Abstract
The photophysical properties of the new pyridin-2′-yl-1,2,3-triazolechromophore have been investigated. Spectroscopic experiments and molecular modelling have provided evidence for a photoinduced charge transfer occurring from the triazolegroup to the pyridine ring. Hepta- and tetrachromophoric systems have been synthesized by covalently linking seven or four chromophores of this kind, respectively, to a β-cyclodextrin and a calix[4]arene. They exhibit different fluorescence spectra, decays and quantum yields. Special attention has been paid to the binding of cadmium and zinc ions and to the resulting photophysical effects which are various and very different for the grafted β-cyclodextrin and calix[4]arene systems.
Similar content being viewed by others
Notes and references
M. N. Berberan-Santos, J. Canceill, J. C. Brochon, L. Jullien, J. M. Lehn, J. Pouget, P. Tauc and B. Valeur, Multichromophoric cyclodextrins. 1. Synthesis of o-naphthoyl-β-cyclodextrins and investigation of excimer formation and energy hopping, J. Am. Chem. Soc., 1992, 114, 6427–6436
M. N. Berberan-Santos, J. Pouget, B. Valeur, J. Canceill, L. Jullien and J.-M. Lehn, Multichromophoric cyclodextrins. 2. Inhomogeneous spectral broadening and directed energy hopping, J. Phys. Chem., 1993, 97, 11376–11379
M. N. Berberan-Santos, J. Canceill, E. Gratton, L. Jullien, J.-M. Lehn, P. Peter So, J. Sutin and B. Valeur, Multichromophoric cyclodextrins. 3. Investigation of dynamics of energy hopping by frequency-domain fluorometry, J. Phys. Chem., 1996, 100, 15–20
M. N. Berberan-Santos, P. Choppinet, A. Fedorov, L. Jullien and B. Valeur, Multichromophoric cyclodextrins. 6. Investigation of excitation energy hopping by Monte-Carlo simulations and time-resolved fluorescence anisotropy, J. Am. Chem. Soc., 1999, 121, 2526–2533.
L. Jullien, J. Canceill, B. Valeur, E. Bardez and J.-M. Lehn, Antenna effect in multichromophoric cyclodextrins, Angew. Chem., Int. Ed. Engl., 1994, 33, 2438–2439
L. Jullien, J. Canceill, B. Valeur, E. Bardez, J. P. Lefèvre, J.-M. Lehn, V. Marchi-Artzner and R. Pansu, Multichromophoric cyclodextrins. 4. Light conversion by antenna effect, J. Am. Chem. Soc., 1996, 118, 5432–5442
D. M. Gravett and J. E. Guillet, Synthesis and photophysics of a water-soluble, naphthalene-containing β-cyclodextrin, J. Am. Chem. Soc., 1993, 115, 5970–5974.
G. Mc Dermott, S. M. Prince, A. A. Freer, M. Z. Hawthornthwaite-Lawless, X. X. Papiz, R. J. Cogdell and N. W. Isaacs, Crystal structure of an integral membrane light-harvesting complex from photosynthetic bacteria, Nature, 1995, 374, 517–521
X. Hu and K. Schulten, How Nature Harvests Sunlight, Physics Today, 1997, 50, 28–34.
N. Chattopadhyay, B. Haldar, A. Mallick and S. Sengupta, Photophysical studies on multichromophoric cyclotriphosphazenes, trinuclear excimer formation in hexakis(2-naphthyloxy)cyclotriphos-phazene, Tetrahedron Lett., 2005, 46, 3089–3092.
P. Wang, L. Jullien, B. Valeur, J.-S. Filhol, J. Canceill and J.-M. Lehn, Multichromophoric cyclodextrins. 5. Antenna-induced unimolecular photoreactions; Photoisomerisation of a nitrone, New J. Chem., 1996, 20, 895–907
M. Nowakowska, N. Loukine, D. M. Gravett, N. A. D. Burke and J. E. Guillet, A novel antenna cyclodextrin: synthesis and photosensitized reaction of an included guest, J. Am. Chem. Soc., 1997, 119, 4364–4368.
P. Choppinet, L. Jullien and B. Valeur, Multichromophoric cyclodextrins as fluorescent sensors. Interaction of heptachromophoric β-cyclodextrins with surfactants, J. Chem. Soc., Perkin. Trans. 2, 1999, 249–255.
