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. 2022 Jun 9;25(1):136-147.
doi: 10.1080/15685551.2022.2086413. eCollection 2022.

Synthesis and characterization of some novel polythiophene derivatives containing pyrazoline

Vu Quoc Trung  1 , Tran Thi Thuy Duong  2 , Nguyen Thi Dua  1 , Nguyen Ngoc Linh  3 , Lai Dang Cuong  4 , Dao Phuong Thao  4 , Vo Khac Huy  5 , Nguyen Hoang Ha Phuong  6 , Nguyen Hien  1 , Duong Khanh Linh  1 , Vu Quoc Manh  3 , Nguyen Thuy Chinh  7   8 , Thai Hoang  7   8 , Luc Van Meervelt  9
Affiliations

Synthesis and characterization of some novel polythiophene derivatives containing pyrazoline

Vu Quoc Trung et al. Des Monomers Polym. .

Abstract

Eight polythiophene derivatives containing pyrazoline side groups were synthesized by a chemical oxidative coupling polymerization using FeCl3. The crystal structures of four monomers were determined which confirm the almost perpendicular orientation of the thiophene and pyrazoline rings, while the other substituents are more coplanar. Analyses of IR, 1H-NMR, Raman and UV-Vis spectra demonstrated that the suggested polymerization was successful to generate the synthesized polythiophenes with the expected structures. The morphology of the synthesized polythiophenes was studied by SEM. The different substituents attached to the 1- and 3-positions of the pyrazoline side chain led to differences in optical properties, electrical conductivity, and thermal stability of the synthesized polythiophenes. By adding a pyrazoline side chain to polythiophenes, some polymers achieve good solubility, electrical conductivity of about 1.3 × 10-6 S/cm, high fluorescence intensity (above 40,000 a.u.) at 505-550 nm and thermal stability up to 590°C in the air.

Keywords: Polythiophene derivatives; chemical polymerization; crystal structure; pyrazoline heterocycle.

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Conflict of interest statement

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Figures

Figure 1.
Figure 1.
The molecular structure of monomers (a) 1b, (b) 1d, (c) 2b and (d) 2d with displacement ellipsoids drawn at the 50% probability level. For 2b and 2d the minor components of the disordered thiophene rings are shown in blue.
Figure 2.
Figure 2.
IR spectra of polymers 3a–3d (left) and polymers 4a–4d (right).
Figure 3.
Figure 3.
IR spectra of monomer 2c and polymer 4c.
Figure 4.
Figure 4.
1H-NMR spectra of monomer 1d and polymer 3d.
Figure 5.
Figure 5.
UV-Vis spectra of synthesized polymers 3a–3d (left) and polymers 4a–4d (right).
Figure 6.
Figure 6.
FE-SEM images of the synthesized polythiophenes.
Figure 7.
Figure 7.
TGA and DTA (inset) thermograms of synthesized polymers 3a–3d (left) and polymers 4a–4d (right).
Figure 8.
Figure 8.
Photoluminescence spectra of synthesized polymers 3a–3d (left) and polymers 4a–4d (right).
Figure 9.
Figure 9.
Conductivity of synthesized polymers 3b, 3c, 3d, 4c.
Scheme 1.
Scheme 1.
Synthesis of polythiophene containing polythiophene derivatives bearing pyrazoline.
See this image and copyright information in PMC

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