A Red to Near-IR Fluorogen: Aggregation-Induced Emission, Large Stokes Shift, High Solid Efficiency and Application in Cell-Imaging.
A tetraphenylethene (TPE) derivative modified with the strong electron acceptor 2-dicyano-methylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (TCF) was obtained in high yield by a simple two-step reaction. The resultant TPE-TCF showed evident aggregation-induced emission (AIE) features and pronounced solvatochromic behavior. Changing the solvent from apolar cyclohexane to highly polar acetonitrile, the emission peak shifted from 560 to 680 nm (120 nm redshift). In an acetonitrile solution and in the solid powder, the Stokes shifts are as large as 230 and 190 nm, respectively. The solid film emits red to near-IR (red-NIR) fluorescence with an emission peak at 670 nm and a quantum efficiency of 24.8 %. Taking the advantages of red-NIR emission and high efficiency, nanoparticles (NPs) of TPE-TCF were fabricated by using tat-modified 1,2-distearoylsn-glycero-3-phosphor-ethanol-amine-N-[methoxy-(polyethyl-eneglycol)-2000] as the encapsulation matrix. The obtained NPs showed perfect membrane penetrability and high fluorescent imaging quality of cell cytoplasm. Upon co-incubation with 4,6-diamidino-2-phenylindole (DAPI) in the presence of tritons, the capsulated TPE-TCF nanoparticles could enter into the nucleus and displayed similar staining properties to those of DAPI.
MoE Key Laboratory of Macromolecule Synthesis, and Functionalization Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, 310027, China.
Yi Jia
YJ
Wang
MoE Key Laboratory of Macromolecule Synthesis, and Functionalization Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, 310027, China.
Yang
Y
Shi
MoE Key Laboratory of Macromolecule Synthesis, and Functionalization Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, 310027, China.
Zhaoyang
Z
Wang
State Key Laboratory of Modern Optical Instrumentation, Centre for Optical and Electromagnetic Research, Zhejiang Provincial Key Laboratory for Sensing Technologies, JORCEP (Sino-Swedish Joint Research Centre of Photonics), Zhejiang University, Hangzhou, 310058, China.
Zhenfeng
Z
Zhu
Institute of Environmental Health, Zhejiang University, Hangzhou, 310058, China.
Xinyuan
X
Zhao
Guangdong Innovative Research Team, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640, China.
Han
H
Nie
State Key Laboratory of Modern Optical Instrumentation, Centre for Optical and Electromagnetic Research, Zhejiang Provincial Key Laboratory for Sensing Technologies, JORCEP (Sino-Swedish Joint Research Centre of Photonics), Zhejiang University, Hangzhou, 310058, China.
Jun
J
Qian
Guangdong Innovative Research Team, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640, China.
Anjun
A
Qin
MoE Key Laboratory of Macromolecule Synthesis, and Functionalization Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, 310027, China. sunjz@zju.edu.cn.
Jing Zhi
JZ
Sun
MoE Key Laboratory of Macromolecule Synthesis, and Functionalization Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, 310027, China.|Guangdong Innovative Research Team, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640, China.|Department of Chemistry, Institute for Advanced Study, State Key Laboratory of Molecular NeuroScience, and Division of Biomedical Engineering Institution, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China.
Ben Zhong
BZ
Tang
D005453:Fluorescence; D005663:Furans / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D053758:Nanoparticles / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D012997:Solvents; D019265:Spectroscopy, Near-Infrared; D013267:Stilbenes / Q000737:chemistry*
D005663:Furans; D007211:Indoles; D009570:Nitriles; D012997:Solvents; D013267:Stilbenes; C000617116:tetraphenylethylene; C007293:DAPI
Stokes shift; aggregation-induced emission; cell-imaging; red-NIR fluorescence; solvatochromism