Facile synthesis and separation of / isomers of aromatic-substituted tetraphenylethylene for investigating their fluorescent properties single crystal analysis

• Published in: Journal of materials chemistry. C, Materials for optical and electronic devices Materials for optical and electronic devices, 2019-04, Vol.7 (14), p.4155-4163
• Main Authors: Lu, Zhixiang, Yang, Shaoxiong, Liu, Xiaolan, Qin, Yu, Lu, Shuhan, Liu, Yanxiong, Zhao, Ruidun, Zheng, Liyan, Zhang, Hongbin
• Format: Article
• ISSN: 2050-7526; 2050-7534
• DOI: 10.1039/c9tc00446g

The intermolecular interactions and molecular packing form of fluorescent molecules have a huge impact on their optical properties, especially for AIE molecules. As a class of typical AIE molecules, tetraphenylethene (TPE) and its derivatives have prominent optical properties; nevertheless, separation of mixtures of E / Z isomers is a great challenge. Herein, a series of aromatic-substituted TPE derivatives were synthesized and used to separate mixtures of E / Z isomers by common column chromatography with high yields, as confirmed by single crystal analysis, mass spectrometry and NMR spectroscopy. The structure-property relationships of these molecules were systematically investigated by a combination of spectroscopic methods, theoretical calculations and single crystal data analysis. E / Z isomers exhibit many different fluorescent properties, such as AIE and mechanochromic behavior. Moreover, the position of N on the substituted pyridine ring also has an effect on the molecule stack pattern and the fluorescent properties. Collectively, our findings could not only improve the fundamental understanding of the cis / trans isomerization and photophysical properties of TPE derivatives but also provide a good strategy for designing different substituted groups that can produce various functions and have more potential applications. The intermolecular interactions and molecular packing form of fluorescent molecules have a huge impact on their optical properties, especially for AIE molecules.