Photocatalytic reduction of aromatic azides to amines using CdS and CdSe nanoparticles

Photochemical and Photobiological Sciences

Volumn 3, Issue 9, 2004, Pages 859-863

  Warrier, Manoj ^a   Lo, Michael K F ^a   Monbouquette, Harold ^a   Garcia Garibay, Miguel A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AROMATIC COMPOUND; AZIDE; CADMIUM DERIVATIVE; CYSTEAMINE DERIVATIVE; FORMIC ACID DERIVATIVE; NANOPARTICLE; SELENIUM DERIVATIVE; SULFUR DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONTROLLED STUDY; ELECTRON TRANSPORT; OXIDATION REDUCTION REACTION; PARTICLE SIZE; PHOTOCATALYSIS; PHOTOCHEMICAL EFFICIENCY; PHOTOCHEMISTRY; PHOTODEGRADATION; PHOTOLYSIS; PRIORITY JOURNAL; QUANTUM YIELD; SEMICONDUCTOR; STRUCTURE ANALYSIS; SYNTHESIS; THEORETICAL MODEL;

EID: 7244223346     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b404268a     Document Type: Article

References (59)

1. H. Weller Colloidal Semiconductor Q-Particles: Chemistry in the transition region between solid state and molecules Angew. Chem., Int. Ed. Engl. 1993 32 41-53.
2. A. Hengelin Small-particle research: physicochemical properties of extremely small colloidal metal and semiconductor particles Chem. Rev. 1989 89 1861.
3. L. E. Brus Quantum crystallites and non-linear optics Appl. Phys. A 1991 53 465.
4. H. Weller Quantized semiconductor particles: a novel state of matter for materials science Adv. Mater. 1993 5 88-95.
5. L. Brus G. Hadjipanayis R. Siegel Electronic and optical properties of semiconductor nanocrystals: from molecules to bulk crystals Nanophase Mater. 1994 433-448.
6. A. Alivisatos Semiconductor clusters, nanocrystals, and quantum dots Science 1996 271 933-937.
7. T. Vossmeyer L. Katsikas M. Giersig I. Popovic K. Diesner A. Chemseddine A. Eychmuller H. Weller CdS nanoclusters: synthesis, characterization, size dependent oscillator strength, temperature shift of the excitonic transition energy, and reversible absorbance shift J. Phys. Chem. 1994 98 7665-7673.
8. Y. Wang N. Herron Nanometer-sized semiconductor clusters: materials synthesis, quantum size effects, and photophysical properties J. Phys. Chem. 1991 95 525-532.
9. D. Beydoun R. Amal G. Low S. McEvoy Role of nanoparticles in photocatalysis J. Nanoparticle Res. 1999 1 439-458.
10. H. Matsumoto H. Uchida T. Matsunaga K. Tanaka T. Sakata H. Mori H. Yoneyama Photoinduced reduction of viologens on size-separated CdS nanocrystals J. Phys. Chem. 1994 98 11549-11556.
11. A. Hagfeldt M. Gratzel M. Light-induced redox reactions in nanocrystalline systems Chem. Rev. 1995 95 49-68.
12. H. Yin Y. Wada T. Kitamura S. Yanagida Photoreductive dehalogenation of halogenated benzene derivatives using ZnS or CdS nanocrystallites as photocatalysts Environ. Sci. Technol. 2001 35 227-231.
13. B. Korgel H. Monbouquette Quantum confinement effects enable photocatalyzed nitrate reduction at neutral pH Using CdS nanocrystals J. Phys. Chem. B 1997 101 5010-5017.
14. B. Korgel H. Monbouquette Controlled synthesis of mixed core and layered (Zn, Cd)S and (Hg, Cd)S Nanocrystals within Phosphatidylcholine Vesicles Langmuir 2000 16 3588-3594.
15. M. Hoffmann S. Martin W. Choi D. Bahnemann Encironmental applications of semiconductor photocatalysis Chem. Rev. 1995 95 69-96.
16. H. Yoneyama Photoreduction of carbon dioxide on quantized semiconductor nanoparticles in solution Catal. Today 1997 39 169-175.
