Role of Electron-Donating and Electron-Withdrawing Groups in Tuning the Optoelectronic Properties of Difluoroboron-Napthyridine Analogues.

Five napthyridine-based fluorine-boron (BF-napthyridine) conjugated compounds have been theoretically designed, and subsequently, their photophysical properties are investigated. The influence of electron-donating and electron-withdrawing groups attached with the NCO moiety of BF-napthyridine molecule has been interpreted. The optoelectronic properties, including absorption spectra and emission spectra of the BF-napthyridine derivatives are studied using density functional theory (DFT) and time-dependent density functional theory (TD-DFT) based methods. Different characteristics, such as HOMO-LUMO gap, molecular orbital density, ionization potential, electron affinity, and reorganization energy for hole and electron, are calculated. All these molecules show excellent π-electron delocalization. TD-DFT results illustrate that the amine-substituted BF-napthyridine derivative has the highest absorption and emission maxima; it also shows a maximum Stoke shift. These results are well-correlated with the structural parameters and calculated HOMO-LUMO gap. Moreover, it is found that introduction of an electron-donating group into the BF-napthyridine complex improves the hole transport properties and provides useful clues in designing new materials for organic light emitting diodes (OLED). As a whole, this work demonstrates that electron-donating and electron-withdrawing groups in BF derivatives can extend their effectiveness toward designing of OLED materials, vitro cellular studies, ex vivo assays, and in vivo imaging agents.