Gas-phase azide functionalization of carbon

Journal of the American Chemical Society

Volumn 135, Issue 3, 2013, Pages 1110-1116

  Stenehjem, Eric D ^a   Ziatdinov, Vadim R ^a   Stack, T Daniel P ^a   Chidsey, Christopher E D ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE-ALKYNE CYCLOADDITION; CARBON MATERIAL; CARBON SURFACE; ETHYNYLFERROCENE; FERROCENES; FUNCTIONALIZATIONS; GAS SEPARATIONS; GASEOUS STREAMS; GASPHASE; GLASSY CARBON SURFACES; INTERFACIAL PROPERTY; IODINE MONOCHLORIDE; SIDE REACTIONS; SODIUM AZIDE; TERMINAL ALKYNE; VOLTAMMETRIC; XPS ANALYSIS;

ACETYLENE; CARBON; CATALYSIS; ELECTROCATALYSIS; IODINE; IRON COMPOUNDS; ORGANOMETALLICS; SODIUM; VAPORS; WASTE TREATMENT;

SURFACES;

ALKYNE; AZIDE; CARBON; COPPER; ETHYNYLFERROCENE; FERROCENE; IODINE; IODOAZIDE; SODIUM AZIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CLICK CHEMISTRY; CYCLOADDITION; GAS; HYDROGENATION; POTENTIOMETRY; ULTRAVIOLET SPECTROSCOPY; X RAY PHOTOELECTRON SPECTROSCOPY;

AZIDES; CARBON; GASES; SURFACE PROPERTIES;

EID: 84872804248     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja310410d     Document Type: Article

References (42)

1. Liang, C.; Li, Z.; Dai, S. Angew. Chem., Int. Ed. 2008, 47, 3696-3717
2. McCreery, R. L. Chem Rev 2008, 108, 2646-2687
3. Yang, W.; Auciello, O.; Butler, J. E.; Cai, W.; Carlisle, J. A.; Gerbi, J. E.; Gruen, D. M.; Knickerbocker, T.; Lasseter, T. L.; Russell, J. N.; Smith, L. M.; Hamers, R. J. Nat. Mater. 2002, 1, 253-257
4. Lasseter, T. L.; Clare, B. H.; Abbott, N. L.; Hamers, R. J. J. Am. Chem. Soc. 2004, 126, 10220-10221
5. Downard, A. J. Electroanalysis 2000, 12, 1085-1096
6. Barriere, F.; Downard, A. J. J. Solid State Electrochem. 2008, 12, 1231-1244
7. Pinson, J.; Podvorica, F. Chem. Soc. Rev. 2005, 34, 429-439
8. Nielsen, L. T.; Vase, K. H.; Dong, M.; Besenbacher, F.; Pedersen, S. U.; Daasbjerg, K. J. Am. Chem. Soc. 2007, 129, 1888-1889
9. Combellas, C.; Jiang, D. E.; Kanoufi, F.; Pinson, J.; Podvorica, F. Langmuir 2009, 25, 286-293
10. Leroux, Y. R.; Fei, H.; Noel, J. M.; Roux, C.; Hapiot, P. J. Am. Chem. Soc. 2010, 132, 14039-14041
11. Kongsfelt, M.; Vinther, J.; Malmos, K.; Ceccato, M.; Torbensen, K.; Knudsen, C. S.; Gothelf, K. V.; Pedersen, S. U.; Daasbjerg, K. J. Am. Chem. Soc. 2011, 133, 3788-3791
12. Downard, A. J.; Garrett, D. J.; Tan, E. S. Langmuir 2006, 22, 10739-10746
13. Ssenyange, S.; Anariba, F.; Bocian, D. F.; McCreery, R. L. Langmuir 2005, 21, 11105-11112
14. Sun, B.; Colavita, P. E.; Kim, H.; Lockett, M.; Marcus, M. S.; Smith, L. M.; Hamers, R. J. Langmuir 2006, 22, 9598-9605
15. Yu, S. S.; Downard, A. J. Langmuir 2007, 23, 4662-4668
16. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064
17. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599
18. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021
19. Evans, R. A. Aust. J. Chem. 2007, 60, 384-395
20. Iha, R. K.; Wooley, K. L.; Nystrom, A. M.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Chem. Rev. 2009, 109, 5620-5686
21. McCrory, C. C. L.; Devadoss, A.; Ottenwaelder, X.; Lowe, R. D.; Stack, T. D. P.; Chidsey, C. E. D. J. Am. Chem. Soc. 2011, 133, 3696-3699
22. Devadoss, A.; Chidsey, C. E. D. J. Am. Chem. Soc. 2007, 129, 5370-5371
23. Schulz, A.; Tornieporth-Oetting, I. C.; Klapoetke, T. M. Inorg. Chem. 1995, 34, 4343-4346
24. Engelhardt, U.; Feuerhahn, M.; Minkwitz, R. Z. Anorg. Allg. Chem. 1978, 440, 210-216
25. Tellinghuisen, J. J. Chem. Phys. 1973, 58, 2821-2834
26. Collman, J. P.; Devaraj, N. K.; Eberspacher, T. P. A.; Chidsey, C. E. D. Langmuir 2006, 22, 2457-2464
27. Qu, Z.; Yan, N.; Liu, P.; Jia, J.; Yang, S. J. Hazard. Mater. 2010, 183, 132-137
28. Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications, 2 nd ed.; John Wiley & Sons, Inc.: New York, 2001.
29. Laviron, E. J. Electroanal. Chem. 1979, 101, 19-28
30. Dehnicke, K. Angew. Chem., Int. Ed. 1979, 18, 507-514
31. Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188-5240
32. Hargittai, M.; Molnar, J.; Klapoetke, T. M.; Tornieporth-Oetting, I. C.; Kolonits, M.; Hargittai, I. J. Phys. Chem. 1994, 98, 10095-10097
33. Munz, H. J. Mol. Struct. 2004, 695, 189-202
34. Hassner, A. Acc. Chem. Res. 1971, 4, 9-16
35. Viuf, C.; Bols, M. Angew. Chem., Int. Ed. 2001, 40, 623-625
36. Chidsey, C. E. D.; Bertozzi, C. R.; Putvinski, T. M.; Mujsce, A. M. J. Am. Chem. Soc. 1990, 112, 4301-4306
37. Xia, Y.; Li, W.; Qu, F.; Fan, Z.; Liu, X.; Berro, C.; Rauzy, E.; Peng, L. Org. Biomol. Chem. 2007, 5, 1695-1701
38. Hudlicky, M. Chemistry of Organic Fluorine Compounds: a Laboratory Manual with Comprehensive Literature Coverage, 2 nd ed.; Ellis Horwood: New York, 1992.
39. Zhou, X.; Chang, Y.-C.; Oyama, T.; McGuire, M. J.; Brown, K. C. J. Am. Chem. Soc. 2004, 126, 15656-15657
40. Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853-2855
41. Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193
42. CRC Handbook of Chemistry and Physics, 92 nd ed.; CRC Press: Boca Raton, FL, 2011/2012.