Journal
MATERIALS
Volume 14, Issue 20, Pages -Publisher
MDPI
DOI: 10.3390/ma14206146
Keywords
poly(3-hexylthiophene); polythiophenes; oxidative polymerization; gel-permeation chromatography; high molecular weight; conductive polymers; order of addition; iron (III) chloride; alkyl-substituted EDOT; 3,4-dialkoxythiophene
Categories
Funding
- National Science Foundation Partnership for Research and Education in Materials [2122041]
- Texas State University Research Enhancement Program [9000002766]
- Texas State University Undergraduate Research Fellowship funding [9000002520, 9000002519, 9000002733]
- Division Of Materials Research
- Direct For Mathematical & Physical Scien [2122041] Funding Source: National Science Foundation
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In this study, several polythiophenes were synthesized using different oxidative methods, and the impact of these methods on the molecular weight and degree of polymerization of the polymers was compared. The results indicate that careful consideration of the oxidation potential of the monomer and solution is crucial for optimizing reaction conditions to achieve desired yield and degree of polymerization.
Polythiophenes (PTs) constitute a diverse array of promising materials for conducting polymer applications. However, many of the synthetic methods to produce PTs have been optimized only for the prototypical alkyl-substituted example poly(3-hexylthiophene) (P3HT). Improvement of these methods beyond P3HT is key to enabling the widespread application of PTs. In this work, P3HT and two ether-substituted PTs poly(2-dodecyl-2H,3H-thieno[3,4-b][1,4]dioxine) (PEDOT-C12) and poly(3,4-bis(hexyloxy)thiophene) (PBHOT) are synthesized by the FeCl3-initiated oxidative method under different conditions. Polymerization was carried out according to a common literature procedure ( reverse addition ) and a modified method ( standard addition ), which differ by the solvent system and the order of addition of reagents to the reaction mixture. Gel-permeation chromatography (GPC) was performed to determine the impact of the different methods on the molecular weights (M-w) and degree of polymerization (X-w) of the polymers relative to polystyrene standards. The standard addition method produced ether-substituted PTs with higher M-w and X-w than those produced using the reverse addition method for sterically unhindered monomers. For P3HT, the highest M-w and X-w were obtained using the reverse addition method. The results show the oxidation potential of the monomer and solution has the greatest impact on the yield and X-w obtained and should be carefully considered when optimizing the reaction conditions for different monomers.
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