Isophlorin derivatives: Structures and materials for n-Channel Organic Semiconductors

Abstract

DFT and NMR calculations performed on isophlorin (1) and their derivatives (2–10) show that the 4O and the trans 2O, 2S derivatives (2 and 5) are anti-aromatic. The presence of strong $\mathit{S}\dots \mathit{S}$ ${\mathrm{p}}_{\mathit{\pi }}\text{-}{\mathrm{p}}_{\mathit{\pi }}$ bonding interactions stabilizes the planar structure (5) compared to the non-planar cis-isomer (8). Isophlorins are predicted to have very low electron reorganization energies ( ${\mathit{\lambda }}_{\mathrm{electron}}\sim 0.10\text{eV}$ ) which remain unaffected by puckering through steric interactions or solvation in aqueous media. We predict isophlorins to be the ideal candidates for n-Channel organic conductors.