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RSC Advances · 2015 ·Vol. 5 ·期 16 ·12007-12014 · IF 3.84

Host–guest interaction between fluoro-substituted azobenzene derivative and cyclodextrins

Lingxing Zhang,Huan Zhang,Fei Gao,Huiying Peng,Yonghong Ruan,Yuanze Xu,Wengui Weng

An azobenzene derivative (F-azo-COOH) was synthesized and could be E/Z isomerized by visible light. The host–guest interaction between F-azo-COOH and cyclodextrins (CDs) in alkaline aqueous solution was studied by NMR spectroscopy for the first time. The results revealed that F-azo-COOH did not form a stable host–guest complex with α-CD. However, both trans- and cis-F-azo-COOH could form stable 1 : 1 complexes with β-CD. Most interestingly, cis-F-azo-COOH could fit the cavity of β-CD more tightly (3.0 ± 0.3 × 103 M−1) than its trans form (2.1 ± 0.2 × 103 M−1), which was completely opposite to the conventional azobenzene/β-CD system.

CAS / MDL: 7585-39-9

研究领域: 化学 · 材料科学

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DYES AND PIGMENTS · 2016 · IF 4.055

Effect of E/Z isomerization on the aggregation-induced emission features and mechanochromic performance of dialdehyde-substituted hexaphenyl-1,3-butadiene

Yahui Zhang,Huiling Mao,Lingwei Kong,Yong Tian,Zhonglin Tian,Xiangkai Zeng,Junge Zhi,Jianbing Shi,Bin Tong,Yuping Dong

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 AIEgen 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.

研究领域: 有机化学 · 材料科学

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Host–guest interaction between fluoro-substituted azobenzene derivative and cyclodextrins

Effect of E/Z isomerization on the aggregation-induced emission features and mechanochromic performance of dialdehyde-substituted hexaphenyl-1,3-butadiene