Journal
ORGANIC FIELD-EFFECT TRANSISTORS VI
Volume 6658, Issue -, Pages -Publisher
SPIE-INT SOC OPTICAL ENGINEERING
DOI: 10.1117/12.731158
Keywords
pentacene; crystal engineering; anthradithiophene; soluble semiconductor
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Electronic devices based on organic materials have been an area of intense research for the past several years. Pentacene, an oligoacene, is regarded as a benchmark due to its high charge carrier mobility. However it has poor solubilty, un-optimized pi-overlap and is highly unstable. We have successfully demonstrated that peri-functionalization with trialkylsilyl ethynyl groups enhances the pi-stacking, solubility and stability of pentacene and related compounds. TIPS pentacene exhibits both two dimensional (2D) pi-stacking and good solubilty in common organic solvents. However changing the solubilizing groups or functionalizing the acene core results in a disruption of the desired 2D pi-stacking. Molecules with one dimensional (ID) pi-stacking have poorer mobility than those with 2D pi-stacking and hence larger solubilizing groups are required to change the a-stacking to 2D. The emphasis of this paper is to show how small changes in substitution can disrupt a-stacking in these molecules and how one can achieve the desired pi-stacking by careful selection of solubilzing groups.
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