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2,5-PRODAN: synthesis and properties

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Abstract

The preparations of 1-(6-(dimethylamino)naphthalen-1-yl)propan-1-one (2,5-PRODAN, 2) and 7-(dimethylamino)-2,3-dihydrophenanthren-4(1H)-one 3 are described. The photophysical properties of these compounds are characterized and compared with those of PRODAN. Both compounds show solvatochromism that is similar in magnitude to PRODAN with a quantum yield that is nearly one order of magnitude smaller. Emission occurs from a locally excited (LE) state with charge-transfer character. There is no internal conversion to a different charge-transfer state as is seen in PRODAN.

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Notes and References

  1. G. Weber and F. J. Farris, Synthesis and spectral properties of a hydrophobic fluorescent probe: 6-propionyl-2-(dimethylamino) naphthalene, Biochemistry, 1979, 18, 3075–3078.

    Article  CAS  Google Scholar 

  2. R. K. Everett, H. A. A. Nguyen and C. J. Abelt, Does PRODAN Possess an O-TICT Excited State? Synthesis and Properties of Two Constrained Derivatives, J. Phys. Chem. A, 2010, 114, 4946–4950.

    Article  CAS  Google Scholar 

  3. B. N. Davis and C. J. Abelt, Synthesis and photophysical properties of models for twisted PRODAN and dimethylaminonaphthonitrile, J. Phys. Chem. A, 2005, 109, 1295–1298.

    Article  CAS  Google Scholar 

  4. B. C. Lobo and C. J. Abelt, Does PRODAN possess a planar or twisted charge-transfer excited state? Photophysical properties of two PRODAN derivatives, J. Phys. Chem. A, 2003, 107, 10938–10943.

    Article  CAS  Google Scholar 

  5. A. B. J. Parusel, W. Nowak, S. Grimme and G. Kohler, Comparative theoretical study on charge-transfer fluorescence probes: 6-propanoyl- 2-(N, N-dimethylamino) naphthalene and derivatives, J. Phys. Chem. A, 1998, 102, 7149–7156.

    Article  CAS  Google Scholar 

  6. A. B. J. Parusel, F. W. Schneider and G. Köhler, An ab initio study on excited and ground state properties of the organic fluorescence probe PRODAN, THEOCHEM, 1997, 398-399, 341–346.

    Article  Google Scholar 

  7. R. Everett, J. Hamilton and C. Abelt, Preparation of 5-Bromo-2- naphthol: The Use of a Sulfonic Acid as a Protecting and Activating Group, Molbank, 2009, 2009, M602.

    Article  Google Scholar 

  8. S. S. Silvonek, C. B. Giller and C. J. Abelt, Alternate syntheses of PRODAN and ACRYLODAN, Org. Prep. Proced. Int., 2005, 37, 589–594.

    Article  CAS  Google Scholar 

  9. J. Catalán, P. Perez, J. Laynez and F. G. Blanco, Analysis of the solvent effect on the photophysics properties of 6-propionyl-2-(dimethylamino) naphthalene (PRODAN), J. Fluoresc., 1991, 1, 215–223.

    Article  Google Scholar 

  10. A. Kawaki, Solvent-shift effect on electronic spectra and excited-state dipole moments, in Progress in Photochemistry and Photophysics, vol. 5, CRC, Boca Raton, FL, 1990, pp. 1–47.

    Google Scholar 

  11. A. Kawski, Ground-and excited-State dipole Moments of 6-propionyl- 2-(dimethylamino) naphthalene determined from solvatochromic shifts, Z Naturforsch, A: Phys. Sci., 1999, 54, 379–381.

    Article  CAS  Google Scholar 

  12. S. Murali and W. Rettig, TICT formation in para-and meta-derivatives of N-phenylpyrrole, J. Phys. Chem. A, 2006, 110, 28–37.

    Article  CAS  Google Scholar 

  13. B. A. Rowe, C. A. Roach, J. Lin, V. Asiago, O. Dmitrenko and S. L. Neal, Spectral Heterogeneity of PRODAN Fluorescence in Isotropic Solvents Revealed by Multivariate Photokinetic Analysis, J. Phys. Chem. A, 2008, 112, 13402–13412.

    Article  CAS  Google Scholar 

  14. V. Y. Artukhov, O. M. Zharkova and J. P. Morozova, Features of absorption and fluorescence spectra of prodan, Spectrochim. Acta, Part A, 2007, 68, 36–42.

    Article  Google Scholar 

  15. S. M. Bakalova and J. Kaneti, Solvent induced shifts of electronic spectra IV. Computational, study on PRODAN fluorescence and implications to the excited state structure, Spectrochim. Acta, Part A, 2009, 72, 36–40.

    Article  Google Scholar 

  16. B. Mennucci, M. Caricato, F. Ingrosso, C. Cappelli, R. Cammi, J. Tomasi, G. Scalmani and M. J. Frisch, How the Environment Controls Absorption and Fluorescence Spectra of PRODAN: A Quantum- Mechanical Study inHomogeneous and Heterogeneous Media, J. Phys. Chem. B, 2008, 112, 414–423.

    Article  CAS  Google Scholar 

  17. F. Moyano, M. A. Biasutti, J. J. Silber and N. M. Correa, New insights on the behavior of PRODAN in homogeneous media and in large unilamellar vesicles, J. Phys. Chem. B, 2006, 110, 11838–11846.

    Article  CAS  Google Scholar 

  18. N. Roesch and M. C. Zerner, Calculation of dispersion energy shifts in molecular electronic spectra, J. Phys. Chem., 1994, 98, 5817–5823.

    Article  CAS  Google Scholar 

  19. J. Catalán, Toward a Generalized Treatment of the Solvent Effect Based on Four Empirical Scales: Dipolarity (SdP, a New Scale), Polarizability (SP), Acidity (SA), and Basicity (SB) of the Medium, J. Phys. Chem. B, 2009, 113, 5951–5960.

    Article  Google Scholar 

  20. K. A. Zachariasse, Comment on pseudo-Jahn-Teller and TICT models: a photophysical comparison of meta-and para-DMABN derivatives [Chem. Phys. Lett. 305 (1999) 8]-The PICT model for dual fluorescence of aminobenzonitriles, Chem. Phys. Lett., 2000, 320, 8–13.

    Article  CAS  Google Scholar 

  21. K. A. Zachariasse, S. I. Druzhinin, W. Bosch and R. Machinek, Intramolecular charge transfer with the planarized 4-aminobenzonitrile 1-tert-butyl-6-cyano-1, 2, 3, 4-tetrahydroquinoline (NTC6), J. Am. Chem. Soc., 2004, 126, 1705–1715.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, College of William and Mary, Williamsburg, Virginia, USA

    Christopher J. Abelt, Tao Sun & Renata K. Everett

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  1. Christopher J. Abelt
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  2. Tao Sun
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  3. Renata K. Everett
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Correspondence to Christopher J. Abelt.

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Abelt, C.J., Sun, T. & Everett, R.K. 2,5-PRODAN: synthesis and properties. Photochem Photobiol Sci 10, 618–622 (2011). https://doi.org/10.1039/c0pp00377h

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  • DOI: https://doi.org/10.1039/c0pp00377h

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