E. D. Rekaï, J. B. Baudin, L. Jullien, I. Ledoux, J. Zyss, M. Blanchard-Desce, A hyperpolar, multichromophoric cyclodextrin derivative: synthesis, and linear and nonlinear optical properties, Chem.-Eur. J., 2001, 7, 4395–40402.
I. Leray, J.-P. Lefèvre, J.-F. Delouis, J. Delaire and B. Valeur, Synthesis and photophysical and cation-binding properties of mono- and tetranaphthylcalix[4] arenes as highly sensitive and selective fluorescent sensors for sodium, Chem.-Eur. J., 2001, 7, 4590–4598
R. Métivier, I. Leray and B. Valeur, A highly sensitive and selective fluorescent molecular sensor for Pb(II) based on a calix[4]arene bearing four dansyl groups, Chem. Commun., 2003, 996–997
R. Métivier, I. Leray and B. Valeur, Photophysics of calixarenes bearing two or four fluorophores: charge, proton and energy transfers, Photochem. Photobiol. Sci., 2004, 3, 374–380
R. Métivier, I. Leray and B. Valeur, Lead and Mercury Sensing by Calixarene-Based Fluoroionophores Bearing Two or Four Dansyl Fluorophores, Chem.-Eur. J., 2004, 10, 4480–4490
B. Valeur and I. Leray, Ion-responsive supramolecular fluorescent systems based on multichromophoric calixarenes: A review, Inorg. Chim. Acta, 2007, 360, 765–774
J. S. Kim and D. T. Quang, Calixarene-Derived Fluorescent Probes, Chem. Rev., 2007, 107, 3780–3799.
O. S. Wolfbeis, The click reaction in the luminescent probing of metal ions, and its implications on biolabeling techniques, Angew. Chem., Int. Ed., 2007, 46, 2980–2982.
O. David, S. Maisonneuve and J. Xie, Generation of new fluorophore by Click chemistry: synthesis and properties of β-cyclodextrin substituted by 2-pyridyl triazole, Tetrahedron Lett., 2007, 48, 6527–6530.
H. C. Kolb, M. G. Finn and K. B. Sharpless, Click Chemistry: Diverse Chemical Function from a Few Good Reactions, Angew. Chem., Int. Ed., 2001, 40, 2004–2021.
C. W. Tornoe, C. Christensen and M. Meldal, Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(i)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides, J. Org. Chem., 2002, 67, 3057–3069.
E.-H. Ryu and Y. Zhao, Efficient Synthesis of Water-Soluble Calixarenes Using Click Chemistry, Org. Lett., 2005, 7, 1035–1037.
S. M. Nabavizadeh, Thermodynamic studies of the binding of bidentate nitrogen with methyltrioxorhenium (MTO) in CHCl3 solution, Dalton Trans., 2005, 1644–1648.
M. N. Berberan-Santos and B. Valeur, Luminescence decays with underlying distributions: general properties and analysis with mathematical functions, J. Lumin., 2007, 126, 263–272
M. N. Berberan-Santos, E. N. Bodunov and B. Valeur, Mathematical functions for the analysis of luminescence decays with underlying distributions. 1. Kohlrausch decay function (stretched exponential), Chem. Phys., 2005, 315, 171–182
M. N. Berberan-Santos, E. N. Bodunov and B. Valeur, Mathematical functions for the analysis of luminescence decays with underlying distributions. 2. Becquerel (compressed hyperbola) and related decay functions, Chem. Phys., 2005, 317, 57–62.
S. Huang, R. J. Clark and L. Zhu, Highly Sensitive Fluorescent Probes Zinc Ion Based on Triazolyl-Containing Tetradentate Coordination Motifs, Org. Lett., 2007, 9, 4999–5002.
L. B. Berlman, Handbook of Fluorescence Spectra of Aromatic Molecules, Academic Press, London, 1965.
H. Gampp, M. Maeder, C. J. Meyer, A. D. Zuberbühler, Calculation of equilibrium constants from multiwavelength spectroscopic data. 1. Mathematical considerations, Talanta, 1985, 32, 95–101.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Souchon, V., Maisonneuve, S., David, O. et al. Photophysics of cyclic multichromophoric systems based on β-cyclodextrin and calix[4]arene with appended pyridin-2′-yl-1,2,3-triazolegroups. Photochem Photobiol Sci 7, 1323–1331 (2008). https://doi.org/10.1039/b810465d
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1039/b810465d