Modification of firefly cyclic amino oxyluciferin analogues emitting multicolor light for OLED and near-Infrared biological window light for bioluminescence imaging: A theoretical study

Abstract

Abstract Quantum chemistry methods are used to investigate the effect of double bond and −F group on the electronic structure, optical properties of a series of firefly oxyluciferin analogues. The calculations show that insert of double bond largely increases the energy of HOMO and EA values, decreases the energy of LUMO and IP values hence improves the ability of hole and electron injection. The substituent of −F group largely decreases the energy of LUMO and increase EA values hence improves the electron injection ability. More important, the emission wavelength in gas phase range from 459 to 640 nm. Especially, cycoxyluc1a, cycoxyluc2a and cycoxyluc3a can be used as blue light-emitting materials. In DMSO, the emission maxima have a large red shift by about 121–213 nm compared to those in vacuum . The fluorescent scope of the studied compounds except for cycoxyluc1a, cycoxyluc2a and cycoxyluc3a is 665–853 nm, termed near-infrared region, is suitable for noninvasive biological imaging. Thus, the introduction of double bond and −F group is effective approach to obtain highly efficient multicolor light-emitting materials for OLED and near-infrared light-emitting materials for bioluminescence imaging.