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25th July 2014

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).

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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.

 

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