pH-tunable equilibria in azocrown ethers with histidine moieties

Bioelectrochemistry

Volumn 71, Issue 1, 2007, Pages 99-106

  Jabłonowska, Elzbieta ^a   Pałys, Barbara ^a   Wagner Wysiecka, Ewa ^c   Jamrógiewicz, Marzena ^c   Biernat, Jan F ^b   Bilewicz, Renata ^a  

^a UNIVERSITY OF WARSAW   (Poland)

^b GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

^c NONE

Author keywords

Azocompound; Azocrown ether; Histidine derivative; Macrocycle; Tautomeric equilibria; Voltammetry

Indexed keywords

ELECTROCHEMICAL CELLS; ELECTRODES; HYDRAZINE; MERCURY (METAL); PROTONS; REDUCTION; VOLTAMMETRY;

AZOCOMPOUND; AZOCROWN ETHER; HISTIDINE DERIVATIVE; MACROCYCLE; TAUTOMERIC EQUILIBRIA;

ETHERS;

ETHER DERIVATIVE; HISTIDINE; HYDRAZINE; N ACETYLHISTIDINE; PROTON;

ARTICLE; ELECTROCHEMICAL ANALYSIS; ELECTROCHEMISTRY; NUCLEAR MAGNETIC RESONANCE; PH; PHOTOACTIVATION; ULTRAVIOLET RADIATION;

AZO COMPOUNDS; BENZOQUINONES; CARBOXYLIC ACIDS; CROWN ETHERS; ELECTROCHEMISTRY; ELECTRODES; HISTIDINE; HYDRAZINES; HYDRAZONES; HYDROGEN-ION CONCENTRATION; IMIDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; MERCURY; OXIDATION-REDUCTION; PROTONS; SOLUTIONS; SPECTROPHOTOMETRY, ULTRAVIOLET; SPECTRUM ANALYSIS, RAMAN; SURFACE PROPERTIES;

EID: 34548490103     PISSN: 15675394     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bioelechem.2006.09.005     Document Type: Article

References (41)

