Abstract
This review presents research that centers on verification of a new photophysical model for the excited state properties of N-phenyl-1,8-naphthalimides. The first section of the review highlights the critical advantages that two-color dyes possess relative to single color dyes with respect to internal calibration and quantitative analysis. Recent examples are provided to show the development of the modified photophysical model and the fluorescence properties on which this model is based upon. Results shown in this section serve as a guide or roadmap toward future strategies, specifically, which substituents are required for the promotion of dual fluorescence (DF). Based on these concepts, a 3×3 matrix of substituted N-aryl-1,8-naphthalimides was synthesized for the evaluation and discovery of DF. The matrix elements included for this study were based on a predictive model that we propose as a seesaw balanced photophysical model. This model serves as guide to optimize the dual fluorescence emission from N-phenyl-1,8-naphthalimdes by appropriate placement of substituent groups at both the 4-position of the N-arene as well as the 4ʹ-position of the naphthalene ring. Steady-state fluorescence studies under a variety of solvents indicate that four of the nine dyes in the matrix are dual fluorescent. Given the difficulties in predicting excited state properties such as molecular fluorescence, this ratio of four out of nine “hits’ for discovering DF signifies proof of principle for this proposed model and should provide a rational basis for the synthesis of future DF 1,8-naphthalimide systems.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Notes
- 1.
Similar to [15], we observed absorption maxima at 340, 353 and 369 nm, however excitation at these wavelengths did not promote LW emission.
- 2.
Both compounds 10 and 13 have emission bands at 431 and 424 nm, respectively which are considered to be the LW emission relative to the SW emission which occurs respectively at 373 and 377 nm.
References
J.R. Lakowicz, Probe design in chemical sensing; Plenum Press: New York, 1999.
B. Valeur, Molecular fluorescence; Wiley VCH: Weinheim, 2002.
Y. Dharmadi, R DNA microarrays: Experimental issues, data analysis, and application to bacterial systems. Biotechnol. Prog., 20, 1309–1324 (2004).
C.B. Epstein, R.A. Butow, Microarray technology – enhanced versatility, persistent challenge. Curr. Opin. Biotechnol., 314, 1–26 (2000).
W.C. Tse, D.L. Boger, A fluorescent intercalator displacement assay for establishing DNA binding selectivity and affinity. Acc. Chem. Res., 37, 61–69 (2004).
D.M. Benson, J. Bryan, A.L. Plant, A.M. Gotto, L.C. Smith, Digital imaging fluorescence microscopy – spatial heterogeneity of photobleaching rate constants in individual cells. J. Cell Biol., 100, 1309–1323 (1985).
A.P. Demchenko, The problem of self-calibration of fluorescence signal in microscale sensor systems, Lab Chip, 5, 1210–1223 (2005).
A.P. Demchenko, Optimization of fluorescence response in the design of molecular biosensors. Anal. Biochem., 343, 1–22 (2005).
A. Demeter, T. Berces, L. Biczok, V. Wintgens, P. Valat, J. Kossanyi, Spectroscopic properties of aromatic dicarboximies. 2. Substituent effect on the photophysical properties of N-phenyl-1,2-Naphthalimide. J. Chem. Soc. Faraday Trans., 90, 2635–2641 (1994).
A. Demeter, T. Berces, L. Biczok, V. Wintgens, P. Valat, J. Kossanyi, Comprehensive model of the photophysics of N-phenylnaphthalimides: The role of solvent and rotational relaxation. J. Phys. Chem., 100, 2001–2011 (1996).
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, 4763–4771 (2002).
S.V Shevyakov, H. Li, R. Muthyala, A.E. Asato, J.C. Croney, D.M. Jameson, R.S.H. Liu, Orbital control of the color and excited state properties of formylated and fluorinated derivatives of azulene. J. Phys. Chem. A, 107, 3295–3299 (2003).
H. Cao, T. McGill, M.D. Heagy, Substituent effects on monoboronic acid sensors for saccharides based on N-phenyl-1,8-naphthalenedicarboximides. J. Org. Chem., 69, 2959–2966 (2004).
H. Cao, D.I. Diaz, N. DiCesare, J.R. Lakowicz, M.D. Heagy, Monoboronic acid sensor that displays anomalous fluorescence sensitivity to glucose. Org. Lett., 4, 1503–1505 (2002).
V. Wintgens, P. Valat, J. Kossanyi, A. Demeter, L. Biczok, T. Berces, Spectroscopic properties of aromatic dicarboximides. Part 3: Substituent effect on the photophysical properties of N-phenyl-2,3-naphthalimides. J. Photochem. Photobiol. A Chem., 93, 109–117 (1996).
A. Demeter, T. Berces, L. Biczok, V. Wintgens, P. Valat, J. Kossanyi, Spectroscopic properties of aromatic dicarboximides. Part 4. On the modification of the fluorescence and intersystem crossing processes of molecules by electron-donating methoxy groups at different positions. The case of 1,8-naphthalimides. New J. Chem., 20, 1149–1158 (1996).
I.D. Albert, T.J. Marks, M.A. Ratner, Large molecular hyperpolarizabilities. Quantitative analysis of aromaticity and auxiliary donor-acceptor effects. J. Am. Chem. Soc., 119, 6575–6582 (1997).
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2010 Springer Science+Business Media, LLC
About this chapter
Cite this chapter
Begaye, M.P., Nandhikonda, P., Cao, Z., Heagy, M.D. (2010). New Dual Fluorescent Dyes Based on Modified “Excited State with Extended Conjunction” Photophysical Model. In: Geddes, C.D. (eds) Reviews in Fluorescence 2008. Reviews in Fluorescence 2008, vol 2008. Springer, New York, NY. https://doi.org/10.1007/978-1-4419-1260-2_19
Download citation
DOI: https://doi.org/10.1007/978-1-4419-1260-2_19
Publisher Name: Springer, New York, NY
Print ISBN: 978-1-4419-0828-5
Online ISBN: 978-1-4419-1260-2
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)