1. X-RaY Crystal Structures
Co-crystallization of Thiophene-based Semiconductors with Carboxylic Acids and Effects on Crystal Packing
Kristin M. Kester, Joseph C. Sumrak and Leonard R. MacGillivray
Department of Chemistry, University of Iowa, Iowa City, IA USA.
Background
Carboxylic functionalized SCCF
Organic semiconductors (OS) are key to the development of light weight, flexible, and transparent electronics
Charge transport in OS occurs via a hopping mechanism between π-systems
Due to charge transportation mechanism ideal OS are molecules with large conjugated π-systems and π-π interactions in the solid state.
ex)
OS tend to crystallize in an edge-to-face fashion instead of ideal face-to-face fashion.
Theory states that the achievement of long range π-stacked OS molecules in the solid-state should result in an increase in charge transport
conclusions
Reported structures with thiophene and carboxylic-pyridine synthon
Carboxylic acids can also be used as hydrogen donors in our SCCF
The introduction of a SCCF induces a change in the crystal packing
SCCF affects pi-pi interactions between neighboring molecules
The interchanging of SCCF from our library allows for different modes of solid-state packing to be achieved 3 2
Future Work
Pyridyl containing OSC
Carboxylic Functionalized SCCF
Co-crystallize more SCCFs with different OSC. Focusing on SCCFs with multiple H-donor sites and OSC with multiple H-acceptors
Obtain crystal structures for OSC alone
Synthesize additional organic semiconductor building blocks
Obtain single-crystal mobility measurements of co-crystals and pure organic semiconductors
Collect crystal data for co-crystals obtained with PTETP and 2-anthracenecarboxylic acid
X-RaY Crystal Structures
2.595(2) Ȧ
(Beta-PET)•(Benzoic acid)
Our Approach 1
references
Sokolov, A. N.; Friscic, T.; MacGillivray, L. R. J. Am. Chem. Soc. 2006, 128, 2806
Sun , X.-Z., Zeng M.-H., Ye , B.-H. Acta Crystallogr.,Sect.E:Struct.Rep. 2004, 60, o2103
3. Morimoto, M., Irie, M. Chem.-Eur.J. 2006, 12, 4275
2.680(6) Ȧ
2(Beta-PET) •(Succinic acid)
Acknowledgement
ICRU Fellowship
Dr. Leonard R. MacGillivray
Joseph C. Sumrak
The MacGillivray Group
4.18 Ȧ
3.40 Ȧ