期刊
MATERIALS CHEMISTRY FRONTIERS
卷 2, 期 6, 页码 1126-1136出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8qm00008e
关键词
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资金
- Natural Science Foundation of China [21672023, 21472012, 21525523, 21722507, 21574048]
- Thousand Youth Talents Plan of China
- National Basic Research Program of China (973 Program) [2015CB932600]
- National Key R&D Program of China [2017YFA0208000, 2016YFF0100800]
A series of branched -conjugated small molecular red fluorescent probes (TTE-4TPA, TTE-4DPT and TTE-4DTPA) with aggregation-enhanced emission (AEE) characteristics have been synthesized for mechanochromic applications and cell imaging. These red fluorescent probes possess the same 1,1,2,2-tetra(thiophen-2-yl)ethene (TTE) core unit, but different branched terminal groups (triphenylamine (TPA), N,N-diphenylthiophen-2-amine (DPT), and N,N-diphenyl-4-vinylaniline (DTPA)). The photophysical properties, mechanochromic properties, and cell imaging behaviour based on these three red fluorescent probes are investigated. Absorption and emission spectra of TTE-4DPT and TTE-4DTPA showed obvious red-shifts by replacing TPA units with DTPA and DPT terminal groups owing to the enhanced -conjugation of the molecule and more extended skeletons in comparison to TTE-4TPA. However, TTE-4TPA exhibited the highest fluorescence quantum efficiency of ca. 11% with the highest (AIE) in the solid state owing to the most crowded skeletons. TTE-4TPA showed dramatic mechanochromic behaviour (from yellow to deep red powder) with extraordinary red shifts of fluorescence peaks (ca. 110 nm) after grinding. In contrast, TTE-4DPT exhibited a weak mechanochromic response with slight red shift after grinding. The powder X-ray diffraction (XRD) and differential scanning calorimetry (DSC) experiments indicated that the mechanochromic mechanism is associated with a morphology change from the more loose crystalline state of TTE-4TPA and TTE-4DPT to the more compact amorphous state. Interestingly, the amorphous state of TTE-4DTPA is a promising cell membrane specific staining AEE probe with low cytotoxicity and excellent photostability. Rainbow imaging and three-dimensional imaging experiments were carried out to further prove the cell membrane specific staining property of TTE-4DTPA. These results demonstrated that the strategy for construction of red fluorescent probes with a TTE core and branched TPA analogue terminal groups not only has achieved AEE characteristics with high fluorescence quantum efficiency, but also has resulted in an excellent mechanochromic probe and a highly photostable cell membrane specific staining probe.
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