Journals / Turkish Journal of Chemistry / 2004 / Cilt: 28 - Sayı: 4

Photophysical properties and electrochemistry of the N,N'-bis-n-butyl derivative of naphthalene diimide

Pages
415–424
Publication Date
2022-11-04
DOI
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⚡ TL;DR(Too Long; Didn't Read)

It has been found that, in contrast to perylene diimide derivatives, which form $Pi$-electron donor-acceptor complexes with aromatic donor molecules of naphthalene, phenanthrene, pyrene and perylene, BBND does not form $Pi$-electron-donor acceptor complexes with aromatic donor molecules.

📌 3 Key Takeaways

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Objective & Hypothesis:The spectral-luminescent properties and electrochemistry of the N,N'-bis-n-butyl derivative of naphthalene diimide were studied.
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Key Findings & Data:The main photophysical parameters (quantum yield, rate constants of fluorescence and of non-radiative deactivation and fluorescence lifetime) were determined.
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Conclusion & Impact:It has been found that, in contrast to perylene diimide derivatives, which form $Pi$-electron donor-acceptor complexes with aromatic donor molecules of naphthalene, phenanthrene, pyrene and perylene, BBND does not form $Pi$-electron-donor acceptor complexes with aromatic donor molecules.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

Abstract

The spectral-luminescent properties and electrochemistry of the N,N'-bis-n-butyl derivative of naphthalene diimide were studied. The main photophysical parameters (quantum yield, rate constants of fluorescence and of non-radiative deactivation and fluorescence lifetime) were determined. The LUMO value (-3.51 eV) was determined by cyclic voltammetry. The N,N'-bis-n-butyl derivative of naphthalene diimide (BBND) shows 2 reversible reduction steps (-1.19 V and -1.75 V vs. Ferrocene) in chloroform. Quenching the fluorescence emissions of aromatic donor molecules in acetonitrile revealed the electron acceptor ability of the studied naphthalene diimide derivative. It has been found that, in contrast to perylene diimide derivatives, which form $Pi$-electron donor-acceptor complexes with aromatic donor molecules of naphthalene, phenanthrene, pyrene and perylene, BBND does not form $Pi$-electron-donor acceptor complexes with aromatic donor molecules.

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Cite This Article

DİLGİN, Y., ALP, S., İÇLİ, S., KÖZ, B., POSOKHOV, Y. (2022). Photophysical properties and electrochemistry of the N,N'-bis-n-butyl derivative of naphthalene diimide. Turkish Journal of Chemistry, Cilt: 28 - Sayı: 4, 415–424. https://ajindex.com/articles/602239

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References (21)

  1. A. Viehbeck, M.J. Goldberg and C.A. Kovac, J. Electrochem. Soc. 137, 1460 (1990)
  2. C.J. Zhong, W.S.V. Kwan and L.L. Miller, Chem. Mater. 4, 1423 (1992)
  3. V.L. Cammarata, L.L. Atanasoska, C.J. Miller, B. Kolaskie and B. Stallman, Langmuir 8, 876 (1992)
  4. G. Heywang, L. Born, H.G. Fitzky, T. Hassel, J. Hocker, H.K. Muller, B. Pittel and S. Roth, Angew. Chem.Int. Ed. Engl. 28, 483 (1989)
  5. L.L. Miller, C.J. Zhong and P. Kasai, J. Am. Chem. Soc. 115, 5982 (1993)
  6. J.F. Penneau, B.J. Stallman, P.H. Kasai and L.L. Miller, Chem. Mater. 3 791 (1991)
  7. N. Kimizuka, T. Kawasaki, K. Hirata and T. Kunitake, J. Am. Chem. Soc. 117, 6360 (1995). 8.K. Hasharoni, H. Levanon, S.R. Greenfield, D.J. Gosztola, W.A. Svec and M.R. Wasielewski, J. Am. Chem.Soc. 117, 8055 (1995)
  8. T.C. Barros, S. Brochsztain, V.G. Toscano, P.B. Filho and M.J. Politi, J. Photochem. Photobiol. A: Chem.111, 97 (1997)
  9. D. Meissner and J. Rostalski, Syn. Met. 121, 1551 (2001). 11. a) S. Alp, S. Erten, C. Karapire, B. Koz, A.O. Doroshenko and S. Icli, J. of Photochem. Photobiol. A:Chem. 135, 103 (2000). b) H. Icil and S. Icli, J. Polym. Sci. A: Polym. Chem. 35, 2137 (1997)
  10. W.H. Melhuish, J. Phys. Chem. 65, 229 (1961)
  11. S.R. Meech and D. Phillps, J. Photochem. 23, 193 (1983)
  12. S.I. Kotelevskiy, J. Luminescence. 79, 211 (1998)
  13. J.R. Lakowicz, "Principles of fluorescence spectroscopy", part 8, New York, Kluwer Academic/Plenum Publisher, 1999
  14. F. Scholz and B. Meyer, "Electroanalytical Chemistry. A Series of Advances", Vol. 20, Eds. A.J. Bard,I. Rubinstein, Marcel Soc., 105: 6555, 1983
  15. T.C. Barros, G.R. Molinari, P.B. Filho, V.G. Toscano and M.J. Politi, J. Photochem. Photobiol. A: Chem.76, 55 (1993)
  16. N.J. Turro, "Molecular Photochemistry", London, Benjamin Pub., 1965
  17. S. Green and A. Fox, J. Phys. Chem. 99, 14752 (1999)
  18. V. Wintgens, P. Valat, J. Kossanyi, L. Biczok, A. Demeter and T. Berces, J. Chem. Soc., Faraday Trans.90, 411 (1994)
  19. H.M. Koepp, H. Wendt and H. Strehlow, Z. Electrochem. 64, 483 (1960)
  20. J.L. Bredas, R. Silbey, D.S. Bourdreaux and R.R. Chance, J. Am. Chem. Soc. 105, 6555 (1983). 23. a) D. Uzun, M.E.Özser, K. Yüney, H. Icil and M. Demuth, J. Photochem. Photobiol. A: Chem. 156, 45 (2003). b) M.E. Ozser, D. Uzun, I. Elci, H. Icil and M. Demuth, Photochem. Photobiol Sci., 2, 218 (2003). c) B. Ramachandram, N.B. Sankaran, R. Kankar, S. Saha and A. Samant, Tetrahedron, 56, 7041 (2000)
  21. S. Icli, S. Demic, B. Dindar, A.O. Dorosh