Acta Phys. -Chim. Sin. ›› 2015, Vol. 31 ›› Issue (10): 1971-1976.doi: 10.3866/PKU.WHXB201509011

• PHOTOCHEMISTRY AND RADIATION CHEMISTRY • Previous Articles     Next Articles

A Novel Molecule Based on 2, 2'-Dipyridylamine Functionalized 9, 9-Diarylfluorene with Steric Hindance: Design, Synthesis and Electro-Optical Property Research

Xiang-Hua. ZHAO1,*(),Xiao-Sheng. LI1,Li. ZHOU1,Na-Na. WU1,Xing-Kun. YANG1,Shun-Dong. YUAN2,Dong-Xue. DING3,Hui. XU3   

  1. 1 College of Chemistry and Chemical Engineering, Xinyang Normal University, Xinyang 464000, Henan Province, P. R. China
    2 College of Science, China University of Petroleum, Qingdao 266580, Shandong Province, P. R. China
    3 Key Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Heilongjiang University, Harbin 150080, P. R. China
  • Received:2015-06-01 Published:2015-10-10
  • Contact: Xiang-Hua. ZHAO
  • Supported by:
    the National Natural Science Foundation of China(61405170);Key Project of Education Department, Henan Province,China(14B150011);University Students Sustentation Fund of Xinyang Normal University, China(2014-DXS-136, 2015-DXS-163)


The bipolar molecule N-(4-(9-phenyl-fluoren-9-yl)phenyl)-2, 2'-bipydylamine (PFPhDPy) with bulky steric hindrance was synthesized successfully by substituting 9-(4-anilino)-9-phenyl-fluorene with 2-bromopyridine via Ullmann reaction, which is expected to possess good thermal stability, stable morphology, high triplet energy (ET), and good bipolar characteristics because of the bulky steric hindrance, excellent bipolar transporting characteristics of fluorene, interrupted conjugation, andelectrondeficient pyridine group. Thermo gravimetric analysis (TGA) indicates a decomposition transition temperature of 336℃ with 5% weight loss. Differential scanning calorimetry (DSC) curve reveals no crystallization and melting phenomena by heating to 190℃, which indicates the high morphological stability of the compound. The separation of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), calculated by density functional theory (DFT), indicates that a bipolar molecule was obtained and high triplet energy (ET, 3.0 eV) was calculated from the phosphorescence spectrum. The UV-Vis spectrum is independent of solvent effects with three absorption peaks at about 276, 298, and 308 nm, respectively. The fluorescence emission spectra show blue shift as the solvents' polarity increasing with emission peaks from 390 to 363 nm in the solvents of dichloromethane, ethyl acetate, ethanol, and acetonitrile. In addition, the structure of the compound was characterized by matrix-assisted laser desorption ionization time of flight mass spectrometer (MALDI-TOF MS), hydrogen nuclear magnetic resonance (1H NMR), and carbon nuclear magnetic resonance (13C NMR) spectra, respectively.

Key words: 9, 9-Diarylfluorene, Aniline, Steric, Friedel-Crafts reaction, Frontier molecular orbital