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Synthesis and Characterization of a Regioregular Side‐Chain Semifluorinated Polythiophene
Author(s) -
Horn Christoph,
Pospiech Doris,
Zessin Johanna,
Stein Sebastian,
Jehnichen Dieter,
Komber Hartmut,
Göbel Michael,
Voit Brigitte,
Kiriy Anton
Publication year - 2019
Publication title -
physica status solidi (a)
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.532
H-Index - 104
eISSN - 1862-6319
pISSN - 1862-6300
DOI - 10.1002/pssa.201800747
Subject(s) - side chain , polythiophene , thiophene , monomer , dispersity , polymerization , polymer chemistry , stacking , materials science , polymer , condensation polymer , chemistry , conductive polymer , organic chemistry , composite material
The synthesis of a new side‐chain semifluorinated thiophene monomer obtained by the reaction of 3‐thiophene ethanol with 4,4,5,5,6,6,7,7,8,8,9,9,9‐tridecafluorononan‐1‐ol is reported. The side‐chain semifluorinated monomer is polymerized using Kumada catalyst‐transfer polycondensation to obtain the regioregular side‐chain semifluorinated thiophene polymer P3sfT with a sufficiently high molar mass of about 26 000 g mol −1 and narrow dispersity Đ of 1.11. The bulk structure is analyzed by X‐ray scattering and shows π–π stacking as well as the strong formation of layer structures caused by the self‐organization of the semifluorinated side chains. The structure is even more pronounced than in P3HT which is due to the extension of the side chains by fluorinated methylene groups. Thin films are prepared from solution in octafluorotoluene and examined for their layer structure using XRR and 2D‐GIWAXS. The same structure as in solid state is found, again indicating high self‐organization of the semifluorinated side chains. Due to the high self‐assembly, the polymer shows potential as semiconductor in organic electronics. Measurements of electronic properties are currently in progress.