TY - JOUR
T1 - The effect of regioisomerism on the crystal packing and device performance of desymmetrized anthradithiophenes
AU - Hallani, Rawad K.
AU - Thorley, Karl J.
AU - Hailey, Anna K.
AU - Parkin, Sean R.
AU - Loo, Yueh Lin
AU - Anthony, John E.
N1 - Publisher Copyright:
© The Royal Society of Chemistry 2015.
PY - 2015/7/31
Y1 - 2015/7/31
N2 - Anthradithiophenes (ADTs) are typically synthesized as inseparable mixtures of regioisomers. In this paper, we describe the synthesis of desymmetrized anthradithiophenes containing one trialkylsilylethyne solubilizing group, which allowed chromatographic separation of the three resulting isomers. Cyclic voltammograms, as well as absorption and emission spectra for all isomers, were nearly identical. However, X-ray crystallography revealed that the positions of the sulfur atoms in each isomer strongly influence crystal packing, corroborating calculations that show the S-π interaction to be less stabilizing than the C-H-π interaction. Isomer 3c packs in a pseudo 1-D fashion while isomers 3a and 3b pack as isolated π-stacked pairs. Isomer 3c shows a field-effect mobility four orders of magnitude higher than isomers 3a and 3b, presumably due to this difference in packing motif.
AB - Anthradithiophenes (ADTs) are typically synthesized as inseparable mixtures of regioisomers. In this paper, we describe the synthesis of desymmetrized anthradithiophenes containing one trialkylsilylethyne solubilizing group, which allowed chromatographic separation of the three resulting isomers. Cyclic voltammograms, as well as absorption and emission spectra for all isomers, were nearly identical. However, X-ray crystallography revealed that the positions of the sulfur atoms in each isomer strongly influence crystal packing, corroborating calculations that show the S-π interaction to be less stabilizing than the C-H-π interaction. Isomer 3c packs in a pseudo 1-D fashion while isomers 3a and 3b pack as isolated π-stacked pairs. Isomer 3c shows a field-effect mobility four orders of magnitude higher than isomers 3a and 3b, presumably due to this difference in packing motif.
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U2 - 10.1039/c5tc02145f
DO - 10.1039/c5tc02145f
M3 - Article
AN - SCOPUS:84939825270
SN - 2050-7534
VL - 3
SP - 8956
EP - 8962
JO - Journal of Materials Chemistry C
JF - Journal of Materials Chemistry C
IS - 34
ER -