Citation: SHEN Jian-Lei, YANG Xin-Guo, HUANG Liao, SHEN Qi-Li, LIU Zhen-Hui, ZHANG Feng-Ju. Synthesis and Photophysical Behavior of Two Novel Bis(1,8-naphthalimides) Containing Triazine Spacers[J]. Acta Physico-Chimica Sinica, ;2012, 28(08): 1992-1999. doi: 10.3866/PKU.WHXB201205282 shu

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

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 Date: 29 March 2012
Available Online: 28 May 2012
Fund Project: 国家自然科学基金(50573019) (50573019) 浙江大学硅材料国家重点实验室开放课题(SKL2009-5) (SKL2009-5)

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.
- 1,8-naphthalimide,
- Cyanuric chloride,
- Excimer,
- Exciplex,
- Hydrogen bond
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