Chun-yu CUI, Xiao-yang QIU, Qi QI, et al. Synthesis, Crystal Structure and Spectroscopic Properties of Novel Bisthiophene Derivatives. [J]. Chinese Journal of Luminescence 41(7):809-818(2020)
DOI:
Chun-yu CUI, Xiao-yang QIU, Qi QI, et al. Synthesis, Crystal Structure and Spectroscopic Properties of Novel Bisthiophene Derivatives. [J]. Chinese Journal of Luminescence 41(7):809-818(2020) DOI: 10.37188/fgxb20204107.0809.
Synthesis, Crystal Structure and Spectroscopic Properties of Novel Bisthiophene Derivatives
A series of bisthiophene derivatives were synthesized by Suzuki coupling reaction
in which bromine atoms on bisthiophene raw materials were substituted with different groups: 3-(5'-bromo-[2
2-bisthiophene]-5-yl)pyridine(C
13
H
8
BrNS
2
M
r
=322.24
compound Dt-1)
5
5-bis(pyridine-3)-yl)-2
2-bisthiophene(C
18
H
12
N
2
S
2
M
r
=320.43
compound Dt-2)
5-(3
5-bis (trifluoromethyl)phenyl) -2
2-bisthiophene(C
16
H
8
F
6
S
2
M
r
=378.35
compound Dt-3)
5
5-bis(3
4
5-trifluoro-phenyl)-2
2-bithiophene(C
20
H
8
F
6
S
2
M
r
=426.39
compound Dt-4). The structures were characterized by infrared spectroscopy(IR)
mass spectrometry(MS)
nuclear magnetic resonance spectroscopy(
1
H NMR) and single crystal X-ray diffraction. The luminescence properties were studied by UV-Vis absorption spectroscopy and fluorescence spectroscopy. The results showed that compound Dt-1 had strong fluorescence emission ranging from 390 nm to 470 nm under the excitation light of 349 nm in CH
2
Cl
2
solution
and the two largest emission peaks are 403 nm and 422 nm
respectively. Compound Dt-2 showed strong fluorescence emission in the 400-480 nm region under the excitation light of 372 nm with two maximum emission peaks at 430 nm and 440 nm. Compound Dt-3 exhibited the strongest fluorescence emission at 418 nm under excitation light of 350 nm and compound Dt-4 presented the strongest fluorescence emission at 436 nm under 371 nm excitation light. Due to the introduction of electron-withdrawing/donating groups in the conjugated structure of bisthiophene
the mobility and conjugation degree of π electrons are increased
and the intermolecular interaction force is enhanced. Energy loss caused by vibration relaxation phenomenon and Stokes shift leads to the shifts of the maximum absorption peaks to the long wave direction.
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