1. Kano K., Tanaka Y., Ogawa T., Shimomura M., Okahata Y., and Kunitake T. Photoresponsive membranes. Regulation of membrane properties by photoresponsible cis-trans isomerization of azobenzenes. Chem. Lett. (1980) 421-424
2. Shinkai S., and Manabe O. Photocontrol of ion extraction and ion-transport by photofunctional crown ethers. Top. Curr. Chem. 121 (1984) 67-104
3. Einaga Y., Gu Z.-Z., Hayami S., Fujishima A., and Sato O. Reversible photoinduced switching of magnetic properties at room temperature of iron oxide particles in self-assembled films containing azobenzene. Thin Solid Films 374 (2000) 109-113
4. Ikeda T., and Tstsumi O. Optical switching and image storage by means of azobenzene liquid-crystal films. Science 268 (1995) 1873-1875
5. Nagele T., Hoche R., Zinth W., and Wachtveitl J. Femtosecond photoisomerization of cis-azobenzene. Chem. Phys. Lett. 272 (1997) 489-495
6. Moss R.A., and Jiang W. Thermal modulation of photoisomerization in double-azobenzene-chain liposomes. Langmuir 13 (1997) 4498-4501
7. Ren Y., Tian Y., Sun R., Xi S., Zhao Y., and Huang X. Structure and photoisomerization of the Z-type Langmuir-Blodgett films of a new series of azo-containing chiral copolymers. Langmuir 13 (1997) 5120-5124
8. Wang R., Iyoda T., Tryk D.A., Hashimoto K., and Fujishima A. Electrochemical modulation of molecular conversion in an azobenzene-terminated self-assembled monolayer film: an in situ UV-visible and infrared study. Langmuir 13 (1997) 4644-4651
9. Liu Z.F., Zhao C.X., Tang M., and Cai S.M. Electrochemistry of cis-azobenzene chromophore in coulombically linked self-assembled monolayer-Langmuir-Blodgett composite monolayers. J. Phys. Chem. 100 (1996) 17337-17344
10. Zhang J., Zhao J., Zhang H.L., Li H.L., and Liu Z.F. Structural evaluation of azobenzene-functionalized self-assembled monolayers on gold by reflectance FTIR spectroscopy. Chem. Phys. Lett. 271 (1997) 90-94
11. Herr B.R., and Mirkin C.A. Self-assembled monolayers of ferrocenylazobenzenes: monolayer structure vs response. J. Am. Chem. Soc. 116 (1994) 1157-1158
12. Caldwell W.B., Chen K.M., Herr B.R., Mirkin C.A., Hulteen J.C., and Duyne R.P.V. Self-assembled monolayers of ferrocenylazobenzenes on Au(111)/mica films: surface-enhanced Raman scattering response vs surface morphology. Langmuir 10 (1994) 4109-4115
13. Caldwell W.B., Campbell D.J., Chen K.M., Herr B.R., Mirkin C.A., Malik A., Durbin M.K., Dutta P., and Huang K.G. A highly ordered self-assembled monolayer film of an azobenzenealkanethiol on Au(111): electrochemical properties and structural characterization by synchrotron in-plane X-ray diffraction, atomic force microscopy, and surface-enhanced Raman spectroscopy. J. Am. Chem. Soc. 117 (1995) 6071-6082
14. Liu Z.F., Hashimoto K., and Fujishima A. Photoelectrochemical information storage using an azobenzene derivative. Nature 347 (1990) 658-660
15. Liu Z.F., Hashimoto K., and Fujishima A. Kinetic studies on the thermal cis-trans isomerization of an azo compound in the assembled monolayer film. J. Phys. Chem. 96 (1992) 1875-1880
16. Liu Z.F., Loo B.H., Hashimoto K., and Fujishima A. A novel photoelectrochemical hybrid "one-way" process observed in the azobenzene system. J. Electroanal. Chem. 297 (1991) 133-144
17. Bilewicz R. Molecular design of electrode surface for electoanalytical chemistry. Ann. Chim. 87 (1997) 53-66
18. Biernat J.F., Luboch E., Cygan A., Simonov Y.A., Dvorkin A.A., Muszalska E., and Bilewicz R. Synthesis, x-ray structure and electochemical properties of a new crown ether with a cis azo unit in the macrocycle. Tetrahedron 48 (1992) 4399-4406
19. Luboch E., Biernat J.F., Muszalska E., and Bilewicz R. 13-membered crown ethers with azo or azoxy unit in the macrocycle - synthesis, membrane electrodes, voltammetry and Langmuir monolayers. Supramol. Chem. 5 (1995) 201-210
