Optimization and chemical control of porphyrin-based molecular wires and switches

Annals of the New York Academy of Sciences

Volumn 852, Issue , 1998, Pages 1-21

  Hush, Noel S ^a,b   Reimers, Jeffrey R ^a   Hall, Lachlan E ^a   Johnston, Lesley A ^c   Crossley, Maxwell J ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

^b UNIVERSITY OF SYDNEY   (Australia)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE; AROMATIC COMPOUND; HYDROQUINONE; PORPHYRIN; PYRIDONE DERIVATIVE;

CHEMICAL MODIFICATION; CONFERENCE PAPER; ELECTRONICS; PH; PROTON TRANSPORT;

EID: 0031850727     PISSN: 00778923     EISSN: None     Source Type: Book Series    
DOI: 10.1111/j.1749-6632.1998.tb09861.x     Document Type: Conference Paper

References (36)

1. ROTH, S. & C. JOACHIM. 1997. Atomic and molecular wires. Kluwer. Dordrecht.
2. RATNER, M.A., B. DAVIS, M. KEMP, V. MUJICA, A. ROITBERG & S. YALIRAKI. 1998. Ann. New York Acad. Sci. This volume.
3. MUJICA, V., M. KEMP, A. ROITBERG & M.A. RATNER. 1996. Current-voltage characteristics of molecular wires: Eigenvalue staircase, Coulomb blockade, and rectification. J. Chem. Phys. 104: 7296-7306.
4. BUMM, L. A., J.J. ARNOLD, M.T. CYGAN, T.D. DUNBAR, T.P. BURGIN, L. JONES II, D.L. ALLARA, J.M. TOUR & P.S. WEISS. 1996. Are single molecular wires conducting?. Science 271: 1705-1707.
5. REED, M.A., C. ZHOU, C.J. MULLER, T.P. BURGIN & J.M. TOUR. 1997. Conductance of a molecular junction. Science 278: 252-254.
6. REIMERS, J.R. & N.S. HUSH. 1990. Electron and energy transfer through bridged systems. V. The electronic structure of the bis-pentaammineruthenium complexes of α,ω-dipyridyl trans-polyenes in nitrobenzene. Inorg. Chem. 29: 4510-4513.
7. JUNG, T.A., R.R. SCHLITTLER, J.K. GIMZEWSKI, H. TANG & C. JOACHIN. 1997. Controlled room-temperature positioning of molecules: Molecular flexure and motion. Science 271: 181.
8. CROSSLEY, M.J., S. MARTIN, L.A. JOHNSTON & C.W. TANSEY. 1998. Structural and electrical characterization of self-assembled monolayers of porphyrin-based molecular wires. Adv. Mater. In preparation.
9. CROSSLEY, M.J. & J.K. PRASHAR. 1997. Thiophene-appended porphyrin systems. Tetrahedron Lett. 38: 6751-6754.
10. AZUMI, R., M. MUTSUYOSHI, S. KURODA, L.G. KING & M.J. CROSSLEY. 1995. Orientation change of dimer-type porphyrin in Langmuir-Blodgett films caused by a trigger molecule. Langmuir 11: 4056-4060.
11. CROSSLEY, M.J., P.L. BURN, S.J. LANGFORD & J.K. PRASHAR. 1995. Porphyrins with appended phenanthroline units: A means by which porphyrin π systems can be connected to an external redox centre. J. Chem. Soc. Chem. Commun. 1921-1923.
12. HUSH, N.S., A.T. WONG, G.B. BACSKAY & J.R. REIMERS. 1990. Electron and energy transfer through bridged systems. VI. Molecular switches: The critical field in electric-field activated bistable molecules. J. Am. Chem. Soc. 112: 4192-4197.
13. CROSSLEY, M.J., L.A. JOHNSTON, J.R. REIMERS & N.S. HUSH. 1998. A laterally extended porphyrin switch incorporating a switchable unit. J. Am. Chem. Soc. In preparation.
14. CROSSLEY, M.J. & C.S. SHEEHAN. 1998. A new approach to molecular-sized rectifiers based on the Aviram-Ratner proposal. Synthesis of thienopyrazinobisporphyrins with an inbuilt electronic bias. J. Chem. Soc., Perkin Trans. I. Submitted for publication.
15. HOPFIELD, J.J., J.N. ONUCHIC & D.N. BERATAN. 1989. Electronic shift register memory based on molecular electron-transfer reactions. J. Phys. Chem. 93: 6350-6357.
16. GILAT, S.L., S.H. KAWAI & J.-M. LEHN. 1993. Light-triggered electrical and optical switching devices. J. Chem. Soc. Chem. Commun.: 1439-1442.
