Marco Teiber and Thomas JJ Müller

Chemoenzymatic synthesis of oligo- and poly(terthiopenes)
Marco Teiber and Thomas J. J. Müller
Lehrstuhl für Organische Chemie, Institut für Organische Chemie und Makromolekulare Chemie,
Heinrich-Heine-Universität Düsseldorf
Marco Teiber
project started 01.10.09
Marco.Teiber@uni-duesseldorf.de
Introduction:
Oligomeric and polymeric π-conjugated molecules have
g y important
p
for applications
pp
in p
plastics
become increasingly
electronics, e.g. as organic light emitting diodes, organic
field effect transistors, and organic photovoltaics.
Besides the molecular properties, controlled by suitable
substitution pattern, selective chemical synthesis on the
basis of computations and physical measurements, the
control of the materials properties is a domain of the solid
state and to date very few reliable concepts necessitate the
search
h off new approaches.
h
Self-organization by π-stacking and weak polar interactions
with a minimum of byproducts for solid state packing under
kinetic control requires mild synthetic conditions.
Interestingly, the π-stack organization accounts for a
significant stabilization over the unfolded chain.
Fig 1: Computed π-stacking of terthiophenes (left) and
covalentlyy linked terthiophenes
p
((right)
g ) [[MMFF]]
According to computations an enhanced formation of a 3Dsuperstructure of the functional units such as oligothiophenes
should be achieved under the mild conditions of enzymatic
coupling.
Aims
• One-pot three-component syntheses of conjugated terthiophenes, quaterthiophenes, quinquethiophenes, and related
carbazole derivatives with ω-hydroxy carboxy or ω-amino carboxy functionality. Electronic characterization of the monomers by
optical and electrochemical methods
• The lipase catalyzed oligo- and polymerization to self-organizing polyesters and polyamides shall be developed and established
by systematic methodological studies.
• Characterization of the materials properties by optical and electrochemical methods, and in collaboration by scanning probe
and transmission electron microscopy.
• Development of electronic devices with the new materials in collaboration with physicists.
• Intended future collaboration
Strategy
• Using one-pot multi-component reactions
• Using enzymes to link the monomere-units
Results
• Successful synthesis of all products and intermediates as
references of the first test system by using classical methods
• First enzymatic reactions to link the terthiophene substrate
Fig 2: Classical step by step synthesis (top) and one-pot multicomponent-synthesis (bottom)
CLIB-Graduate Cluster Industrial Biotechnology: Project Presentation.