Abstract
The fluorescence technique has been applied to the study of the metal cation binding of three photoresponsive complexing systems able to form 1:1 and 1:2 (ligand:cation) complexes. These are constituted of bisarylcyclophanes denoted: AAO5O5 (bis 9, 10-dioxyanthrylcoronand), BBO5O5 (bis 1,4-dioxyphenylcoronand) and TTO5O5 (bis l-methylene-4-oxyphenyl-coronand) The metal cation binding ability in the singlet excited state is shown to increase for AAO5O5 owing to the formation of a long lived excimer and decrease for BBO5O5 and TTO5O5; this diminution is interpreted as a transitory photodecomplexation between the metal cations and the phenolic oxygen atoms, but the metal cations are believed to remain in close proximity to the macrocycle as shown by fluorescence anisotropy measurements The determination of the association constants K11 and K12 allow a discussion of the cooperative effects (positive or negative) found in the ground state and in the excited state.
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References
Wolfbeis OS (1991) Fiber optic chemical sensors and biosensors CRC Press, vols 1 and 2
Desvergne JP, Czarnik AW (1997) Chemosensors of ion of molecule recognition NATO ASI Series C, 492 Kluwer Academic Publishers, Dordrecht
De Silva AP, Ghunaratne HQN, Gunnlaugsson T, Huxley AJM, Rademacher CP, Rice TE (1997) Signaling recognition events with fluorescent sensors and switches Chem Rev 97:1515–1566 and references cited therein
Fabbrizzi L, Poggi A (1995) Sensors and switches from supramolecular chemistry Chem Soc Rev 197–202
Birks JB (1970) Photophysics of aromatic molecules Wiley-Interscience, London
Lehn JM (1995) Supramolecular chemistry — concepts and perspectives VHC, Weinheim
Létard JF, Delmond S, Lapouyade R, Braun D, Rettig W, Kreissler M (1995) New intrinsic fluoroionophores with dual fluorescence: DMABN-crown4 and DMABN-crown5 Rec Trav Chim Pays-Bas 114:517–527
Martin MM, Plaza P, Meyer YH, Badaoui F, Bourson J, Lefevre JP, Valeur B (1996) Steady-state and picosecond spectroscopy of Li+ or Ca2+ complexes with a crowned merocyanine. Reversible photorelease of cations J Phys Chem 100:6879–6888
Izatt RM, Bradshaw JS, Nielsen SA, Lamb JD, Christensen JJ, Sen D ( 1985) Thermodynamic and kinetic data for cation-macrocycle interaction Chem Rev 85:271–339
Bouas-Laurent H, Castellan A, Desvergne JP (1980) From anthracene photodimerization to jaw photochromic materials and photocrowns Pure Appl Chem 52:2633–2648 and references cited therein
Castellan A, Desvergne JP, Bouas-Laurent H (1980) Kinetic study of photophysical and photochemical processes in α, ω)-(bis-9-anthryl) n alkanes (ethane to decane) at room temperature Chem Phys Lett 76:390–397
Marquis D, Desvergne JP, Bouas-Laurent H (1995) Photoresponsive supramolecular systems: synthesis, photophysical and photochemical study of bis-(9,10-anthracenediyl) coronands AAOnOn J Org Chem 60:7984–7996
Ferguson J (1986) Absorption spectroscopy of sandwich dimers and cyclophanes Chem Rev 86:957–982
Bouas-Laurent H, Desvergne JP, Fages F, Marsau P (1991) Tunable fluorescence of some macrocyclic anthracenophanes In: Schneider HJ, Dürr H (eds) Frontiers in supramolecular organic chemistry and photochemistry VCH, Weinheim, pp 265–286
Connors KA (1987) Binding constants The measurement of molecular complex stability. Wiley, New-York
Lehn JM (1973) Design of organic complexing agents Strategies towards properties. Structure and Bonding 16:2–112
Pauling L (1945) The nature of the chemical bond, 2nd edn Cornell University Press, Ithaca, New York
Marquis D, Greiving H, Desvergne JP, Lahrahar N, Marsau P, Hopf H, Bouas-Laurent H (1997) From p-dimethoxybenzene to crown benzenophanes (4) Cation-complexing properties of bis-(p-phenylene-34-crown-10); a structural and spectrophotometric study. Liebigs Ann Recueil 97–106
Slawin AMZ, Spencer N, Stoddart JF, Williams DJ (1987) Complexation of diquat by a bisparaphenylene-34-crown-10 derivative JCS Chem Commun 1061–1064
Kimura K, Kaneshige M, Yokoyama M (1995) Cation complexation, photochromism, and photoresponsive ion-conducting behavior of crowned malachite green leuconitrile Chem Mater 7:945–950
Desvergne JP, Bouas-Laurent H, Perez-Inestrosa E, Marsau P, Cotrait M (1999) Photoinduced control of cation binding ability of non-conjugated bichromophoric receptors Coord Chem Rev 185/186:357–371
McCullough JJ, Yeroushalmi S (1983) Quenching of fluorescence by substituted ethylenes. Substituent and salt effects as criteria of quenching mechanism JCS Chem Commun 254–256
PC MODEL for IBM 386 or 486, Serena Software, Bloomington, USA
Chang YJ, Castner EW Jr (1994) Deuterium isotope effects on the ultrafast relaxation of formamide and N,N-dimethylformamide J Phys Chem 98:9712–9722
Buchhauser J, Groß T, Karger N, Lüdemann HD ( 1999) Self diffusion in CD4 and ND3: with notes on the dynamic isotope effect in liquids J Chem Phys 110:3037–3042
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Desvergne, JP., Perez-Inestrosa, E., Bouas-Laurent, H., Jonusauskas, G., Oberlé, J., Rullière, C. (2001). Phototunable Metal Cation Binding Ability of Some Fluorescent Macrocyclic Ditopic Receptors. In: Valeur, B., Brochon, JC. (eds) New Trends in Fluorescence Spectroscopy. Springer Series on Fluorescence, vol 1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-56853-4_8
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DOI: https://doi.org/10.1007/978-3-642-56853-4_8
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