Abstract
A series of selenophene oligomers incorporating conjugated fluorinated phenylene units have been synthesised as potential semiconductor materials for organic field-effect transistors (OFETs). X-ray crystallography shows that the molecules are held in close proximity by several short intermolecular contacts, making them ideal candidates for OFET applications.
Highlights
Functionalised oligothiophenes are studied intensively owing to their potential use in a variety of devices such as organic field-effect transistors (OFETs),[1,2,3,4] photodiodes,[5,6,7] light-emitting diodes,[8,9,10] and their integrated devices.[11]
For example Facchetti et al[13] have demonstrated that structures such as 1 are excellent OFET materials
We recently reported a series of compounds (2–4) bearing a central tetrafluorophenylene unit.[15,16]
Summary
Functionalised oligothiophenes are studied intensively owing to their potential use in a variety of devices such as organic field-effect transistors (OFETs),[1,2,3,4] photodiodes,[5,6,7] light-emitting diodes,[8,9,10] and their integrated devices.[11]. We recently reported a series of compounds (2–4) bearing a central tetrafluorophenylene unit.[15,16] The noncovalent interactions of the fluorine atoms with components on adjacent thiophene rings result in highly planar structures in the solid state, together with excellent solubility of the oligomers and corresponding polymers in common organic solvents. The exact nature of the p–p associations can be seen in Figure 2 (bottom) which shows the interaction of the tetrafluorophenylene unit with two selenophene heterocycles This slip-stack, alternate arrangement has been observed previously[15,16] and is well-known for benzene–perfluorobenzene cocrystals,[25,26,27] in which the tetrafluorobenzene ring has inversed electron density distribution and participates in electrostatic interactions with electron-rich aromatic rings. For 8, the spectrum consists of a single, broad band with a maximum at 497 nm
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