4.6 Article

Derivatives of 1-benzyl-4-(4-triphenylvinylphenyl) pyridinium bromide: Synthesis, characterization, mechanofluorochromism/aggregation-induced emission (AIE) character and theoretical simulations

Journal

JOURNAL OF LUMINESCENCE
Volume 195, Issue -, Pages 14-23

Publisher

ELSEVIER SCIENCE BV
DOI: 10.1016/j.jlumin.2017.11.005

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Funding

  1. National Key Research and Development Program of China [2016YFB0303805]
  2. Science and Technology Fundation of Educational office of Jilin Province [JJKHZ-2016-361]
  3. Natural Science Fundation from Jilin Scientific and Technological Development Program [20170101190JC]
  4. Science and Technology Innovation Fundation of Changchun University of Science and Technology [XJJLG-2015-05]
  5. Zhejiang provincial Collaborative Innovation Center of Agricultural Biological Resources Biochemical Manufacturing [2016KF0006]

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4-(4-triphenylvinyl phenyl) pyridine (TPEPy) was used, along with the benzile bromide derivatives, to prepare 1-benzyl-4-(4-triphenylvinyl phenyl) pyridinium bromide (1) and its derivatives by replacing the benzyl bromide with 4-cyanobenzyl bromide for 2, 4-nitrobenzyl bromide for 3 and 4-trifluoromethyl benzyl bromide for 4, respectively. The maxima of the photoluminescent (PL) spectra of the freshly prepared powder samples of 1 similar to 4 are in the range of 510 nm similar to 530 nm with the absolute luminescence quantum yields (ALQY) of 88.10% for 1, 4.69% for 2, 1.70% for 3 and 36.30% for 4, respectively, which would redshift to the range of 554 nm similar to 571 nm with ALQYs of 54.70% for 1, 41.00% for 2, 14.70% for 3 and 43.40% for 4, respectively, after they are ground. At the same time, 1 similar to 4 have no obvious PL bands in dichlormethane solution (10-5 mol/L) until >= 80% n-hexane was added. Finally, the ground-state geometries and the UV-Vis absorption spectra of 1 similar to 4 were simulated at B3LYP/6-31G(d, p) level to theoretically explain their photophysical behaviors.

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