Aggregation-induced emission compounds based on 9,10-dithienylanthracene and their applications in cell imaging.

Three new symmetrical 9,10-dithienylanthracene (DTA) derivatives, including 9,10-bis-(4-(4-methoxyphenyl)-5-methylthiophene-2-yl)anthracene (BMPTA), 9,10-bis-(5-methyl-4-phenylthiophene-2-yl)anthracene (BPTA), and 9,10-bis-(4-(4-cyanophenyl)-5-methylthiophene-2-yl)anthracene (BCPTA), with excellent aggregation-induced emission (AIE) behaviors had been designed and synthesized successfully. Crystal BMPTA and BPTA had nonplanar conformations because of the multiple intermolecular hydrogen bonding interaction between the adjacent molecules, which restricted their intramolecular rotation and enabled them to emit intensely. Additionally, both BMPTA and BPTA exhibited reversible mechanofluorochromic (MFC) performance by grinding-fuming, which was systematically investigated with powder X-ray diffraction (XRD), differential scanning calorimetry (DSC) and photoluminescent (PL) lifetime. The results showed that substituent groups had significant influence on their molecular packing, MFC and AIE properties. Furthermore, these DTA luminogens could be applied in cell imaging as fluorochrome. Three new symmetric 9, 10-dithienylanthracene (DTA) derivatives with remarkable aggregation-induced emission (AIE) characteristics have been synthesized. Their properties, including AIE, crystal structures, mechanofluorochromic, and cell imaging were investigated. Image 1 • Three new DTA derivatives with excellent AIE behavior had been designed and synthesized. • The crystal structures of BMPTA and PTA showed nonplanar conformations and reversible MFC performance by grinding-fuming. • All of them could be applied in cell imaging as fluorochrome. [ABSTRACT FROM AUTHOR]