Covalent functionalization and passivation of exfoliated black phosphorus via aryl diazonium chemistry

Nature Chemistry

Volumn 8, Issue 6, 2016, Pages 597-602

  Ryder, Christopher R ^a   Wood, Joshua D ^a   Wells, Spencer A ^a   Yang, Yang ^b   Jariwala, Deep ^a   Marks, Tobin J ^a   Schatz, George C ^a   Hersam, Mark C ^a  

^a Northwestern University   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84971280972     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.2505     Document Type: Article

References (45)

1. Morita, A. Semiconducting black phosphorus. Appl. Phys. A 39, 227-242 (1986).
2. Tran, V., Soklaski, R., Liang, Y. & Yang, L. Layer-controlled band gap and anisotropic excitons in few-layer black phosphorus. Phys. Rev. B 89, 235319 (2014).
3. Ling, X., Wang, H., Huang, S., Xia, F. & Dresselhaus, M. S. The renaissance of black phosphorus. Proc. Natl Acad. Sci. USA 112, 4523-4530 (2015).
4. Kou, L., Chen, C. & Smith, S. C. Phosphorene: fabrication, properties, and applications. J. Phys. Chem. Lett. 6, 2794-2805 (2015).
5. Das, S. et al. Tunable transport gap in phosphorene. Nano Lett. 14, 5733-5739 (2014).
6. Liu, H. et al. Phosphorene: an unexplored 2D semiconductor with a high hole mobility. ACS Nano 8, 4033-4041 (2014).
7. Li, L. et al. Black phosphorus field-effect transistors. Nature Nanotech. 9, 372-377 (2014).
8. Wang, H. et al. Black phosphorus radio-frequency transistors. Nano Lett. 14, 6424-6429 (2014).
9. Koenig, S. P., Doganov, R. A., Schmidt, H., Neto, A. C. & Oezyilmaz, B. Electric field effect in ultrathin black phosphorus. Appl. Phys. Lett. 104, 103106 (2014).
10. Wang, Q. H., Kalantar-Zadeh, K., Kis, A., Coleman, J. N. & Strano, M. S. Electronics and optoelectronics of two-dimensional transition metal dichalcogenides. Nature Nanotech. 7, 699-712 (2012).
11. Jariwala, D., Sangwan, V. K., Lauhon, L. J., Marks, T. J. & Hersam, M. C. Emerging device applications for semiconducting two-dimensional transition metal dichalcogenides. ACS Nano 8, 1102-1120 (2014).
12. Xia, F., Wang, H. & Jia, Y. Rediscovering black phosphorus as an anisotropic layered material for optoelectronics and electronics. Nature Commun. 5, 4458 (2014).
13. Buscema, M. et al. Fast and broadband photoresponse of few-layer black phosphorus field-effect transistors. Nano Lett. 14, 3347-3352 (2014).
14. Low, T., Engel, M., Steiner, M. & Avouris, P. Origin of photoresponse in black phosphorus phototransistors. Phys. Rev. B 90, 081408 (2014).
15. Sun, J. et al. Formation of stable phosphorus-carbon bond for enhanced performance in black phosphorus nanoparticle-graphite composite battery anodes. Nano Lett. 14, 4573-4580 (2014).
16. Kou, L., Frauenheim, T. & Chen, C. Phosphorene as a superior gas sensor: selective adsorption and distinct I-V response. J. Phys. Chem. Lett. 5, 2675-2681 (2014).
17. Wood, J. D. et al. Effective passivation of exfoliated black phosphorus transistors against ambient degradation. Nano Lett. 14, 6964-6970 (2014).
18. Favron, A. et al. Photooxidation and quantum confinement effects in exfoliated black phosphorus. Nature Mater. 14, 826-832 (2015).
19. Goldwhite, H. Introduction to Phosphorus Chemistry (Cambridge Univ. Press, 1981).
20. Dreyer, D. R., Park, S., Bielawski, C. W. & Ruoff, R. S. The chemistry of graphene oxide. Chem. Soc. Rev. 39, 228-240 (2010).
21. Johns, J. E. et al. Metal oxide nanoparticle growth on graphene via chemical activation with atomic oxygen. J. Am. Chem. Soc. 135, 18121-18125 (2013).
22. Loh, K. P., Bao, Q., Eda, G. & Chhowalla, M. Graphene oxide as a chemically tunable platform for optical applications. Nature Chem. 2, 1015-1024 (2010).
