A Series of Imidazole Derivatives: Synthesis, Two-Photon Absorption, and Application for Bioimaging.

Yingzhong Zhu,Lufei Xiao,Meng Zhao,Hui Wang,Qiong Zhang,Shengli Li,Hongping Zhou,Jieying Wu,Yupeng Tian,Jiazheng Zhou

doi:10.1155/2015/965386

Abstract

A new series of D-π-A type imidazole derivatives have been synthesized and characterized. Two corresponding imidazolium salts (iodine and hexafluorophosphate) were prepared from the imidazole compound. Their electron-withdrawing ability can be largely tunable by salt formation reaction or ion exchange. UV-vis absorption and single-photon fluorescence spectra have been systematically investigated in different solvents. The two-photon cross sections (δ 2PA) of the imidazole derivatives are measured by two-photon excited fluorescence (2PEF) method. Compared with those of T-1 (107 GM) and T-3 (96 GM), T-2 (imidazolium iodine salt) has a large two-photon absorption (2PA) cross section value of 276 GM. Furthermore, the cytotoxicity and applications in bioimaging for the imidazole derivatives were carried out. The results showed that T-1 can be used as a lysosomal tracker with high stability and water solubility within pHs of 4–6, while T-2 and T-3 can be used as probes for cell cytoplasm.

Highlights

Fluorescence biomarker has become a powerful tool for the monitoring and investigating of cellular processes in live tissues, as well as in vivo clinical related researches
Based on the above considerations, at present work, in order to obtain the material with large 2PA cross section, imidazole, triphenylamine, and styryl group were used as link to construct the three D-π-A chromophores
to cm−1 in DMF (T-1) crystalizes with two independent molecules in asymmetric unit, and the crystal of T-1 belongs to monoclinic system with P21/n space group

Summary

A Series of Imidazole Derivatives

A new series of D-π-A type imidazole derivatives have been synthesized and characterized. Two corresponding imidazolium salts (iodine and hexafluorophosphate) were prepared from the imidazole compound. Their electron-withdrawing ability can be largely tunable by salt formation reaction or ion exchange. The two-photon cross sections (δ2PA) of the imidazole derivatives are measured by two-photon excited fluorescence (2PEF) method. Compared with those of T-1 (107 GM) and T-3 (96 GM), T-2 (imidazolium iodine salt) has a large two-photon absorption (2PA) cross section value of 276 GM. The cytotoxicity and applications in bioimaging for the imidazole derivatives were carried out. The results showed that T-1 can be used as a lysosomal tracker with high stability and water solubility within pHs of 4–6, while T-2 and T-3 can be used as probes for cell cytoplasm

Introduction

Experiment

Synthesis

Results and Discussion

Conclusion