[1] Jiang Wei, Tang Jinan, Sun Yueming, Xu Wenlian, et al. Synthesis and photochemical properties of two ICT compoundswith naphthalimide and diarylamine units [J]. Journal of Southeast University (English Edition), 2008, 24 (2): 243-246. [doi:10.3969/j.issn.1003-7985.2008.02.024]

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Synthesis and photochemical properties of two ICT compoundswith naphthalimide and diarylamine units()

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Journal of Southeast University (English Edition)[ISSN:1003-7985/CN:32-1325/N]

Volumn:

24

Issue:

2008 2

Page:

243-246

Research Field:

Chemistry and Chemical Engineering

Publishing date:

2008-06-03

Info

Title:

Synthesis and photochemical properties of two ICT compoundswith naphthalimide and diarylamine units

Author(s):

Jiang Wei;  Tang Jinan;  Sun Yueming;  Xu Wenlian;  Wang Hualin

School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, China

Keywords:

naphthalimide;  diarylamine;  photoluminescence;  UV-vis spectrum;  intramolecular charge transfer

PACS:

O625

DOI:

10.3969/j.issn.1003-7985.2008.02.024

Abstract:

Two new diarylamine-substituted 1, 8-naphthalimide derivatives are synthesized by CuⅠ/18-crown-6/K₂CO₃ catalyst system and characterized by Fourier transform infrared(FT-IR), ¹H-NMR and elemental analyses.The UV-vis absorption and photoluminescent(PL)spectra of the systems in n-hexane, tetrahydrofuran(THF), and CH₂Cl₂ are investigated.These naphthalimide molecules have an absorption band centered at about 450 nm, which is assigned to an intramolecular charge-transfer(ICT)transition, and they emit light at 492, 501 nm in a nonpolar solvent such as n-hexane, and at 600, 620 nm in a polar solvent such as CH₂Cl₂.From the Lippert-Mataga equation, the difference of the dipole moment between the excited state and the ground state is estimated to be 9.2 and 9.8 D for 4-(diphenylamine)-N-(2-methoxyphenyl)-1, 8-naphthalimide(DMN-1)and 4-(2-naphthylphenylamine)-N-(2-methoxyphenyl)-1, 8-naphthalimide(DMN-2), respectively.This large change in the dipole moment upon excitation is typical for photoinduced ICT processes.

References:

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Memo

Memo:

Biographies: Jiang Wei(1980—), male, graduate;Sun Yueming(corresponding author), male, doctor, professor, sun@seu.edu.cn.
Foundation items: The Ph.D.Programs Foundation of Ministry of Education of China(No.20030286012), the High Technology Research and Development Program of Jiangsu Province(No.BG2005034).
Citation: Jiang Wei, Tang Jinan, Sun Yueming, et al.Synthesis and photochemical properties of two ICT compounds with naphthalimide and diarylamine units[J].Journal of Southeast University(English Edition), 2008, 24(2):243-246.

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