Acta Phys. -Chim. Sin. ›› 2012, Vol. 28 ›› Issue (08): 1992-1999.doi: 10.3866/PKU.WHXB201205282

• PHOTOCHEMISTRY AND RADIATION CHEMISTRY • Previous Articles     Next Articles

Synthesis and Photophysical Behavior of Two Novel Bis(1,8-naphthalimides) Containing Triazine Spacers

SHEN Jian-Lei1, YANG Xin-Guo1,2, HUANG Liao1, SHEN Qi-Li1, LIU Zhen-Hui1, ZHANG Feng-Ju1   

  1. 1. Department of Polymer Materials, College of Materials Science & Engineering, Hunan University, Changsha 410082, P. R. China;
    2. State Key Laboratory of Silicon Materials, Zhejiang University, Hangzhou 310027, P. R. China
  • Received:2012-03-29 Revised:2012-05-28 Published:2012-07-10
  • Contact: YANG Xin-Guo
  • Supported by:

    The project was supported by the National Natural Science Foundation of China (50573019), Open Research Program of State Key Laboratory of Silicon Materials, Zhejiang University, China (SKL2009-5), and Open Foundation for Large Precision Instruments of Hunan University.


Two novel bis(1,8-naphthalimides) (3 and 5) containing triazine spacers have been synthesized from 1,8-naphthalic anhydride and cyanuric chloride. The photophysical properties of 3 and 5 have been investigated by UV-Vis absorption and fluorescence spectroscopy. As with N-butyl-1, 8-naphthalimide in polar dichloromethane, chloroform or methanol, the fluorescence spectra of 3 and 5 exhibit a short-wavelength emission band (λ<400 nm) typically observed for 1,8-naphthalimide derivatives, and a broad and red-shifted intramolecular excimer emission band (λ>450 nm). In addition, owing to the specific conformational isomerism, the emission intensity of 3 is significantly quenched by intramolecular electron transfer. In the apolar solvent methyl cyclohexane, the strong hydrogen-bonding interactions between triazine linkers drive monomeric 5 aggregation that is responsible for intermolecular excimer emission. In toluene, both 3 and 5 do not display strong excimer emission. Instead, exciplex formation of toluene with naphthalimide moieties in 3 or 5 is observed. Finally, the excited-state properties of solid films of 3 and 5 have excimer emission around 465 and 469 nm, respectively.

Key words: 1,8-naphthalimide, Cyanuric chloride, Excimer, Exciplex, Hydrogen bond