Versatile "click chemistry" Approach to functionalizing silicon quantum dots: Applications toward fluorescent cellular imaging

Langmuir

Volumn 30, Issue 18, 2014, Pages 5209-5216

  Cheng, Xiaoyu ^a,b   Lowe, Stuart B ^a,b   Ciampi, Simone ^a   Magenau, Astrid ^a   Gaus, Katharina ^a,b   Reece, Peter J ^a   Gooding, J Justin ^a,b  

^a UNIVERSITY OF NEW SOUTH WALES   (Australia)

^b UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

QUANTUM DOT; SILICON;

CHEMISTRY; CLICK CHEMISTRY; INFRARED SPECTROSCOPY; PH; PROCEDURES; TEMPERATURE;

CLICK CHEMISTRY; HYDROGEN-ION CONCENTRATION; QUANTUM DOTS; SILICON; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TEMPERATURE;

EID: 84900400658     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la500945f     Document Type: Article

References (50)

1. Alivisatos, A. P. Perspectives on the physical chemistry of semiconductor nanocrystals J. Phys. Chem. 1996, 100 (31) 13226-13239
2. Nirmal, M.; Brus, L. Luminescence photophysics in semiconductor nanocrystals Acc. Chem. Res. 1999, 32 (5) 407-414
3. Strauf, S.; Hennessy, K.; Rakher, M. T.; Choi, Y. S.; Badolato, A.; Andreani, L. C.; Hu, E. L.; Petroff, P. M.; Bouwmeester, D. Self-tuned quantum dot gain in photonic crystal lasers Phys. Rev. Lett. 2006, 96, 12
4. Talapin, D. V.; Lee, J.-S.; Kovalenko, M. V.; Shevchenko, E. V. Prospects of colloidal nanocrystals for electronic and optoelectronic applications Chem. Rev. 2009, 110 (1) 389-458
5. Nozik, A. J. Quantum dot solar cells Phys. E 2002, 14 (1-2) 115-120
6. Michalet, X.; Pinaud, F. F.; Bentolila, L. A.; Tsay, J. M.; Doose, S.; Li, J. J.; Sundaresan, G.; Wu, A. M.; Gambhir, S. S.; Weiss, S. Quantum dots for live cells, in vivo imaging, and diagnostics Science 2005, 307 (5709) 538-544
7. Bruchez, M.; Moronne, M.; Gin, P.; Weiss, S.; Alivisatos, A. P. Semiconductor nanocrystals as fluorescent biological labels Science 1998, 281 (5385) 2013-2016
8. Resch-Genger, U.; Grabolle, M.; Cavaliere-Jaricot, S.; Nitschke, R.; Nann, T. Quantum dots versus organic dyes as fluorescent labels Nat. Methods 2008, 5 (9) 763-775
9. Peng, X.; Manna, L.; Yang, W.; Wickham, J.; Scher, E.; Kadavanich, A.; Alivisatos, A. P. Shape control of CdSe nanocrystals Nature 2000, 404 (6773) 59-61
10. Eychmuller, A.; Rogach, A. L. Chemistry and photophysics of thiol-stabilized II-VI semiconductor nanocrystals Pure Appl. Chem. 2000, 72 (1-2) 179-188
11. Derfus, A. M.; Chan, W. C. W.; Bhatia, S. N. Probing the cytotoxicity of semiconductor quantum dots Nano Lett. 2004, 4 (1) 11-18
12. Erogbogbo, F.; Yong, K. T.; Roy, I.; Hu, R.; Law, W. C.; Zhao, W.; Ding, H.; Wu, F.; Kumar, R.; Swihart, M. T.; Prasad, P. N. In vivo targeted cancer imaging, sentinel lymph node mapping and multi-channel imaging with biocompatible silicon nanocrystals ACS Nano 2011, 5 (1) 413-423
13. Erogbogbo, F.; Yong, K. T.; Roy, I.; Xu, G.; Prasad, P. N.; Swihart, M. T. Biocompatible luminescent silicon quantum dots for imaging of cancer cells ACS Nano 2008, 2 (5) 873-878
14. Erogbogbo, F.; Tien, C. A.; Chang, C. W.; Yong, K. T.; Law, W. C.; Ding, H.; Roy, I.; Swihart, M. T.; Prasad, P. N. Bioconjugation of luminescent silicon quantum dots for selective uptake by cancer cells Bioconjugate Chem. 2011, 22 (6) 1081-1088
15. Shiohara, A.; Prabakar, S.; Faramus, A.; Hsu, C. Y.; Lai, P. S.; Northcote, P. T.; Tilley, R. D. Sized controlled synthesis, purification, and cell studies with silicon quantum dots Nanoscale 2011, 3 (8) 3364-3370
