Citation: OUYANG Mi, YU Chun-Hui, ZHANG Yu-Jian, HU Bin, Lü Xiao-Jing, SUN Jing-Wei, ZHANG Cheng. Synthesis and Characterization of New 1,3,5-Triazine-Based Compounds Exhibiting Aggregation-Induced Emission and Mechanochromism[J]. Acta Physico-Chimica Sinica doi: 10.3866/PKU.WHXB201208012 shu

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

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 Date: 26 June 2012
Available Online: 1 August 2012
Fund Project: 国家重点基础研究发展规划(973)前期专项项目(2010CB635108, 2011CBA00700) (973)前期专项项目(2010CB635108, 2011CBA00700)国际科技合作重点项目计划(2012DFA51210)资助 (2012DFA51210)

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 (Φ_F) increase. TTPE-Tr was also found to display mechanofluorochromic behavior. This compound, a blue-green powder (Φ_F=24.4%, λ_em=508 nm), exhibited relatively weak yellow/green emission (Φ_F=14.7%, λ_em=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.
- 1,3,5-Triazine,
- Tetraphenyl-ethylene,
- Aggregation-induced emission enhancement,
- Mechanochromism,
- Thermal stability
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