17. LEHN, J.-M. 1995. Supramolecular Chemistry. VCH. Weinheim.
18. CROSSLEY, M.J. & P.L. BURN. 1991. An approach to porphyrin-based molecular wires: Synthesis of a bis(porphyrin)tetraone and its conversion to a linearly conjugated tetrakisporphyrin system. J. Chem. Soc. Chem. Commun.: 1569-1571.
19. CROSSLEY, M. J., L.J. GOVENLOCK & J. PRASHAR. 1995. Synthesis of porphyrin-2,3,12,13- and 2,3,7,8-tetraones: Building blocks for the synthesis of extended porphyrin arrays. J. Chem. Soc. Chem. Commun.: 2379-2380.
20. LÜ, T.X., J.R. REIMERS, M.J. CROSSLEY & N.S. HUSH. 1994. Rigid fused oligoporphyrins as potential molecular wires: I. Geometry and connectivity of 1,4,5,8-tetraazaanthracene-bridged oligoporphyrins. J. Phys. Chem. 98: 11878-11884.
21. REIMERS, J.R., T.X. Lu, M.J. CROSSLEY & N.S. HUSH. 1996. The geometric and electronic structures of some simple porphyrinic molecular wires. Nanotechnology 7: 424-429.
22. REIMERS, J. R., T.X. LÜ, M.J. CROSSLEY & N.S. HUSH. 1995. The mechanism for inner-hydrogen migration in free base porphin: Ab initio MP2 calculations. J. Am. Chem. Soc. 117: 2855-2861.
23. REIMERS, J. R., L.E. HALL, M.J. CROSSLEY & N.S. HUSH. 1998. Rigid fused oligoporphyrins as potential versatile molecular wires: II. B3LYP and SCF calculated geometric and electronic properties of 98 oligoporphyrin and related molecules. J. Phys. Chem. B. Submitted for publication.
24. REIMERS, J.R. & N.S. HUSH. 1998. Density functional modelling of the electronic structure of the bis-pentaammineruthenium complexes of α,ω-dipyridyl trans-polyenes. Chem. Phys. Lett. In preparation.
25. ZENG, J., N.S. HUSH & J.R. REIMERS. 1996. Solvent effects on molecular and ionic spectra. IX. The change in dipole moment accompanying metal to ligand charge transfer in pentaamminopyridylruthenium(II). J. Phys. Chem. 100: 19292-19294.
26. HUSH, N.S. & J.R. REIMERS. 1995. Vibrational Stark spectroscopy 1. Basic theory and application to the CO stretch. J. Phys. Chem. 99: 15798-15805.
27. BACSKAY, G.B. & J.R. REIMERS. 1998. Solvent effects. In Encyclopaedia of Computational Chemistry. P. von R. Schleyer, Ed. Wiley. London. In press.
28. VILLAR, H.O. & M. DUPUIS. 1987. Bond order and valencies from ab initio wave-functions: Application to prototypical molecules and to the characterization of solitons in polyenes. Chem. Phys. Lett. 142: 59-66.
29. REIMERS, J.R., L.E. HALL, N.S. HUSH & K. SILVERBROOK. 1998. Chemical control of tautomerization-based molecular electronic and color switches. Ann. N. Y. Acad. Sci. This volume.
30. PADDON-ROW, M.N. & K.D. JORDAN. 1993. Analysis of the distance dependence and magnitude of the π+,π- and π+*, π-π splittings in a series of dietynyl[n]staffanes: An ab initio molecular orbital study. J. Am. Chem. Soc. 115: 2952-2960.
31. CURTISS, L.A., C.A. NALEWAY & J.R. MILLER. 1995. Superexchange pathway calculation of electronic coupling through cyclohexane spacers. J. Phys. Chem. 99: 1182-1193.
32. 2O. Inorg. Chem. 29: 3686-3697.
33. WOITELLIER, S., J.P. LAUNAY & C.W. SPANGLER. 1989. Invervalence transfer in pentaammineruthenium complexes of α,ω-dipyridyl polyenes. Inorg. Chem. 28: 758-762.
34. REIMERS, J.R. & N.S. HUSH. 1990. Electron and energy transfer through bridged systems. II. Tight binding linkages with zero asymmetric band gap. Chem. Phys. 146: 89-103.
35. REIMERS, J.R. & N.S. HUSH. 1989. Electron and energy transfer through bridged systems. I. Formalism. Chem. Phys. 134: 323-354.
36. REIMERS, J.R. & N.S. HUSH. 1994. Electron and energy transfer through bridged systems. III. Tight binding linkages with finite asymmetric band gap. J. Photochem. Photobiol. A 82: 31-46.