Fluorescence probing of thiol-functionalized gold nanoparticles: Is alkylthiol coating of a nanoparticle as hydrophobic as expected?

Journal of Physical Chemistry C

Volumn 116, Issue 39, 2012, Pages 21059-21068

  Kyrychenko, Alexander ^a,b,c   Karpushina, Galina V ^a   Svechkarev, Denis ^a   Kolodezny, Dmitry ^a   Bogatyrenko, Sergey I ^a   Kryshtal, Alexander P ^a   Doroshenko, Andrey O ^a,b,c  

^a V N KARAZIN KHARKIV NATIONAL UNIVERSITY   (Ukraine)

^b Ukrainian American Laboratory of Computational Chemistry   (Ukraine)

^c Ukrainian American Laboratory of Computational Chemistry   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AVERAGE DIAMETER; CLOSE PROXIMITY; DODECANETHIOL MONOLAYERS; DODECANETHIOLS; DUAL BAND; EMISSION BANDS; EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER; FLUORESCENCE LIFETIMES; FLUORESCENCE PROBING; FLUORESCENCE QUENCHING; FLUORESCENCE TITRATIONS; FLUORESCENT DYES; FLUORESCENT LABELING AGENT; FLUORESCENT PROBES; FORCE FIELD PARAMETERS; GOLD NANOPARTICLES; INTENSITY RATIO; INTERMOLECULAR HYDROGEN BONDING; LIGAND SHELLS; MD SIMULATION; METAL SURFACES; MICROENVIRONMENTS; MOLECULAR DYNAMICS SIMULATIONS; MOLECULAR SENSORS; MONOLAYER-PROTECTED GOLD NANOPARTICLES; NMR SPECTRUM; NONCOVALENT; OUTER SHELLS; PROBE MOLECULES; RATIOMETRIC FLUORESCENCE; SMALL POPULATION; STRUCTURAL FEATURE; SUPRAMOLECULAR LEVEL; TOLUENE SOLUTION; TRANSMISSION ELECTRON MICROGRAPH;

COMPLEXATION; ETHANOL; FLUORESCENCE; GOLD; HYDROGEN BONDS; HYDROPHOBICITY; LIGANDS; METAL NANOPARTICLES; MOLECULAR DYNAMICS; MOLECULES; MONOLAYERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROBES; SHELLS (STRUCTURES); SPECTRUM ANALYSIS; SYNTHESIS (CHEMICAL); TOLUENE;

FLUOROPHORES;

EID: 84867186711     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp3060813     Document Type: Article

References (43)