16. He, Y.; Su, Y.; Yang, X.; Kang, Z.; Xu, T.; Zhang, R.; Fan, C.; Lee, S.-T. Photo and pH stable, highly-luminescent silicon nanospheres and their bioconjugates for immunofluorescent cell imaging J. Am. Chem. Soc. 2009, 131 (12) 4434-4438
17. He, Y.; Zhong, Y. L.; Peng, F.; Wei, X. P.; Su, Y. Y.; Lu, Y. M.; Su, S.; Gu, W.; Liao, L. S.; Lee, S. T. One-pot microwave synthesis of water-dispersible, ultraphoto- and pH-stable, and highly fluorescent silicon quantum dots J. Am. Chem. Soc. 2011, 133 (36) 14192-14195
18. Zhong, Y.; Peng, F.; Bao, F.; Wang, S.; Ji, X.; Yang, L.; Su, Y.; Lee, S.-T.; He, Y. Large-scale aqueous synthesis of fluorescent and biocompatible silicon nanoparticles and their use as highly photostable biological probes J. Am. Chem. Soc. 2013, 135 (22) 8350-8356
19. Cheng, X.; Lowe, S. B.; Reece, P. J.; Gooding, J. J. Colloidal silicon quantum dots: from preparation to the modification of self-assembled monolayers (SAMs) for bio-applications Chem. Soc. Rev. 2014, 43 (8) 2680-2700
20. Tilley, R. D.; Yamamoto, K. The microemulsion synthesis of hydrophobic and hydrophilic silicon nanocrystals Adv. Mater. 2006, 18 (15) 2053-2056
21. Warner, J. H.; Hoshino, A.; Yamamoto, K.; Tilley, R. D. Water-soluble photoluminescent silicon quantum dots Angew. Chem., Int. Ed. 2005, 44 (29) 4550-4554
22. Baldwin, R. K.; Pettigrew, K. A.; Ratai, E.; Augustine, M. P.; Kauzlarich, S. M. Solution reduction synthesis of surface stabilized silicon nanoparticles Chem. Commun. 2002, 17, 1822-1823
23. 4 with the Zintl salt, NaSi Chem. Mater. 2001, 13 (3) 765-770
24. Bley, R. A.; Kauzlarich, S. M. A low-temperature solution phase route for the synthesis of silicon nanoclusters J. Am. Chem. Soc. 1996, 118 (49) 12461-12462
25. Yang, C. S.; Bley, R. A.; Kauzlarich, S. M.; Lee, H. W. H.; Delgado, G. R. Synthesis of alkyl-terminated silicon nanoclusters by a solution route J. Am. Chem. Soc. 1999, 121 (22) 5191-5195
26. 2 composites and freestanding hydride-surface-terminated silicon nanoparticles Chem. Mater. 2006, 18 (26) 6139-6146
27. Hessel, C. M.; Henderson, E. J.; Veinot, J. G. C. An investigation of the formation and growth of oxide-embedded silicon nanocrystals in hydrogen silsesquioxane-derived nanocomposites J. Phys. Chem. C 2007, 111 (19) 6956-6961
28. Hua, F.; Swihart, M. T.; Ruckenstein, E. Efficient surface grafting of luminescent silicon quantum dots by photoinitiated hydrosilylation Langmuir 2005, 21 (13) 6054-6062
29. 3 etching Langmuir 2004, 20 (11) 4720-4727
30. He, Y.; Kang, Z.-H.; Li, Q.-S.; Tsang, C. H. A.; Fan, C.-H.; Lee, S.-T. Ultrastable, highly fluorescent, and water-dispersed silicon-based nanospheres as cellular probes Angew. Chem., Int. Ed. 2009, 48 (1) 128-132
31. Kang, Z.; Tsang, C. H. A.; Zhang, Z.; Zhang, M.; Wong, N.-b.; Zapien, J. A.; Shan, Y.; Lee, S.-T. A polyoxometalate-assisted electrochemical method for silicon nanostructures preparation: From quantum dots to nanowires J. Am. Chem. Soc. 2007, 129 (17) 5326-5327
32. Kang, Z. H.; Tsang, C. H. A.; Wong, N. B.; Zhang, Z. D.; Lee, S. T. Silicon quantum dots: A general photocatalyst for reduction, decomposition, and selective oxidation reactions J. Am. Chem. Soc. 2007, 129 (40) 12090-12091
33. Mangolini, L.; Kortshagen, U. Plasma-assisted synthesis of silicon nanocrystal inks Adv. Mater. 2007, 19 (18) 2513-2519
