Effects of electron withdrawing groups on transfer integrals, mobility, electronic and photo-physical properties of naphtho[2,1-b:6,5-b ']difuran derivatives: a theoretical study

Abstract

New derivatives of naphtho[2,1-b:6,5-b ]difuran (DPNDF) have been designed by attaching different electron withdrawing groups (EWGs) (including –COOH, –OCF3 and –CN). The molecular structures of all derivatives have been optimized at the ground (S 0) and first excited (S 1) states using density functional theory (DFT) and time-dependent density functional theory (TD-DFT), respectively. The highest occupied molecular orbitals (HOMOs), the lowest unoccupied molecular orbitals (LUMOs), photophysical properties, adiabatic/vertical electron affinity (EAa)/(EAv), adiabatic/vertical ionization potential (IPa)/(IPv) and hole/electron reorganization energies λh/λe have been investigated. Transfer integral, mobility and stability have also been calculated. Electron mobility as high as 5.148 cm2 V–1 s–1 has been obtained. Upon substituting the EWGs electron transfer integrals are boosted in newly designed derivatives. The balanced hole and electron reorganization energies, and the improved transfer integrals lead to enhanced mobility in the derivative with COOH groups. Thus the latter compound would be an efficient electron transfer material. Photo-stability of furan based materials is enhanced by introducing the EWGs at different positions.