This talk will discuss the use of the terephthalate ester to control the photophysics and solid-state assembly of p-conjugated oligomers and polymers. The solution state spectra of donor-acceptor phenylene ethynylene oligomers can be manipulated solely by changing the inductive power of the alkoxy component on the terephthalate ester: the band gaps of oligomers with identical p-conjugated structures span a range of over 0.1 eV. This effect persists when applied to polymeric systems. In the oligomer series, the different terephthalate esters yield either bathochromic shifts or hypsochromic shifts in the solid-state spectra relative to their spectra in solution. Based on X-ray crystallography studies, this effect is due to backbone-sidechain aromatic interactions that can enforce or hinder backbone planarity depending on the quadropolar nature of the backbone and substituent in combination with the number, location, and length of solubilizing alkyl chains. Polymers containing heavily fluorinated aromatic side-chain substituents resist aggregation in spun-cast films. This work provides new approaches for band gap engineering and solid-state assembly in p-conjugated materials.

Terephthalate esters as a modular electron acceptors and solid state directors in conjugated materials

247th National Meeting (2014)

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