Theme and Variation on N-Aryl-1, 8-Napthalimides: Minimal Modification to Red-Shifted Fluorescence and Applications in Fluorescent Chemosensors

  • Premchendar Nandhikonda
  • Zhi Cao
  • Michael D. Heagy
Chapter
Part of the Reviews in Fluorescence book series (RFLU, volume 2009)

Abstract

Our continuing efforts into the development of N-aryl-1,8-naphthalic dicarboximides (NI) as dual fluorescent (DF) dyes for biomedical applications has led to new insights into the photophysical features that these simple dyes can be designed to display. Consequently, the development of new DF dyes with improved fluorescent properties represents a major focus of our research. The first section of this review presents results involving a “minimal modification approach” to red-shifted absorption and fluorescence in NIs and affords some key design concepts for improved DF dyes. In this section, we demonstrate the significant effect of appropriately placed charges can have on the emission properties of these unique dyes. In the next section, dual fluorescent probes for the ions of potassium and sodium are introduced with the NI framework and crown ether receptors. The ratiometric features of these dyes from absorption as well as fluorescence spectroscopy are highlighted. Finally, in the third section, we demonstrate dual fluorescence detection of saccharides with the same DF dye component as our ion probe, in this case, however, a simple phenylboronic acid is utilized as a saccharide binding component.

