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3126097 
Journal Article 
Theoretical Investigation on Firefly Oxyluciferin Analogs Bearing an Amino Group Used as Organic Light-Emitting Diodes Materials 
Min Chungang; Li Zuosheng; Cui Xiaoying; Yang Xikun; Huang Shaojun; Wang Shaohua; Ren Aimin 
2015 
1 
Youji Huaxue / Chinese Journal of Organic Chemistry
ISSN: 0253-2786 
Science Press 
35 
2 
432-438 
Chinese 
WOS:000351492400017 
Firefly oxyluciferin has great potential application in organic light-emitting devices, because of the high efficiency and wide range of multicolor light from green to red. To gain an insight into the structure-property relationships, a set of firefly oxyluciferin analogs bearing an amino group with benzopyran, biphenyl, bipyridine, phenanthrene, phenanthroline, fluorine and coronene instead of benzothiazole ring were designed. In this study, a systematic investigation into them was carried out using the density functional theory and time-dependent density functional theory methods. The calculated values show that bipyridylaminooxyluciferin (BPAOL) and orthophenanthrolylaminooxyluciferin (PMAOL) with nitrogen atom have smaller the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energies, larger ionization potential (IP) and electron affinity (EA) values than biphenylaminooxyluciferin (BIAOL) and phenanthrylaminooxyluciferin (PHAOL) with carbon atom. Compound aminooxyluciferin (AOL), BIAOL, BPAOL, PHAOL, PMAOL, fluorenylaminooxyluciferin (FLAOL) and coronenylaminooxyluciferin (COAOL) can be used as electron-injection/transporting materia ls. AOL, PHAOL, FLAOL and COAOL can be used as blue light-emitting materials. These results indicate that the firefly oxyluciferin analogs bearing an amino group have many interesting properties and are good candidates for optoelectronic application. © 2015 Chinese Chemical Society & SIOC, CAS. 
ionization potential and electron affinity; reorganization energy; oxyluciferin analogs; emission spectrum; time-dependent density functional theory