Transcript Slide 1

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 52242 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 πsystems and π-π interactions in the solid state.
ex)
conclusions
Reported structures with thiophene and carboxylic-pyridine synthon
3
2
Pentacene
S
S
S
S
Future Work
S
S
Sexithiophene
OS tend to crystallize in an edge-to-face fashion
instead of ideal face-to-face fashion.
Pyridyl containing OSC
Carboxylic Functionalized SCCF
O
N
S
O
OH
benzoic acid
face-to-face
edge-to-face
(Beta-PET)•(Benzoic acid)
2.595(2) Ȧ
semiconductor
building block
(SBB)
handle
1
N
N
R
Semiconductor
Co-Crystal Former
(SCCF)
O H
N
R
O H
N
N
N
Semiconductor
Co-Crystal Former
(SCCF)
handle
semiconductor
building block
(SBB)
S
S
recognition sites
H O
Semiconductor
Co-Crystal Former
(SCCF)
recognition sites
handle
N
2(Beta-PET) •(Succinic acid)
2.680(6) Ȧ
ICRU Fellowship
H O
H O
1. Sokolov, A. N.; Friscic, T.; MacGillivray, L. R. J. Am. Chem.
Soc. 2006, 128, 2806
2. 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
Acknowledgement
R
N
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 2anthracenecarboxylic acid
references
H O
R
O H
Succinic acid
X-RaY Crystal Structures
Our Approach
O H
OH
edge-to-face
Theory states that the achievement of long
range π-stacked OS molecules in the solid-state
should result in an increase in charge transport
handle
HO
O
beta-PET
face-to-face
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
Dr. Leonard R. MacGillivray
4.18 Ȧ
Joseph C. Sumrak
Semiconductor
Co-Crystal Former
(SCCF)
The MacGillivray Group
3.40 Ȧ