Citation

BibTex format

@article{Fei:2015:10.1021/jacs.5b02785,
author = {Fei, Z and Boufflet, P and Wood, S and Wade, J and Moriarty, J and Gann, E and Ratcliff, EL and McNeill, CR and Sirringhaus, H and Kim, JS and Heeney, M},
doi = {10.1021/jacs.5b02785},
journal = {Journal of the American Chemical Society},
pages = {6866--6879},
title = {Influence of backbone fluorination in regioregular poly(3-alkyl-4-fluoro)thiophenes},
url = {http://dx.doi.org/10.1021/jacs.5b02785},
volume = {137},
year = {2015}
}

RIS format (EndNote, RefMan)

TY  - JOUR
AB - We report two strategies toward the synthesis of 3-alkyl-4-fluorothiophenes containing straight (hexyl and octyl) and branched (2-ethylhexyl) alkyl groups. We demonstrate that treatment of the dibrominated monomer with 1 equiv of alkyl Grignard reagent leads to the formation of a single regioisomer as a result of the pronounced directing effect of the fluorine group. Polymerization of the resulting species affords highly regioregular poly(3-alkyl-4-fluoro)thiophenes. Comparison of their properties to those of the analogous non-fluorinated polymers shows that backbone fluorination leads to an increase in the polymer ionization potential without a significant change in optical band gap. Fluorination also results in an enhanced tendency to aggregate in solution, which is ascribed to a more co-planar backbone on the basis of Raman and DFT calculations. Average charge carrier mobilities in field-effect transistors are found to increase by up to a factor of 5 for the fluorinated polymers.
AU - Fei,Z
AU - Boufflet,P
AU - Wood,S
AU - Wade,J
AU - Moriarty,J
AU - Gann,E
AU - Ratcliff,EL
AU - McNeill,CR
AU - Sirringhaus,H
AU - Kim,JS
AU - Heeney,M
DO - 10.1021/jacs.5b02785
EP - 6879
PY - 2015///
SN - 1520-5126
SP - 6866
TI - Influence of backbone fluorination in regioregular poly(3-alkyl-4-fluoro)thiophenes
T2 - Journal of the American Chemical Society
UR - http://dx.doi.org/10.1021/jacs.5b02785
UR - https://pubs.acs.org/doi/10.1021/jacs.5b02785
UR - http://hdl.handle.net/10044/1/23525
VL - 137
ER -