Citation: Zhi-Yong Wu, Jing-Nan Cui, Xu-Hong Qian, Tian-Yu Liu. A 4-aminonaphthalimide based environmentally sensitive fluorescence probe[J]. Chinese Chemical Letters, ;2013, 24(05): 359-361. shu

A 4-aminonaphthalimide based environmentally sensitive fluorescence probe

1.
a State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012, China;
2.
b Shanghai Key Laboratory of Chemical Biology, East China University of Science and Technology, Shanghai 200237, China

Corresponding author: Jing-Nan Cui, Xu-Hong Qian,
Received Date: 4 February 2013
Available Online: 11 March 2013

A simply synthesized 4-aminonaphthalimide derivative 1 expresses both polarity and viscosity sensitive fluorescence spectra, indicating its potential usage as an environmentally sensitive fluorescence probe. By comparing the fluorescence behavior of 1 with that of a known 4-aminonaphthalimide derivative 2, it was found that the substitution of the 4-amino group has profound influence on the environmentally sensitive fluorescence properties of 4-aminonaphthalimide.
- 4-Aminonaphthalimide,
- Environmentally sensitive,
- Fluorescence probe,
- Substitution effects
1. [1]
  [1] R.W. Sinkeldam, N.J. Greco, Y. Tor, Fluorescent analogs of biomolecular building blocks: design, properties, and applications, Chem. Rev. 110 (2010) 2579-2619.
2. [2]
  [2] R.N. Dsouza, U. Pischel, W.M. Nau, Fluorescent dyes and their supramolecular host/guest complexes with macrocycles in aqueous solution, Chem. Rev. 111 (2011) 7941-7980.
3. [3]
  [3] M.A. Haidekker, E.A. Theodorakis, Molecular rotors-fluorescent biosensors for viscosity and flow, Org. Biomol. Chem. 5 (2007) 1669-1678.
4. [4]
  [4] M.S. Alexiou, V. Tychopoulos, S. Ghorbanian, et al., The UV-visible absorption and fluorescence of some substituted 1,8-naphthalimides and naphthalic anhydrides, J. Chem. Soc. Perkin Trans. 2 (1990) 837-842.
5. [5]
  [5] S. Saha, A. Samanta, Influence of the structure of the amino group and polarity of the medium on the photophysical behavior of 4-amino-1,8-naphthalimide derivatives, J. Phys. Chem. A 106 (2002) 4763-4771.
6. [6]
  [6] G.R. Bardajee, A.Y. Li, J.C. Haley, M.A. Winnik, The synthesis and spectroscopic properties of novel, functional fluorescent naphthalimide dyes, Dyes Pigm. 79 (2008) 24-32.
7. [7]
  [7] D. Yuan, R.G. Brown, J.D. Hepworth, et al., The synthesis and fluorescence of novel N-substituted-1,8-naphthylimides, J. Heterocycl. Chem. 45 (2008) 397-404.
8. [8]
  [8] G. Saroja, A. Samanta, Polarity of the micelle-water interface as seen by 4-aminophthalimide, a solvent sensitive fluorescence probe, Chem. Phys. Lett. 246 (1995) 506-512.
9. [9]
  [9] G. Loving, B. Imperiali, A versatile amino acid analogue of the solvatochromic fluorophore 4-N,N-dimethylamino-1,8-naphthalimide: a powerful tool for the study of dynamic protein interactions, J. Am. Chem. Soc. 130 (2008) 13630-13638.
10. [10]
  [10] Z. Li, Q. Yang, R. Chang, et al., N-Heteroaryl-1,8-naphthalimide fluorescent sensor for water: molecular design, synthesis and properties, Dyes Pigm. 88 (2011) 307-314.
11. [11]
  [11] J.N. Demas, G.A. Crosby, The measurement of photoluminescence quantum yields. A review, J. Phys. Chem. 75 (1971) 991-1024.
12. [12]
  [12] J.A. Dean, Lange's Handbook of Chemistry, 15th ed., McGraw-Hill, New York, 19995090-5129.
13. [13]
  [13] C. Reichardt, Solvatochromic dyes as solvent polarity indicators, Chem. Rev. 94 (1994) 2319-2358.
14. [14]
  [14] Z.R. Grabowski, K. Rotkiewicz, W. Rettig, Structural changes accompanying intramolecular electron transfer: focus on twisted intramolecular charge-transfer states and structures, Chem. Rev. 103 (2003) 3899-4032.
15. [15]
  [15] T. Förster, G. Hoffmann, Die Viskositätsabhngigkeit der Fluoreszenzquantenausbeuten einiger Farbstoffsysteme,(Effect of viscosity on the fluorescence quantum yield of some dye systems), Z. Phys. Chem. 75 (1971) 63-76.
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1.
沈阳化工大学材料科学与工程学院沈阳 110142