20. Zawisza I., Luboch E., Biernat J.F., and Bilewicz R. Properties of Z and E isomers of azocrown ethers in monolayer assemblies at the air-water interface. Thin Solid Films 348 (1999) 173-179
21. Huesmann H., Maack J., and Möbius D. Molecular cis/trans isomerization of an azobenzene containing 13-azo-phane-3 in monolayer, J.F. Biernat. Sens. Actuators B 29 (1995) 148-153
22. Muszalska E., Bilewicz, and R. Adsorptive stripping analysis and monolayer properties of crown ethers with an azo unit in the macrocycle. Analyst 119 (1994) 1235-1238
23. Goldenberg L.M., Biernat J.F., and Petty M.C. Electro- and photochemistry of 13-membered azocrowns in solution and as Langmuir-Blodgett films. Langmuir 14 (1998) 1236-1241
24. Zawisza I., Bilewicz R., Luboch E., and Biernat J.F. Langmuir-Blodgett films of azocrown ethers on electrodes - voltammetric recognition of isomers. J. Electroanal. Chem. 471 (1999) 156-166
25. Zawisza I., Bilewicz R., Luboch E., and Biernat J.F. Voltammmetric recognition of cis (Z) and trans (E) isomers of azobenzene and azocrown ethers. Supramol. Chem. 9 (1998) 277-287
26. Janus K., Sworakowski J., Olszowski A., Lewanowicz A., Lipiński J., Luboch E., and Biernat J.F. Kinetics of a photochromic reaction in a dibenzoazo crown ether in solution and in polymer matrices. Adv. Mater. Opt. Electron. 9 (1999) 181-187
27. Zawisza I., Bilewicz R., Luboch E., and Biernat J.F. Effect of binding cations on the electorchemical behavior of azocrown ethers in Langmuir-Blodgett films. J. Chem. Soc., Dalton Trans. 4 (2000) 499-503
28. Zawisza I., Bilewicz R., Moncelli M.R., and Guidelli R. Electrochemistry of Langmuir-Blodgett and self-organized monolayers of an azocrown ether, both pure and mixed with a phospholipid. J. Electroanal. Chem. 509 (2001) 31-41
29. Luboch E., Biernat J.F., Simonov Y.A., and Dvorkin A.A. Synthesis and electrode properties of 16-membered azo- and azoxycrown ethers. Structure of tribenzo-16-azocrown-6. Tetrahedron 54 (1998) 4977-4990
30. Biernat J.F., Luboch E., Skwierawska A., Bilewicz R., and Muszalska E. Azocrown ethers as ion sensing compounds. Biocyb. Biomed. Eng. 16 (1996) 125-135
31. Skwierawska A., Inerowicz H.D., and Biernat J.F. Chromogenic proton-dissociable azocrown ether reagents for lithium ions. Tetrahedron Lett. 39 (1998) 3057-3060
32. Wagner-Wysiecka E., Skwierawska A., Kravtsov V.Ch., and Biernat J.F. New class of chromogenic proton-dissociable azocrown reagents for alkali metal ions. J. Supramol. Chem. 1 2 (2001) 77-85
33. Luboch E., Bilewicz R., Kowalczyk M., Wagner-Wysiecka E., and Biernat J.F. Azomacrocyclic compounds. In: Gokel G.W. (Ed). Advances in Supramolecular Chemistry vol. 9 (2003), Cerberus Press Inc. 73-163
34. Luboch E., Poleska-Muchlado Z., Jamrógiewicz M., and Biernat J.F. In: Gloe K. (Ed). Macrocyclic Chemistry, Current Trends and Future Perspectives (2005), Springer 203-218 Chapter 13. Cyclodextrin Combinations with Azocompounds
35. Ovchinnikov Y.A., Ivanov V.T., and Shkrob A.M. Membrane Active Complexones (1974), Elsevier, New York
36. Pressman B.C. Biological applications of ionophores. Ann. Rev. Biochem. 45 (1976) 501-530
37. Hay R.W. Bio-Inorganic Chemistry (1984), Ellis Horwood, Chichester
38. Wagner-Wysiecka E., Luboch E., Kowalczyk M., and Biernat J.F. Chromogenic macrocyclic derivatives of azoles - synthesis and properties. Tetrahedron 59 (2003) 4415-4420
39. Luboch E., Wagner-Wysiecka E., and Biernat J.F. Chromogenic azocrown ethers with peripheral alkyl, alkoxy, hydroxy or dimethylamino group. J. Supramol. Chem. 2 (2003) 279-291
40. Herbst R.M., and Shemin D. Acetylglycine, organic syntheses. Coll. II (1947) 11-12
41. Maciejewska D., and Skulski L. UV-Vis solution spectra of 2-arylazoimidazoles and of their 1-N-methyl derivatives as compared with those of the respective azobenzenes. Exemplary application of empirical methods of spectral characterization of some complex aryazo substituted groups. Pol. J. Chem. 57 (1983) 971-984