Abstract
A naphthalene diimide acceptor 1 bearing a pyridine group linked directly (a series) or through a —CH2CH2— spacer (b series) coordinated axially to a metallotetraarylporphyrin (MP) undergoes fast photoinduced electron transfer (in the case of MP = Zn(II)TTP) while the kinetically more stable ruthenium complexes (MP = Ru(CO)TPP) have been used to illustrate the correlation between the distance of probe protons from the porphyrin plane and the change in chemical shift (Δδ) upon coordination. Changes in the emission spectra at 650 nm (λ ex= 400 nm) upon the addition of Zn(II) ions and/or 1b to TTPH2 can be interpreted in a truth table to illustrate a NAND gate.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A.K. Burrell, D.L. Officer, P.G. Plieger, and D.C.W. Reid: Chem. Rev. 101, 2751 (2001).
Y. Tong, D.G. Hamilton, J.-C. Meillon, and J.K.M. Sanders: Org. Lett. 1, 1343 (1999).
B.J. Holliday and C.A. Mirkin: Angew. Chem. Int. Ed. 40, 2022 (2001).
C.C. Mak, N. Bampos, S.L. Darling, M. Montalti, L. Prodi, and J.K.M. Sanders: J. Org. Chem. 66, 4476 (2001); (b) E. Stulz, C.C. Mak, and J.K.M. Sanders: J. Chem. Soc., Dalton Trans. 5, 604 (2001).
L. Giribabu, T.A. Rao, and B.G. Maiya: Inorg. Chem. 38, 4971 (1999).
For examples of porphyrin-diimide systems see: (a) M.J. Gunter, N. Bampos, K.D. Johnstone, and J.K.M. Sanders: New. J. Chem. 25, 166 (2001); (b) H.L. Anderson, C.A. Hunter, and J.K.M. Sanders: J. Chem. Soc. Chem. Commun. 226 (1989); (c) J.A. Cowan, J.K.M. Sanders, G.S. Beddard, and R.J. Harrison: J. Chem. Soc. Chem. Commun. 55 (1987); (d) H. Shiratori, T. Ohno, K. Nozaki, I. Yamazaki, Y. Nishimura, and A. Osuka: J. Org. Chem. 65, 8747 (2000).
A number of examples of electron transfer in simple diads formed by self-assembly using metalloporphyrin coordination have appeared in the literature: (a) C.A. Hunter, J.K.M. Sanders, G.S. Beddard, and S. Evans: J. Chem. Soc. Chem. Commun. 1765 (1989); (b) F. D'Souza, G.R. Deviprasad, M.E. Zander, M.E. El-Khouly, M. Fujitsuka, and O. Ito: J. Phys. Chem. B. 106, 4952 (2002); (c) L. Flamigni and M.R. Johnston: New. J. Chem. 25, 1368 (2001).
C.J. Zhong, W.S.V. Kwan, and L.L. Miller: Chem. Mater. 4, 1423 (1992).
G. Magnus and R. Levine: J. Am. Chem. Soc. 78, 4127 (1956).
S.J. Langford, M.A.P. Lee, K.J. Macfarlane, and J.A. Weigold: J. Incl. Phenom. 41, 135 (2001).
M. Nappa and J.S. Valentine: J. Am. Chem. Soc. 100, 5075 (1978).
F.J.C. Rossotti and H. Rossotti: The Determination of Stability Constants, McGraw-Hill, New York (1961).
K.M. Kadish, L.R. Shiue, R.K. Rhodes, and L.A. Bottomley: Inorg. Chem. 20, 1274 (1981).
Z.D. Hill and P. MacCarthy: J. Chem. Educ. 63, 162 (1986).
B.G. Maiya, N. Bampos, A.A. Kumar, N. Feeder, and J.K.M. Sanders: New J. Chem. 25, 801 (2001).
G.D. Fallon, S.J. Langford, M.A.P. Lee, and E. Lygris: Inorg. Chem. Commun. 5, 715 (2002).
Because of the lack of structural information by X-ray crystallography, molecular modelling (Insight II) has been used as a suitable approximation to determine the distances between hydrogen atoms to the porphyrin plane. Ru-N distances were taken from published X-ray crystal structure data, see: K. Funatsu, A. Kimura, T. Imamura, A. Ichimura, and Y. Sasaki: Inorg. Chem. 36, 1625 (1997).
E. Steiner and P.W. Fowler: Chem. Phys. Lett. 364, 259 (2002).
K. Cross and M.J. Crossley: Aust. J. Chem. 45, 991 (1992).
D.V. O'Connor and D. Phillips: Time-Correlated Single Photon Counting, Academic, London (1984).
D. Parker and J.A.G. Williams: Chem. Commun. 245 (1998).
V. Balzani, M. Venturi, and A. Credi: Molecular Devices and Machines-A Journey into the Nanoworld, Wiley-VCH, Weinheim (2003) chapter 9.
A.P. de Silva and N.D. McClenaghan: Chem. Eur. J. 8, 4935 (2002); (b) H. Xu, X. Xu, R. Dabestani, G.M. Brown, L. Fan, S. Patton, and H. Ji: J. Chem. Soc., Perkin Trans. 2, 636 (2002). (c) M.N. Stojanovic, T.E. Mitchell, and D. Stefanovic: J. Am. Chem. Soc. 124, 3555 (2002); (d) A.P. de Silva, H.Q.N. Gunaratne, and C.P. McCoy: Nature 364, 42 (1997).
M.M. Mano: Digital Design, Prentice Hall, New Jersey, 2nd edn. (1991).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Ghiggino, K.P., Hutchison, J.A., Langford, S.J. et al. Modulating Electron Transfer in a Simple Bichromophoric System Employing Axial-Ligation as an Organising Precept. Journal of Inclusion Phenomena 49, 27–32 (2004). https://doi.org/10.1023/B:JIPH.0000031109.90104.24
Issue Date:
DOI: https://doi.org/10.1023/B:JIPH.0000031109.90104.24