Acta Phys. -Chim. Sin. ›› 2012, Vol. 28 ›› Issue (12): 2944-2952.doi: 10.3866/PKU.WHXB201208012

• PHOTOCHEMISTRY AND RADIATION CHEMISTRY • Previous Articles     Next Articles

Synthesis and Characterization of New 1,3,5-Triazine-Based Compounds Exhibiting Aggregation-Induced Emission and Mechanochromism

OUYANG Mi, YU Chun-Hui, ZHANG Yu-Jian, HU Bin, Lü Xiao-Jing, SUN Jing-Wei, ZHANG Cheng   

  1. State Key Laboratory Breeding Base for Green Chemistry Synthesis Technology, College of Chemical Engineering and Material Science, Zhejiang University of Technology, Hangzhou, 310014, P. R. China
  • Received:2012-06-26 Revised:2012-07-30 Published:2012-11-14
  • Supported by:

    The project was supported by the National Key Basic Research Program of China (973) (2010CB635108, 2011CBA00700) and International S & T Cooperation Program, China (2012DFA51210).

Abstract:

Two star-shaped molecules consisting of a 1,3,5-triazine core with peripheral tetraphenylethylene moieties, 2,4,6-tris(4-(1,2,2-triphenylvinyl)phenyl)-1,3,5-triazine (TTPE-Tr) and 2,4,6-tris(4-(1,2,2- triphenylvinyl)- [1,1-biphenyl]-4-yl)-1,3,5-triazine (TTPE-Ph-Tr), have been synthesized. These compounds were characterized by nuclear magnetic resonance spectroscopy (NMR), matrix assisted laser desorption/ionization-mass spectrometry (MALDI-MS) and elemental analysis. Both compounds exhibited aggregation-induced emission enhancement (AIEE) properties during addition of water to their tetrahydrofuran (THF) solutions. Results from UV-Vis spectroscopy, photoluminescence (PL) spectroscopy, and scanning electron microscopy (SEM) demonstrated that the restricted intra-molecular bond rotation (RIR) reduced non-radiative transitions in these compounds in the aggregated state, resulting in the fluorescence quantum yields (ΦF) increase. TTPE-Tr was also found to display mechanofluorochromic behavior. This compound, a blue-green powder (ΦF=24.4%, λem=508 nm), exhibited relatively weak yellow/green emission (ΦF=14.7%, λem=517 nm) upon grinding. The phase transition process responsible for this mechanochromism was confirmed by PL spectroscopy, X-ray diffraction (XRD) and time-resolved fluorescence spectroscopy. Thermal analysis of TTPE-Tr and TTPE-Ph-Tr showed that these compounds possess excellent thermal stability, with decomposition temperatures of 464 and 385℃, respectively.

Key words: 1,3,5-Triazine, Tetraphenyl-ethylene, Aggregation-induced emission enhancement, Mechanochromism, Thermal stability

MSC2000: 

  • O644