isomers exhibited AEE behavior. Moreover, EE-HPB-CHO hardly displayed the mechanochromic performance. EZ-HPB-CHO irreversibly exhibited a blue-shift of 23 nm by grinding treatment, which could not be restored by fuming with organic solvents or heating. In contrast, owing to its twisting conformation and relative loose packing, ZZ-HPB-CHO reversibly displayed a red-shift of 20 nm during multiple repeating cycles of grinding and fuming treatments, showing superior. mechanochromic performance. (C) 2016 Elsevier Ltd. All rights reserved.
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