34. Jurbergs, D.; Rogojina, E.; Mangolini, L.; Kortshagen, U. Silicon nanocrystals with ensemble quantum yields exceeding 60% Appl. Phys. Lett. 2006, 88, 23
35. Mangolini, L.; Thimsen, E.; Kortshagen, U. High-yield plasma synthesis of luminescent silicon nanocrystals Nano Lett. 2005, 5 (4) 655-659
36. Kelly, J. A.; Veinot, J. G. C. An investigation into near-UV hydrosilylation of freestanding silicon nanocrystals ACS Nano 2010, 4 (8) 4645-4656
37. Kelly, J. A.; Shukaliak, A. M.; Fleischauer, M. D.; Veinot, J. G. C. Size-dependent reactivity in hydrosilylation of silicon nanocrystals J. Am. Chem. Soc. 2011, 133 (24) 9564-9571
38. Shiohara, A.; Hanada, S.; Prabakar, S.; Fujioka, K.; Lim, T. H.; Yamamoto, K.; Northcote, P. T.; Tilley, R. D. Chemical reactions on surface molecules attached to silicon quantum dots J. Am. Chem. Soc. 2010, 132 (1) 248-253
39. Ruizendaal, L.; Pujari, S. P.; Gevaerts, V.; Paulusse, J. M.; Zuilhof, H. Biofunctional silicon nanoparticles by means of thiol-ene click chemistry Chem.-Asian J. 2011, 6 (10) 2776-2786
40. Cheng, X. Y.; Gondosiswanto, R.; Ciampi, S.; Reece, P. J.; Gooding, J. J. One-pot synthesis of colloidal silicon quantum dots and surface functionalization via thiol-ene click chemistry Chem. Commun. 2012, 48 (97) 11874-11876
41. Biesta, W.; van Lagen, B.; Gevaert, V. S.; Marcelis, A. T. M.; Paulusse, J. M. J.; Nielen, M. W. F.; Zuilhof, H. Preparation, characterization, and surface modification of trifluoroethyl ester-terminated silicon nanoparticles Chem. Mater. 2012, 24 (22) 4311-4318
42. Warner, J. H.; Hoshino, A.; Yamamoto, K.; Tilley, R. D. Water-soluble photoluminescent silicon quantum dots Angew. Chem., Int. Ed. 2005, 44 (29) 4550-4554
43. Tilley, R. D.; Warner, J. H.; Yamamoto, K.; Matsui, I.; Fujimori, H. Micro-emulsion synthesis of monodisperse surface stabilized silicon nanocrystals Chem. Commun. 2005, 0 (14) 1833-1835
44. Shiohara, A.; Hanada, S.; Prabakar, S.; Fujioka, K.; Lim, T. H.; Yamamoto, K.; Northcote, P. T.; Tilley, R. D. Chemical reactions on surface molecules attached to silicon quantum dots J. Am. Chem. Soc. 2010, 132 (1) 248-253
45. Pandey, P.; Farha, O. K.; Spokoyny, A. M.; Mirkin, C. A.; Kanatzidis, M. G.; Hupp, J. T.; Nguyen, S. T. A "click-based" porous organic polymer from tetrahedral building blocks J. Mater. Chem. 2011, 21 (6) 1700-1703
46. Yin, Y.; Alivisatos, A. P. Colloidal nanocrystal synthesis and the organic-inorganic interface Nature 2005, 437 (7059) 664-670
47. Baldwin, R. K.; Pettigrew, K. A.; Garno, J. C.; Power, P. P.; Liu, G. Y.; Kauzlarich, S. M. Room temperature solution synthesis of alkyl-capped tetrahedral shaped silicon nanocrystals J. Am. Chem. Soc. 2002, 124 (7) 1150-1151
48. Dasog, M.; Yang, Z.; Regli, S.; Atkins, T. M.; Faramus, A.; Singh, M. P.; Muthuswamy, E.; Kauzlarich, S. M.; Tilley, R. D.; Veinot, J. G. C. Chemical insight into the origin of red and blue photoluminescence arising from freestanding silicon nanocrystals ACS Nano 2013, 7 (3) 2676-2685
49. Mastronardi, M. L.; Henderson, E. J.; Puzzo, D. P.; Ozin, G. A. Small silicon, big opportunities: The development and future of colloidally-stable monodisperse silicon nanocrystals Adv. Mater. 2012, 24 (43) 5890-5898
50. Gao, X. H.; Yang, L. L.; Petros, J. A.; Marshal, F. F.; Simons, J. W.; Nie, S. M. In vivo molecular and cellular imaging with quantum dots Curr. Opin. Biotechnol. 2005, 16 (1) 63-72