Synthesis， Photophysical Properties， Theoretical Calculation and Cell Imaging of a Tetraphenylethene Imidazole Compound with Methoxy Group

doi:10.19894/j.issn.1000-0518.230019

Chinese Journal of Applied Chemistry ›› 2023, Vol. 40 ›› Issue (9): 1322-1329.DOI: 10.19894/j.issn.1000-0518.230019

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Synthesis， Photophysical Properties， Theoretical Calculation and Cell Imaging of a Tetraphenylethene Imidazole Compound with Methoxy Group

Da-Wei TONG¹, Ming KONG¹(), Yu-Bin XIANG²

^1.Nanjing Institute of Product Quality Inspection，Nanjing 210019，China
^2.School of Chemistry and Materials Science，Nanjing University of Information Science & Technology，Nanjing 210044，China

Received:2023-02-09 Accepted:2023-05-24 Published:2023-09-01 Online:2023-09-14
Contact: Ming KONG
About author:mingkong@smail.nju.edu.cn
Supported by:
the Key Science and Technology Program of Nanjing Administration for Market Regulation(Kj2021021);the Shuangchuang Program of Jiangsu Province(JSSCBS20221736);the National Natural Science Foundation of China(22205114);the Natural Science Foundation of Jiangsu Province(BK20190776)

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Abstract

Abstract:

A titled tetraphenylethene imidazole compound with methoxy group named 4，5-bis（4-methoxyphenyl）-2-（4-（1，2，2-triphenylvinyl）phenyl）-1H-imidazole（BTI） is synthesized by one step. The target BTI is fully characterized by NMR spectroscopy， mass spectrometry and elemental analysis. The single crystal structure of BTI is obtained by evaporation of the mother solutions. The photophysical properties of BTI are studied by UV-Vis absorption and fluorescence emission spectrum. By means of theoretical calculation， the excited state properties of BTI are elaborated. Finally， the application of BTI in cell imaging is studied. The results show that BTI exhibits typical aggregation-induced emission （AIE） properties with intramolecular charge transfer （ICT） character， and the experimental spectral data agree well with the theoretical calculation results. The cell imaging study shows that BTI can well penetrate the HepG2 cell membrane and perform one-and two-photon excitated confocal fluorescence imaging.

Key words: Aggregation-induced emission, Crystal structure, Theoretical calculation, Two-photon, Cell imaging

CLC Number:

O621.2

Da-Wei TONG, Ming KONG, Yu-Bin XIANG. Synthesis， Photophysical Properties， Theoretical Calculation and Cell Imaging of a Tetraphenylethene Imidazole Compound with Methoxy Group[J]. Chinese Journal of Applied Chemistry, 2023, 40(9): 1322-1329.

Figures/Tables 8

Fig.1 Synthetic route of BTI

Fig.2 The crystal structure of BTI （Thermal ellipsoids shown at the 30% probability level and the hydrogen atoms has been omitted for clarity）；（B） The hydrogen bonding interactions between adjacent molecules

Fig.3 The TG （A） and DSC （B） curve of BTI

Fig.4 The absorption （A） and emission （B） spectra of BTI in different solvents （concentration： 1×10-5 mol/L， slit width： 5 nm）

Fig.5 The fluorescence emission spectra of BTI in different volume fraction of ethanol and water mixed solution （A） and the variation of fluorescence intensity according to the water volume fraction （B）（concentration： 1×10-5 mol/L， slit width： 5 nm）

Table 1 The major electronic energy level of electron transitions and attributions for compound by TD-DFT calculations

Compound	OI ^a	ΔE/eV ^b	Cal.λ_max/nm ^c	Obs.λ_max/nm ^d	f ^e	Character
BTI	HOMO→LUMO	4.176 9	335	344	0.5457	ICT/π→π^*
BTI	HOMO→LUMO+1	4.639 8	302	299	0.1578	π→π^*

Fig.6 The optimize molecular structure and selected frontier molecular orbitals of BTI（A）， the calculated UV-Vis spectra from TD-DFT calculation（B）

Fig.7 The cytotoxic diagram in HepG2 cells of BTI （A） and the one- and two-photon confocal fluorescence images of BTI in HepG2 cells at different time （B）（incubated with the concentrations 10 μmol/L， two-photon excited wavelength at 700 nm， confocal fluorescence images were received by collecting the emissions at 450~600 nm）

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Synthesis， Photophysical Properties， Theoretical Calculation and Cell Imaging of a Tetraphenylethene Imidazole Compound with Methoxy Group

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