Citation: BAI Xiang-Yang, SHI Cheng-Cheng, SUN Yuan, DING Rui, HUANG Jian-Yan, YANG Jia-Xiang. Bromine-contained and Modified with Amino Group, D-π-Aα-Cyanostilbenzene Derivative: Synthesis, Crystal Structure and Photoluminescence[J]. Chinese Journal of Structural Chemistry, ;2016, 35(9): 1362-1368. doi: 10.14102/j.cnki.0254-5861.2011-1106 shu

Bromine-contained and Modified with Amino Group, D-π-Aα-Cyanostilbenzene Derivative: Synthesis, Crystal Structure and Photoluminescence

1.
College of Chemistry & Chemical Engineering, Anhui University, Hefei 230601, China

Received Date: 30 December 2015
Available Online: 6 April 2016
Fund Project: Supported by the Educational Commission of Anhui Province(KJ2014ZD02) the National Natural Science Foundation of China(51432001) (KJ2014ZD02)

A novel D-π-A type α-cyanostilbenzene derivative,(Z)-2-(4-aminophenyl)-3-(4-bromophenyl)-acrylonitrile(ABAN), was designed and synthesized, by introducing an electrondonating amino group and a heavy atom. The structure of ABAN was confirmed by FT-IR, ¹H NMR, ¹³C NMR spectra and single-crystal X-ray diffraction analysis. The ABAN is of orthorhombic system, space group P2₁2₁2₁, with a=8.6100(14), b=9.6923(16), c=15.705(3)Å, M_r=299.17, V=1310.6(4)Å³, Z=4, D_c=1.516 g/cm^-3, μ=3.119 mm^-1, F(000)=600, R_int=0.038, R(I>2σ(I))=0.0276, wR(I>2σ(I))=0.0628, R(all data)=0.0324, wR(all data)=0.0646, completeness to theta=25.00 was 99.8% and GOOF=1.04. In the crystal structure, ABAN molecules were linked with each other through intermolecular C-H…π interactions and N-H…N hydrogen bonds, by which the 1D chain, 2D plane and 3D stacking structures were constructed. The photophysical properties and calculation results confirmed that ABAN possessed an intramolecular charge transfer(ICT) process. ABAN could be applied into the optoelectronic material field due to good solvent-tuned photophysical properties and highly thermal stability.
- bromine,
- amino group,
- crystal structure,
- photophysical properties
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