Keywords

Saccharide Pyridine Fluor Anhydride Naphthalene 

References

  1. 1.
    Durrant JR, Haque SA, Palomares E (2006) Photochemical energy conversion: from molecular dyads to solar cells. Chem Commun 37(51):3279–3289CrossRefGoogle Scholar
  2. 2.
    Dyakonov V, Sariciftci NS (2003) Organic photovoltaics: concepts and realization, vol 60. Springer, New YorkGoogle Scholar
  3. 3.
    Valeur B (2001) Molecular fluorescence: principles and applications. Wiley, New YorkCrossRefGoogle Scholar
  4. 4.
    Klymchenko AS, Demchenko AP (2002) Electrochromic modulation of excited-state intramolecular proton transfer: the new principle in design of fluorescence sensors. J Am Chem Soc 124:12372–12379PubMedCrossRefGoogle Scholar
  5. 5.
    Klymchenko AS, Ozturk T, Demchenko AP (2002) Synthesis of furanochromones: a new step in improvement of fluorescence properties. Tetrahedron Lett 43:7079–7082CrossRefGoogle Scholar
  6. 6.
    Abad S, Kluciar M, Miranda MA, Pischel U (2005) Proton-induced fluorescence switching in novel naphthalimide-dansylamide dyads. J Org Chem 70:10565–10568PubMedCrossRefGoogle Scholar
  7. 7.
    Badugu R (2005) Fluorescence sensor design for transition metal ions: the role of the PIET interaction efficiency. J Fluoresc 15:71–83PubMedCrossRefGoogle Scholar
  8. 8.
    Cho DW, Fujitsuka M, Choi KH, Park MJ, Yoon UC, Majima TJ (2006) Photoinduced electron transfer processes in 1,8-naphthalimide-linker-phenothiazine dyads. J Phys Chem B 110:4576–4582PubMedCrossRefGoogle Scholar
  9. 9.
    Koner AL, Schatz J, Nau WM, Pischel U (2007) Selective sensing of citrate by a supramolecular 1,8-naphthalimide/calix[4]arene assembly via complexation-modulated pK(a) shifts in a ternary complex. J Org Chem 72:3889–3895PubMedCrossRefGoogle Scholar
  10. 10.
    Miskolczy Z, Nyitrai J, Biczók L, Sebok-Nagy K, Körtvélyesi T (2006) Photophysical properties of novel cationic naphthalimides. J Photochem Photobiol A Chem 182:99–106CrossRefGoogle Scholar
  11. 11.
    Takahashi S, Nozaki K, Kozaki M, Suzuki S, Keyaki K, Ichimura A, Matsushita T, Okada K (2008) Photoinduced electron transfer of N-[(3-and 4-diarylamino)phenyl]-1,8-naphthalimide dyads: orbital-orthogonal approach in a short-linked D-A system. J Phys Chem A 112:2533–2542PubMedCrossRefGoogle Scholar
  12. 12.
    Frisch MJ et al (2004) Gaussian 03. Gaussian, Wallingford, CTGoogle Scholar
  13. 13.
    Saha S, Samanta A (2002) 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 106:4763–4771CrossRefGoogle Scholar
  14. 14.
    Fromherz P (1995) Monopole dipole model for symmetrical solvatochromism of hemicyanine dyes. J Phys Chem 99:7188–7192CrossRefGoogle Scholar
  15. 15.
    Demeter A, Berces T, Biczok L, Wintgens V, Valat P, Kossanyi J (1996) Comprehensive model of the photophysics of N-phenylnaphthalimides: the role of solvent and rotational relaxation. J Phys Chem 100:2001–2011CrossRefGoogle Scholar
  16. 16.
    Minta A, Tsien RY (1989) Fluorescent indicators for cystolic sodium. J Biol Chem 264:19449–19457PubMedGoogle Scholar
  17. 17.
    Tsien RY (1989) Fluorescent indicators of ion concentrations. Meth Cell Biol 30:127–156CrossRefGoogle Scholar
  18. 18.
    Lakowicz RJ (2006) Principles of fluorescence spectroscopy, 3rd edn. Springer, New York, pp 634–644CrossRefGoogle Scholar
  19. 19.
    Szmacinski H, Lakowicz RJ (1999) Potassium and sodium measurements at clinical concentrations using phase-modulation fluorometry. Sens Actuators B Chem 60:8–18CrossRefGoogle Scholar
  20. 20.
    Liu HL, Zhang H, Li FA, Xie WJ, Jiang BY (2006) Intramolecular charge transfer dual fluorescent sensors from 4-(dialkylamino)benzanilides with metal binding site within electron acceptor. Tetrahedron 62:10441–10449CrossRefGoogle Scholar
  21. 21.
    Malval PJ, Lapouyade R (2001) Derivatization of 4-(dimethylamino)benzamide to dual fluorescent ionophores: divergent spectroscopic effects dependent on N or O amide chelation. Helv Chem Acta 84:2439CrossRefGoogle Scholar
  22. 22.
    Crossley R, Goolamali Z, Sammes PG (1994) Synthesis and properties of a potential extracellular fluorescent-probe for potassium. J Chem Soc Perkin Trans 2:1615–1623Google Scholar
  23. 23.
    Kaneda T, Sugihara K, Kamiya H, Misumi S (1981) Synthetic macrocyclic ligands. 4. Lithium ion-characteristic coloration of a crowned dinitrophenylazophenol. Tetrahedron Lett 22:4407CrossRefGoogle Scholar
  24. 24.
    de Silva AP, Eilers J, Zlokarnik G (1999) Emerging fluorescence sensing technologies: from photophysical principles to cellular applications. Proc Natl Acad Sci USA 96:8336PubMedCrossRefGoogle Scholar
  25. 25.
    Shinkai S, Takeuchi M, Ikeda A (2000) Molecular machines useful for the design of chemosensors. In: Osada Y, De Rossi DE (eds) Polymer sensors and actuators. Springer, Berlin, pp 183–206Google Scholar
  26. 26.
    He H, Mortellaro AM, Leiner PJM, Young TS, Fraatz JR, Tusa K (2003) A fluorescent chemosensor for sodium based on photoinduced electron transfer. J Anal Chem 75:549–555CrossRefGoogle Scholar
  27. 27.
