TY - JOUR
T1 - Asymmetric tetraphenyl-substituted butadienes with aggregation-induced emission characteristic
T2 - Synthesis, properties and applications
AU - Zhao, Xin
AU - Zhang, Chen
AU - Wu, Xinghui
AU - Zhang, Kai
AU - Shi, Jianbing
AU - Cai, Zhengxu
AU - Tong, Bin
AU - Chao, Cong
AU - Dong, Yuping
N1 - Publisher Copyright:
© 2023 Elsevier Ltd
PY - 2023/7
Y1 - 2023/7
N2 - Six asymmetric tetraphenyl-1,3-butadiene derivatives were firstly designed and synthesized. Their photophysical properties showed the six derivatives having aggregation-induced emission (AIE) characteristics. The single crystal structure of indanedione-containing tetraphenyl-1,3-butadiene showed that the distorted structure and a variety of strong intermolecular interactions limited the intramolecular movement to enhance the fluorescence emission. Cyanoacetate-containing tetraphenyl-1,3-butadiene (TPB-NC) and dimethylbarbituric-containing tetraphenyl-1,3-butadiene (TPB-BC) exhibited typical mechanofluorochromic (MFC) properties. Powder X-ray diffraction and polarizing microscope experiments were carried out to reveal the mechanochemical mechanism, and the results showed that MFC was mainly attributed to a transition from crystalline state to amorphous state. In addition, TPB-NC could selectively respond to butyl cholinesterase (BuChE) and glycyrrhetinic acid (GA) in real-time. The low limit of detection for BuChE and GA were 1.61 μg/mL and 0.03 μg/mL according to IUPAC-based approach, respectively. The work has significant role in guiding the design of AIE molecules and enlarging their applications.
AB - Six asymmetric tetraphenyl-1,3-butadiene derivatives were firstly designed and synthesized. Their photophysical properties showed the six derivatives having aggregation-induced emission (AIE) characteristics. The single crystal structure of indanedione-containing tetraphenyl-1,3-butadiene showed that the distorted structure and a variety of strong intermolecular interactions limited the intramolecular movement to enhance the fluorescence emission. Cyanoacetate-containing tetraphenyl-1,3-butadiene (TPB-NC) and dimethylbarbituric-containing tetraphenyl-1,3-butadiene (TPB-BC) exhibited typical mechanofluorochromic (MFC) properties. Powder X-ray diffraction and polarizing microscope experiments were carried out to reveal the mechanochemical mechanism, and the results showed that MFC was mainly attributed to a transition from crystalline state to amorphous state. In addition, TPB-NC could selectively respond to butyl cholinesterase (BuChE) and glycyrrhetinic acid (GA) in real-time. The low limit of detection for BuChE and GA were 1.61 μg/mL and 0.03 μg/mL according to IUPAC-based approach, respectively. The work has significant role in guiding the design of AIE molecules and enlarging their applications.
KW - Aggregation-induced emission
KW - Asymmetric tetraphenyl-1,3-butadiene derivatives
KW - Butyl cholinesterase
KW - Glycyrrhetinic acid
KW - Mechanofluorochromic
UR - http://www.scopus.com/inward/record.url?scp=85150918142&partnerID=8YFLogxK
U2 - 10.1016/j.dyepig.2023.111252
DO - 10.1016/j.dyepig.2023.111252
M3 - Article
AN - SCOPUS:85150918142
SN - 0143-7208
VL - 215
JO - Dyes and Pigments
JF - Dyes and Pigments
M1 - 111252
ER -
