Organic p-conjugated oligomers and polymers can mutually provide superstructural control and appropriate optoelectronic properties needed for the construction of semiconductor-based optoelectronic devices. A limited number of building blocks offer the necessary built-in molecular recognition features. Accordingly, presented is the incorporation of nucleobases in linear p-conjugated oligomers to serve as leverage for tuning the bulk properties. Explored is the extent to which 'information-rich' molecular structure might translate into rationally tunable, or improved, application-relevant parameters.  Structure-property relationships have been established for a set of nucleobase-terminated oligomers. The absorption and emission profiles reflect the electronic structure of the nucleobase (e.g., adenine vs. guanine) and the p-linker. Donor-acceptor-donor systems are created by introducing a benzo[c][1,2,5]thiadiazole group, resulting in lower band gaps compared to terthiophene-linked nucleobases (?E ~ 1.9 eV vs. 2.3 eV). The oligomer redox properties and HOMO-LUMO energies show a dependence on the nature of the nucleobase, in agreement with B3LYP/6-311+G* calculations.

Optical properties and electronic structures of purine-containing π-conjugated oligomers

245th National Meeting (2013)

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