    Cosnard F, Wintgens V (1998) A new fluoroionophore derived from 4-amino-N-methyl-1,8-naphthalimide. Tetrahedron Lett 39:2751–2754CrossRefGoogle Scholar
  28. 28.
    Cao H, Chang V, Hernandez R, Heagy MD (2005) Matrix screening of substituted N-aryl-1,8-naphthalimides reveals new dual fluorescent dyes and unusually bright pyridine derivatives. J Org Chem 70:4929–4934PubMedCrossRefGoogle Scholar
  29. 29.
    Demchenko PA (2005) The problem of self-calibration of fluorescence signal in microscale sensor systems. Lab Chip 5:1210–1223PubMedCrossRefGoogle Scholar
  30. 30.
    Cao H, McGill T, Heagy DM (2004) Substituent effects on monoboronic acid sensors for saccharides based on N-phenyl-1,8-naphthalenedicarboximides. J Org Chem 69:2959–2966PubMedCrossRefGoogle Scholar
  31. 31.
    James TD, Shinkai S (2002) Artificial receptors as chemosensors for carbohydrates. Top Curr Chem 218:159–200CrossRefGoogle Scholar
  32. 32.
    Fang H, Kaur G, Wang B (2004) Progress in boronic acid-based fluorescent glucose sensors. J Fluoresc 14:481–489PubMedCrossRefGoogle Scholar
  33. 33.
    Finney SJ, Zekveld C, Elia A, Evans TW (2003) Glucose control and mortality in critically ill patients. J Am Med Assoc 290:2041–2047CrossRefGoogle Scholar
  34. 34.
    Wentholt IM, Vollebregt MA, Hart AA, Hoekstra JB, DcVrics JH (2005) Comparison of a needle-type and a microdialysis continuous glucose monitor in type 1 diabetic patients. Diabetes Care 28:2871–2876PubMedCrossRefGoogle Scholar
  35. 35.
    Pickup JC, Hussain F, Evans ND, Rolinski OJ, Birch DJS (2005) Fluorescence-based glucose sensors. Biosens Bioelectron 20:2555–2565PubMedCrossRefGoogle Scholar
  36. 36.
    James TD, Sandanayake KRAS, Shinkai S (1995) Chiral discrimination of monosaccharides using a fluorescent molecular sensor. Nature 374:345–357CrossRefGoogle Scholar
  37. 37.
    Wang W, Gao X, Wang B (2002) Boronic acid-based sensors. Curr Org Chem 6:1285–1317CrossRefGoogle Scholar
  38. 38.
    Striegler S (2003) Selective carbohydrate recognition by synthetic receptors in aqueous solution. Curr Org Chem 7:81–102CrossRefGoogle Scholar
  39. 39.
    Yan J, Fang H, Wang B (2005) Boronolectins and fluorescent boronolectins: an examination of the detailed chemistry issues important for the design. Med Res Rev 25:490–520PubMedCrossRefGoogle Scholar
  40. 40.
    Heller A (1999) Implanted electrochemical glucose sensors for the management of diabetes. Annu Rev Biomed Eng 1:153–175PubMedCrossRefGoogle Scholar
  41. 41.
    Yoon JY, Czarnik AW (1992) Fluorescent chemosensors of carbohydrates – a means of chemically communicating the binding of polyols in water based on chelation enhanced quenching. J Am Chem Soc 114:5874–5875CrossRefGoogle Scholar
  42. 42.
    Mader HS, Wolfbeis OS (2008) Boronic acid based probes for microdetermination of saccharides and glycosylated biomolecules. Microchim Acta 162:1–34CrossRefGoogle Scholar
  43. 43.
    Yamamoto H, Ori A, Ueda K, Dusemund C, Shinkai S (1996) Visual sensing of fluoride ion and saccharides utilizing a coupled redox reaction of ferrocenylboronic acids and dye molecules. Chem Commun 407–408.Google Scholar
  44. 44.
    Shinmori H, Takeuchi M, Shinkai S (1995) Spectroscopic sugar sensing by a stilbene derivative ith push-pull ((OH)(2)B) – type substituents. Tetrahedron 51:1893–1902CrossRefGoogle Scholar
  45. 45.
    Gabai R, Sallacan N, Chegel V, Bourenko T, Katz E, Willner I (2001) Characterization of the swelling of acrylamidophenylboronic acid-acrylamide hydrogels upon interaction with glucose by faradaic impedance spectroscopy, chronopotentiometry, quartz-crystal microbalance (QCM), and surface plasmon resonance (SPR) experiments. J Phys Chem B 105:8196–8202CrossRefGoogle Scholar
  46. 46.
    Shoji E, Freund MS (2002) Potentiometric saccharide detection based on the pKa changes of poly(aniline boronic acid). J Am Chem Soc 124:12486–12493PubMedCrossRefGoogle Scholar
  47. 47.
    James TD, Linnane P, Shinkai S (1996) Fluorescent saccharide receptors: a sweet solution to the design, assembly and evaluation of boronic acid derived PET sensors. Chem Commun 281–288.Google Scholar
  48. 48.
    DiCesare N, Pinto MR, Schanze KS, Lakowicz JR (2002) Saccharide detection based on the amplified fluorescence quenching of a water-soluble poly(phenylene ethynylene) by a boronic acid functionalized benzyl viologen derivative. Langmuir 18:7785–7787CrossRefGoogle Scholar
  49. 49.
    Murakami H, Nagasaki T, Hamachi I, Shinkai S (1993) Sugar sensing utilizing aggregation properties of a boronic acid appended porphyrin. Tetrahedron Lett 34:6273–6276CrossRefGoogle Scholar
  50. 50.
    Coskun A, Akkaya EU (2004) Three-point recognition and selective fluorescence sensing of L-DOPA. Org Lett 6:3107–3109PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Premchendar Nandhikonda
    • 1
  • Zhi Cao
    • 1
  • Michael D. Heagy
    • 1
  1. 1.Department of ChemistryNew Mexico Institute of Mining and TechnologySocorroUSA

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