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25th July 2014
Paper of the Week
J. Org. Chem. 2014, 79, 6480-6489
Controlling the Charge Transfer in D-A-D Chromophores Based on Pyrazine Derivatives
A family of symmetrical donor-acceptor-donor chromophores bearing various electron-withdrawing groups were designed and synthesised. The benzene-based chromophores were synthesised via imine formation followed by Suzuki coupling reaction with the corresponding boronic acid (Scheme 1). Thiophene-based chromophores were synthesised by undergoing a Suzuki coupling first followed by reduction of the nitro groups and subsequent imine formation (Scheme 2).
Intramolecular charge transfer (ICT) was found for all the chromophores, with different ICT interactions arising due to the varying electron-withdrawing abilities of the central pyrazine derivatives (vide infra).
Results suggest that extending the conjugation of a pyrazine acceptor in an orthogonal direction to the D-A-D backbone can dramatically improve the ICT interactions. These findings can be used to help understand the structure-property relationship of pyrazine-based semiconductors and control the charge transfer in pyrazine derivatives for the construction of low band gap materials.