Topological Control of Columnar Stacking Made of Liquid-Crystalline Thiophene-Fused Metallonaphthalocyanines.
The spontaneous organization of two-dimensional polyaromatic molecules into well-defined nanostructures through noncovalent interactions is important in the development of organic-based electronic and optoelectronic devices. Two regioisomers of thiophene-fused zinc naphthalocyanines ZnTNcendo and ZnTNcexo have been designed and synthesized to obtain photo- and electroactive liquid crystalline materials. Both compounds exhibited liquid crystalline behavior over a wide temperature range through intermolecular π-π interactions and local phase segregation between the aromatic cores and peripheral side chains. The structural differences between ZnTNcendo and ZnTNcexo affected the stacking mode in self-assembled columns, as well as symmetry of the two-dimensional rectangular columnar lattice. The columnar structure in liquid crystalline phase exhibited an ambipolar charge-transport behavior.
Division of Chemistry and Materials Faculty of Textile Science and Technology Shinshu University Ueda 386-8567 Japan.
Hiroyuki
H
Suzuki
National Institute of Advanced Industrial Science and Technology Kansai-Center 1-8-31 Midorigaoka, Ikeda Osaka 563-8577 Japan.
Koki
K
Kawano
Division of Chemistry and Materials Faculty of Textile Science and Technology Shinshu University Ueda 386-8567 Japan.
Kazuchika
K
Ohta
National Institute of Advanced Industrial Science and Technology Kansai-Center 1-8-31 Midorigaoka, Ikeda Osaka 563-8577 Japan.
Yo
Y
Shimizu
Division of Chemistry and Materials Faculty of Textile Science and Technology Shinshu University Ueda 386-8567 Japan.
Nagao
N
Kobayashi
Division of Chemistry and Materials Faculty of Textile Science and Technology Shinshu University Ueda 386-8567 Japan.
Mutsumi
M
Kimura
carrier mobility; charge transport; columnar stacking; dyes/pigments; liquid crystalline; phthalocyanines