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The effect of regioisomerism on the crystal packing and device performance of desymmetrized anthradithiophenes
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. Cy...
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Published in: | Journal of materials chemistry. C, Materials for optical and electronic devices Materials for optical and electronic devices, 2015-01, Vol.3 (34), p.8956-8962 |
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Main Authors: | , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | 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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ISSN: | 2050-7526 2050-7534 |
DOI: | 10.1039/C5TC02145F |