A 1,3‐Indandione‐Functionalized Tetraphenylethene: Aggregation‐Induced Emission,Solvatochromism, Mechanochromism,and Potential Application as a Multiresponsive Fluorescent Probe |
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| Authors: | Jiaqi Tong Yijia Wang Dr Ju Mei Dr Jian Wang Prof Anjun Qin Prof Jing Zhi Sun Prof Ben Zhong Tang |
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| Affiliation: | 1. MoE Key Laboratory of Macromolecule Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027 (China), Fax: (+86)?571‐87953734;2. Department of Chemistry, Institute for Advanced Study, State Key Laboratory of Molecular NeuroScience and Division of Biomedical Engineering, The Hong Kong University of Science &Technology, Clear Water Bay, Kowloon, Hong Kong (China), Fax: (+852)?23581594 |
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| Abstract: | A tetraphenylethene (TPE) derivative substituted with the electron‐acceptor 1,3‐indandione (IND) group was designed and prepared. The targeted IND‐TPE reserves the intrinsic aggregation‐induced emission (AIE) property of the TPE moiety. Meanwhile, owing to the decorated IND moiety, IND‐TPE demonstrates intramolecular charge‐transfer process and pronounced solvatochromic behavior. When the solvent is changed from apolar toluene to highly polar acetonitrile, the emission peak redshifts from 543 to 597 nm. IND‐TPE solid samples show an evident mechanochromic process. Grinding of the as‐prepared powder sample induces a redshift of emission from green (peak at 515 nm) to orange (peak at 570 nm). The mechanochromic process is reversible in multiple grinding–thermal annealing and grinding–solvent‐fuming cycles, and the emission of the solid sample switches between orange (ground) and yellow (thermal/solvent‐fuming‐treated) colors. The mechanochromism is ascribed to the phase transition between amorphous and crystalline states. IND‐TPE undergoes a hydrolysis reaction in basic aqueous solution, thus the red‐orange emission can be quenched by OH? or other species that can induce the generation of sufficient OH?. Accordingly, IND‐TPE has been used to discriminatively detect arginine and lysine from other amino acids, due to their basic nature. The experimental data are satisfactory. Moreover, the hydrolyzation product of IND‐TPE is weakly emissive in the resultant mixture but becomes highly blue‐emissive after the illumination for a period by UV light. Thus IND‐TPE can be used as a dual‐responsive fluorescent probe, which may extend the application of TPE‐based molecular probes in chemical and biological categories. |
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| Keywords: | fluorescence fluorescent probes mechanochromism solvatochromism UV/Vis spectroscopy |
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