1. Synthesis
The Synthesis subgroup of MAFOHT focuses on the design and synthesis of novel self-assembling conjugated molecules, macromolecules and hybrid nanomaterials, and their use in a range of functional applications, including optical, electronic and catalytic materials. We are especially concerned with the preparation of such materials by developing new ecosustainable synthetic strategies based on combined ‘enabling techniques’ (i.e. microwave acceleration, heterogeneous catalysis, metal free coupling organic reactions).
1.1 π-conjugated and Hybrid materials
Tailoring of HOMO-LUMO energy levels, band gaps, self-organization, morphology and optoelectronic properties of π-conjugated oligomers is pursued by virtue of proper molecular design. Well-defined chemical constraints such as regiospecific substitution, chirality, scaffolding agents are investigated as tools to modulate electronic and self-assembly properties simultaneously (Org. Lett. 2008, 3665, Chem Eur. J. 2007, 10046, Chem. Phys. Chem 2007, 2621, Chem. Eur. J. 2006, 7304).
Fine
positioning of π-conjugated optically active segments is also promoted by
covalent bonding to selected nanotemplates (i.e. polymers, silica
nanoparticles, graphene oxide sheets, J. Chromat. A, 2009 in press…). The
subsequent further assembly of these nanomaterials in one-, two- and three
dimensional structure can be applied to afford materials with enhanced
functionalities for applications as nanoreactors, catalysts or in
nanotechnology devices.
Bio-conjugation of thiophene-based semiconductors with oligonucleotides is investigated as a new strategy to obtain target biohybrid nanostructures with synergetic properties for biosensing applications (Chem. Eur. J. 2008, 517 and 2009, 1876). Here, the predictable self-assembly of biomolecules is exploited to drive the organization of electroactive moieties into supramolecular multifunctional 2D and 3D structures. Collaborations with bio- subgroup….
1.3 Microwave assisted synthesis
Microwave
assisted (MW) synthetic methodologies are largely employed for the
preparation of
p-conjugated
molecules (Green Chem. 2008, 517), nanoparticles synthesis and surface
functionalization (manuscripts in prep.). Heterogeneous Pd catalyzed Suzuki
cross-coupling reaction have been developed to prepare metal-free, highly
pure materials in high yields, short reaction time (5 minutes vs. hours,
Green Chem. 2009, submitted) and efficient catalyst turnover.
1.4.
Thiophene-based fluorophores (link to Mediteknology)
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