Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (2): 432-438.DOI: 10.6023/cjoc201409003 Previous Articles     Next Articles



闵春刚a, 李作盛b, 崔小英a, 杨喜昆a, 黄绍军a, 王绍华a, 任爱民b   

  1. a 昆明理工大学分析测试研究中心 昆明 650093;
    b 吉林大学理论化学研究所 理论化学计算国家重点实验室 长春 130023
  • 收稿日期:2014-09-03 修回日期:2014-10-13 出版日期:2015-02-25 发布日期:2014-10-21
  • 通讯作者: 闵春刚, 任爱民;
  • 基金资助:

    国家自然科学基金(Nos. 21473071, 21173099, 21363012, 51363012, 51374117)、国家重点基础研究发展规划(973计划, No. 2013CB834801)、高校基础科学研究专项、云南省应用基础研究计划(No. 2011FZ040)、云南省教育厅科学研究基金(No. 2012Y545)、昆明理工大学人才培养基金(No. KKSY201232040)和吉林大学理论化学计算国家重点实验室开放课题基金资助项目.

Theoretical Investigation on Firefly Oxyluciferin Analogs Bearing an Amino Group Used as Organic Light-Emitting Diodes Materials

Min Chunganga, Li Zuoshengb, Cui Xiaoyinga, Yang Xikuna, Huang Shaojuna, Wang Shaohuaa, Ren Aiminb   

  1. a Research Center for Analysis and Measurement, Kunming University of Science and Technology, Kunming 650093;
    b State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University, Changchun 130023
  • Received:2014-09-03 Revised:2014-10-13 Online:2015-02-25 Published:2014-10-21
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21473071, 21173099, 21363012, 51363012, 51374117), the National Key Basic Research Program (973 Program, No. 2013CB834801), the Special Funding to Basic Scientific Research Projects for Central Colleges, the Applied Basic Research Plans Program of Yunnan Province (No. 2011FZ040), the Scientific Research Fund of Yunnan Provincial Education Department (No. 2012Y545), the Training Foundation for Talents of Kunming University of Science and Technology (No. KKSY201232040) and the Foundation of State Key Laboratory of Theoretical and Computational Chemistry.

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 materials. 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 ap-plication.

Key words: ionization potential and electron affinity, reorganization energy, oxyluciferin analogs, emission spectrum, time-dependent density functional theory