Published August 18, 2009 | Version v1
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Reversible Molecular Logic: A Photophysical Example of a Feynman Gate

Authors/Creators

  • 1. Departamento de Ingeniería Química, Química Física y Química Orgánica, Universidad de Huelva, Campus de El Carmen s/n, 21071 Huelva (Spain), Fax: (+)34 959 21 99 83
  • 2. Departamento de Química Orgánica, Universidad de Málaga, Campus Teatinos, 29071 Málaga (Spain), Fax: (+) 34 952 13 19 41

Description

The first molecular realization of a reversible logic operation with a simple cocktail of two classical fluorophores is demonstrated (see figure). Protons and anions, which serve as inputs, trigger independent fluorescence answer signals. Thus, XOR and YES gates are straightforward implemented, resulting in reversible logic behavior.

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Additional details

Identifiers

DOI
10.1002/cphc.200900375

Dates

Created
2009-08-18
Published

References

  • [1] P. Ball, Nature 2000, 406, 118. [2] G. E. Moore, Electronics 1965, 38, 114. [3] a) A. P. de Silva, H. Q. N. Gunaratne, C. P. McCoy, Nature 1993, 364, 42; b) C. P. Collier, E. W. Wong, M. Belohradský, F. M. Raymo, J. F. Stoddart, P. J. Kuekes, R. S. Williams, J. R. Heath, Science 1999, 285, 391; c) V. Balzani, A. Credi, M. Venturi, Chem. Eur. J. 2002, 8, 5524; d) E. R. Kay, D. A. Leigh, F. Zerbetto, Angew. Chem. 2007, 119, 72; Angew. Chem. Int. Ed. 2007, 46, 72. [4] a) U. Pischel, Angew. Chem. 2007, 119, 4100; Angew. Chem. Int. Ed. 2007, 46, 4026; b) K. Szaciłowski, Chem. Rev. 2008, 108, 3481. [5] R. Landauer, IBM J. Res. Develop. 1961, 5, 183. [6] a) C. H. Bennett, IBM J. Res. Develop. 1973, 17, 525; b) J. P. Klein, T. H. Leete, H. Rubin, BioSystems 1999, 52, 15. [7] P. Ball, Nature 2006, 440, 398. [8] E. Pérez-Inestrosa, J.-M. Montenegro, D. Collado, R. Suau, J. Casado, J. Phys. Chem. C 2007, 111, 6904. [9] D. Margulies, G. Melman, A. Shanzer, Nature Mater. 2005, 4, 768. [10] R. P. Feynman, Optics News 1985, 11, 11. [11] a) A. P. de Silva, N. D. McClenaghan, J. Am. Chem. Soc. 2000, 122, 3965; b) Z. Wang, M. A. Palacios, G. Zyryanov, P. Anzenbacher Jr., Chem. Eur. J. 2008, 14, 8540. [12] a) A. P. de Silva, H. Q. N. Gunaratne, J.-L. Habib-Jiwan, C. P. McCoy, T. E. Rice, J.-P. Soumillion, Angew. Chem. 1995, 107, 1889; Angew. Chem. Int. Ed. Engl. 1995, 34, 1728; b) Y. Q. Gao, R. A. Marcus, J. Phys. Chem. A 2002, 106, 1956. [13] F. M. Pfeffer, M. Seter, N. Lewcenko, N. W. Barnett, Tetrahedron Lett. 2006, 47, 5241. [14] T. Gunnlaugsson, P. E. Kruger, P. Jensen, F. M. Pfeffer, G. M. Hussey, Tetrahedron Lett. 2003, 44, 8909. [15] R. Ferreira, P. Remón, U. Pischel, J. Phys. Chem. C 2009, 113, 5805. [16] T. C. Barros, G. R. Molinari, P. Berci Filho, V. G. Toscano, M. J. Politi, J. Photochem. Photobiol. A: Chem. 1993, 76, 55. [17] A. Credi, V. Balzani, S. J. Langford, J. F. Stoddart, J. Am. Chem. Soc. 1997, 119, 2679. [18] A. Coskun, E. Deniz, E. U. Akkaya, Org. Lett. 2005, 7, 5187. [19] a) J. C. Beeson, M. E. Huston, D. A. Pollard, T. K. Venkatachalam, A. W. Czarnik, J. Fluorescence 1993, 3, 65; b) G. Greiner, I. Maier, J. Chem. Soc. Perkin Trans. 2 2002, 1005; c) F. Loiseau, C. Di Pietro, S. Campagna, M. Cavazzini, G. Marzanni, S. Quici, J. Mater. Chem. 2005, 15, 2762. [20] A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher, T. E. Rice, Chem. Rev. 1997, 97, 1515. [21] MAA requires only one equivalent of protons (10 μM) to show its full fluorescence enhancement. However, in order to operate both fluorophores with the same inputs, I1 was chosen much higher (150 mM) because of the much weaker basicity of ANAP. Noteworthy, the fluorescence of MAAH+ remains at the same high level at this high proton concentration, which is in favor for the implemented logic YES operation. [22] Upon sole addition of water corresponding to the amount introduced with 200 mM tetra-n-butylammoniumhydroxide-30-hydrate, i.e., 6 M water, the fluorescence intensity of ANAP at 509 nm reduces to ca. 50% of the value in presence of both inputs (I1=I2=1), i.e., 150 mM protons and 50 mM hydroxide ions. [23] A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, P. L. M. Lynch, New J. Chem. 1996, 20, 871. [24] The following equation was used to determine the critical radius R0: R0 6=8.8×10−28×ΦD×κ2×n−4×J, with energy donor fluorescence quantum yield in absence of any quenching ΦD=0.51 (for MAAH+ in acetonitrile), orientation factor κ2=2/3, refractive index n=1.3441, spectral overlap integral J=2.7×10−11 cm6mol−1. [25] Noteworthy, PET from piperidine to the singlet-excited 4-amino-1,8- naphthalimide part of ANT-PIP-ANAP is not supposed to happen. This based on molecular electric field effects (cf. ref. 12a) and theoretical considerations of the electronic coupling matrix element (cf. ref. 12b). [26] A. Khosravi, S. Moradian, K. Gharanjig, F. A. Taromi, Dyes Pigments 2006, 69, 79. [27] C. A. Parker, T. A. Joyce, Chem. Commun. (London) 1967, 744. [28] J. V. Morris, M. A. Mahaney, J. R. Huber, J. Phys. Chem. 1976, 80, 969.