23. Johns, J. E. & Hersam, M. C. Atomic covalent functionalization of graphene. Accounts Chem. Res. 46, 77-86 (2012).
24. Voiry, D. et al. Covalent functionalization of monolayered transition metal dichalcogenides by phase engineering. Nature Chem. 45-49 (2014).
25. Delamar, M., Hitmi, R., Pinson, J. & Saveant, J. M. Covalent modification of carbon surfaces by grafting of functionalized aryl radicals produced from electrochemical reduction of diazonium salts. J. Am. Chem. Soc. 114, 5883-5884 (1992).
26. Kariuki, J. K. & McDermott, M. T. Nucleation and growth of functionalized aryl films on graphite electrodes. Langmuir 15, 6534-6540 (1999).
27. 3 defects. Nature Chem. 5, 840-845 (2013).
28. Niyogi, S. et al. Spectroscopy of covalently functionalized graphene. Nano Lett. 10, 4061-4066 (2010).
29. Englert, J. M. et al. Covalent bulk functionalization of graphene. Nature Chem. 3, 279-286 (2011).
30. Bahr, J. L. et al. Functionalization of carbon nanotubes by electrochemical reduction of aryl diazonium salts: a bucky paper electrode. J. Am. Chem. Soc. 123, 6536-6542 (2001).
31. Wang, Q. H. et al. Understanding and controlling the substrate effect on graphene electron-transfer chemistry via reactivity imprint lithography. Nature Chem. 4, 724-732 (2012).
32. Bekyarova, E. et al. Chemical modification of epitaxial graphene: spontaneous grafting of aryl groups. J. Am. Chem. Soc. 131, 1336-1337 (2009).
33. Koehler, F. M., Jacobsen, A., Ensslin, K., Stampfer, C. & Stark, W. J. Selective chemical modification of graphene surfaces: distinction between single-and bilayer graphene. Small 6, 1125-1130 (2010).
34. Pelavin, M., Hendrickson, D., Hollander, J. & Jolly, W. Phosphorus 2p electron binding energies. Correlation with extended Hueckel charges. J. Phys. Chem. 74, 1116-1121 (1970).
35. Blackburn, J. R., Nordberg, R., Stevie, F., Albridge, R. G. & Jones, M. M. Photoelectron spectroscopy of coordination compounds. Triphenylphosphine and its complexes. Inorg. Chem. 9, 2374-2376 (1970).
36. Sugai, S. & Shirotani, I. Raman and infrared reflection spectroscopy in black phosphorus. Solid State Commun. 53, 753-755 (1985).
37. Zhang, S. et al. Extraordinary photoluminescence and strong temperature/angle-dependent Raman responses in few-layer phosphorene. ACS Nano 8, 9590-9596 (2014).
38. Allongue, P. et al. Covalent modification of carbon surfaces by aryl radicals generated from the electrochemical reduction of diazonium salts. J. Am. Chem. Soc. 119, 201-207 (1997).
39. Paulus, G. L., Wang, Q. H. & Strano, M. S. Covalent electron transfer chemistry of graphene with diazonium salts. Acc. Chem. Res. 46, 160-170 (2012).
40. Hansch, C., Leo, A. & Taft, R. A survey of Hammett substituent constants and resonance and field parameters. Chem. Rev. 91, 165-195 (1991).
41. Elofson, R. M. & Gadallah, F. Substituent effects in the polarography of aromatic diazonium salts. J. Org. Chem. 34, 854-857 (1969).
42. Farmer, D. B. et al. Chemical doping and electron-hole conduction asymmetry in graphene devices. Nano Lett. 9, 388-392 (2008).
43. Coletti, C. et al. Charge neutrality and band-gap tuning of epitaxial graphene on SiC by molecular doping. Phys. Rev. B 81, 235401 (2010).
44. Sinitskii, A. et al. Kinetics of diazonium functionalization of chemically converted graphene nanoribbons. ACS Nano 4, 1949-1954 (2010).
45. Xiang, D. et al. Surface transfer doping induced effective modulation on ambipolar characteristics of few-layer black phosphorus. Nature Commun. 6, 6485 (2015).