17. H. Inoue T. Torimoto T. Sakata H. Mori H. Yoneyama Effects of size quantizeation of zinc sulfide microcystallites on photocatalytic reduction of carbon dioxide Chem. Lett. 1990 1483-1486.
18. M. Green P. O’Brien Recent advances in the preparation of semiconductors as isolated nanometric particles: new routes to quantum dots Chem. Commun. 1999 2235-2241.
19. C. Murray D. Norris M. Bawendi Synthesis and characterization of nearly monodisperse CdE (E = sulfur, selenium, tellurium) semiconductor nanocrystallites J. Am. Chem. Soc. 1993 115 8706-8715.
20. 26 clusters Science 1995 267 1476-1479.
21. Y. Nosaka N. Ohta T. Fukuyama N. Fujii Size control of ultrasmall CdS particles in aqueous solution by using various thiols J. Colloid Interface Sci. 1993 155 23-29.
22. B. Degraff D. Gillespie R. Sundberg Phenyl nitrene. a flash photolytic investigation of the reaction with secondary amines J. Am. Chem. Soc. 1974 96 7491-7496.
23. A. Schrock G. Schuster Photochemistry of phenyl azide: chemical properties of the transient intermediates J. Am. Chem. Soc. 1984 106 5228-5234.
24. E. Leyva M. Platz G. Persy J. Wirz Photochemistry of phenyl azide: the role of singlet and triplet phenylnitrene as transient intermediates J. Am. Chem. Soc. 1986 108 3783-3790.
25. T. Liang G. Schuster Photochemistry of 3- and 4-nitrophenyl azide: detection and characterization of reactive intermediates J. Am. Chem. Soc. 1987 109 7803-7810.
26. G. Schuster M. Platz Photochemistry of phenyl azide Adv. Photochem. 1987 17 69-143.
27. M. Platz, Nitrenes, Wiley-Interscience, Hoboken, NJ, 2004, pp. 502–559.
28. J. Grimshaw, Photochemistry of Aryl Diazonium Salts, Triazoles and Tetrazoles, CRC Press, Boca Raton, FL, 2003, pp. 44.1–44.31.
29. Y. Li J. Kirby M. George M. Poliakoff G. Schuster 1,2-Didehydroazepines from the photolysis of substituted aryl azides: analysis of their chemical and physical properties by time-resolved spectroscopic methods J. Am. Chem. Soc. 1988 110 8092-8098.
30. N. Gritsan D. Tigelaar M. Platz A laser flash photolysis study of some simple para-substituted derivatives of singlet phenyl nitrene J. Phys. Chem. A 1999 103 4465-4469.
31. T. Liang G. Schuster Photochemistry of p-nitrophenyl azide: single-electron-transfer reaction of the triplet nitrene J. Am. Chem. Soc. 1986 108 546-548.
32. Thiols are known to be excellent hydrogen atom donors towards a wide range of reactive intermediates: S. Carroll B. Nay E. Scriven H. Suschitzky D. Thomas Decomposition of aromatic azides in ethanethiol Tetrahedron Lett. 1977 18 3175-3178.
33. S. Carroll B. Nay E. Scriven H. Suschitzky Decomposition of arylazides in piperidine Tetrahedron Lett. 1977 18 943-946.
34. E. Leyva M. Platz The temperature dependent photochemistry of phenyl azide in diethylamine Tetrahedron Lett. 1985 26 2147-2150.
35. H. Lund and O. Hammerich, Organic Electrochemistry, Marcel Dekker, Inc., New York, 4th edn., 2001.
36. A. Adamson Substitutiion Reactions of Reinecke’s Salt J. Am. Chem. Soc. 1958 80 3183-3189.
37. E. Wegner A. Adamson Photochemistry of complex ions. III. Absolute quantum yields for the photolyis of some aqueous chromium(III) complexes. Chemical actinometry in the long wavelength visible region J. Am. Chem. Soc. 1966 88 394-404.
38. S. Murov, I. Carmichael and G. Hug, Handbook of Photochemistry, Marcel Dekker, Inc., New York, 2nd edn., 1993.
39. This observation is reminiscent of the lack of substituent effects on the rate of rearrangement reported by Gritsan et al., in ref. 15.
40. T. Dannhauser M. O’Neil K. Johansson D. Whitten G. McLendon Photophysics of quantized colloidal semiconductors dramatic luminescence enhancement by binding of simple amines J. Phys. Chem. 1986 90 6074-6076.
41. L. Spanhel M. Haase H. Weller A. Henglein Photochemistry of Colloidal Seminconductors. 20. Surface Modification and stability of strong luminescing CdS particles J. Am. Chem. Soc. 1987 109 5649-5666.
42. P. Kamat M. de Lind Van Wijngaarden S. Hotchandani Surface modification of CdS colloids with mercaptoethylamine Isr. J. Chem. 1993 33 47-51.
43. Y. Nosaka M. Fox Effect of charge of polymeric stabilizing agents on the quantum yields of photoinduced electron transfer from photoexcited colloidal semiconductors to adsorbed viologens Langmuir 1987 3 1147-1150.
44. T. Rajh J. Rabani Effects of charged polymers on interfacial electron transfer processes in CdS colloidal systems Langmuir 1991 7 2054-2059.
45. H. Inoue R. Nakamura H. Yoneyama Effect of charged conditions of stabilizers for cadmium sulfide microcrystalline photocatalysts on photoreduction of carbon dioxide Chem. Lett. 1994 1227-1230.
46. U. Resch A. Eychmuller M. Haase H. Weller Absorption and fluorescence behavior of redispersible cadmium sulfide colloids in various organic solvents Langmuir 1992 8 2215-2218.
47. L. Colvin A. Goldstein A. Alivisatos Semiconductor nanocrystals covalently bound to metal surfaces with self-assembled monolayers J. Am. Chem. Soc. 1992 114 5221-5230.
48. P. Kamat N. Dimitrijevic Photoelectrochemistry in semiconductor particulate systems. 13. Surface modification of cadmium sulfide semiconductor colloids with diethyldithiocarbamate J. Phys. Chem. 1989 93 4259-4263.
49. T. Uchihara M. Matsumura J. Ono H. Tsubomura Effect of EDTA on the photocatalytic activities and flatband potentials of cadmium sulfide and cadmium selenide J. Phys. Chem. 1990 94 415-418.
50. R. Rossetti L. Brus Picosecond resonance Raman scattering study of methylviologen reduction on the surface of photoexcited colloidal cadmium sulfide crystallites J. Phys. Chem. 1986 90 558-560.
51. R. Matthews An adsorption water purifier with in situ photocatalytic regeneration J. Catal. 1988 113 549-555.
52. N. Lewis An analysis of charge transfer rate constants for semiconductor/liquid interfaces Annu. Rev. Phys. Chem. 1991 42 543-580.
53. J. Zhang Interfacial charge carrier dynamics of colloidal semiconductor nanoparticles J. Phys. Chem. B 2000 104 7239-7253.
54. D. Amantini F. Pizzo L. Vaccaro Selected methods for the reduction of the azido group Org. Prep. Proced. Int. 2002 34 109-147.
55. M. B. Baizer, Organic Electrochemistry, Marcel Dekker, New York, 1973.
56. Encyclopedia of Electrochemistry of the Elements, ed. P. E. Iversen, Marcel Dekker, New York, 1979, vol. XIII, p. 209.
57. D. Herbranson M. Hawley Electrochemical reduction of p-nitrophenyl azide: evidence consistent with the formation of p-nitrophenylnitrene anion radical as a short-lived intermediate J. Org. Chem. 1990 55 4297-4303.
58. J. Moutet A. Ourari A. Zouaoui Electrocatalytic hydrogenation of azides using precious metal microparticles dispersed in polymer films Electrochim. Acta 1992 37 1261-1263.
59. When methanol is used as a co-solvent for photocatalysis it can act as an electron donor. See ref. 4(c).