1. de Dios, A. S.; Díaz-García, M. E. Multifunctional nanoparticles: analytical prospects Anal. Chim. Acta 2010, 666 (1-2) 1-22
2. Martin, M. N.; Basham, J. I.; Chando, P.; Eah, S.-K. Charged gold nanoparticles in non-polar solvents: 10-min synthesis and 2D self-assembly Langmuir 2010, 26 (10) 7410-7417
3. Boal, A. K.; Rotello, V. M. Fabrication and self-optimization of multivalent receptors on nanoparticle scaffolds J. Am. Chem. Soc. 2000, 122 (4) 734-735
4. Maggini, L.; Bonifazi, D. Hierarchised luminescent organic architectures: design, synthesis, self-assembly, self-organisation and functions Chem. Soc. Rev. 2012, 41 (1) 211-241
5. Thomas, K. G.; Kamat, P. V. Making gold nanoparticles glow: enhanced emission from a surface-bound fluoroprobe J. Am. Chem. Soc. 2000, 122 (11) 2655-2656
6. Shi, X.; Wang, S. H.; Van Antwerp, M. E.; Chen, X.; Baker, J. J. R. Targeting and detecting cancer cells using spontaneously formed multifunctional dendrimer-stabilized gold nanoparticles Analyst 2009, 134 (7) 1373-1379
7. Zheng, H.; Li, Y.; Liu, H.; Yin, X.; Li, Y. Construction of heterostructure materials toward functionality Chem. Soc. Rev. 2011, 40 (9) 4506-4524
8. Yu, M.; Zhou, C.; Liu, J.; Hankins, J. D.; Zheng, J. Luminescent gold nanoparticles with pH-dependent membrane adsorption J. Am. Chem. Soc. 2011, 133 (29) 11014-11017
9. Chen, J.; Zheng, A.; Chen, A.; Gao, Y.; He, C.; Kai, X.; Wu, G.; Chen, Y. A functionalized gold nanoparticles and rhodamine 6G based fluorescent sensor for high sensitive and selective detection of mercury(II) in environmental water samples Anal. Chim. Acta 2007, 599 (1) 134-142
10. 2+) in aqueous media using chemodosimeter-functionalized gold nanoparticles Sens. Actuators, B 2009, 140 (1) 162-169
11. Velu, R.; Ramakrishnan, V. T.; Ramamurthy, P. Selective fluoride ion recognition by a thiourea based receptor linked acridinedione functionalized gold nanoparticles J. Photochem. Photobiol., A 2011, 217 (2-3) 313-320
12. Tian, P. Molecular dynamics simulations of nanoparticles Annual Reports Section ''C'' (Physical Chemistry) 2008, 104, 142-164
13. Jiménez, A.; Sarsa, A.; Blázquez, M.; Pineda, T. A molecular dynamics study of the surfactant surface density of alkanethiol self-assembled monolayers on gold nanoparticles as a function of the radius J. Phys. Chem. C 2010, 114 (49) 21309-21314
14. Kyrychenko, A.; Karpushina, G. V.; Bogatyrenko, S. I.; Kryshtal, A. P.; Doroshenko, A. O. Preparation, structure, and a coarse-grained molecular dynamics model for dodecanethiol-stabilized gold nanoparticles Comput. Theor. Chem. 2011, 977 (1-3) 34-39
15. Kumar, S.; Jain, S. K.; Sharma, N.; Rastogi, R. C. Intramolecular excited-state proton-transfer studies on flavones in different environments Spectrochim. Acta, Part A 2001, 57 (2) 299-308
16. Woolfe, G. J.; Thistlethwaite, P. J. Direct observation of excited state intramolecular proton transfer kinetics in 3-hydroxyflavone J. Am. Chem. Soc. 1981, 103 (23) 6916-6923
17. Valuk, V. F.; Duportail, G.; Pivovarenko, V. G. A wide-range fluorescent pH-indicator based on 3-hydroxyflavone structure J. Photochem. Photobiol., A 2005, 175 (2-3) 226-231
18. 2+ complexes J. Phys. Chem. A 1998, 102 (29) 5907-5914
19. Duportail, G.; Klymchenko, A.; Mely, Y.; Demchenko, A. Neutral fluorescence probe with strong ratiometric response to surface charge of phospholipid membranes FEBS Lett. 2001, 508 (2) 196-200
20. Demchenko, A. P.; Mély, Y.; Duportail, G.; Klymchenko, A. S. Monitoring biophysical properties of lipid membranes by environment-sensitive fluorescent probes Biophys. J. 2009, 96 (9) 3461-3470
21. Klymchenko, A. S.; Shvadchak, V. V.; Yushchenko, D. A.; Jain, N.; Mély, Y. Excited-state intramolecular proton transfer distinguishes microenvironments in single- and double-stranded DNA J. Phys. Chem. B 2008, 112 (38) 12050-12055
22. Svechkarev, D. A.; Baumer, V. N.; Syzova, Z. A.; Doroshenko, A. O. New benzimidazolic 3-hydroxychromone derivative with two alternative mechanisms of the excited state intramolecular proton transfer reaction J. Mol. Struct. 2008, 882 (1-3) 63-69
23. 2+ probing J. Phys. Chem. A 2011, 115 (17) 4223-4230
24. Svechkarev, D.; Karpushina, G.; Lukatskaya, L.; Doroshenko, A. 2-(Benzimidazol-2-yl)-3-hydroxychromone derivatives: spectroscopic properties and a possibile alternative intramolecular proton phototransfer Cent. Eur. J. Chem. 2008, 6 (3) 443-449
25. Angelova, P.; Kuchukova, N.; Dobrikov, G. M.; Timtcheva, I.; Kostova, K.; Petkova, I.; Vauthey, E. Fluorescent monolayer protected gold nanoparticles - preparation and structure elucidation J. Mol. Struct. 2011, 993 (1-3) 185-192
26. Brust, M.; Walker, M.; Bethell, D.; Schiffrin, D. J.; Whyman, R. Synthesis of thiol-derivatised gold nanoparticles in a two-phase liquid-liquid system J. Chem. Soc., Chem. Commun. 1994, 7, 801-802
27. MacKerell, A. D.; Banavali, N.; Foloppe, N. Development and current status of the CHARMM force field for nucleic acids Biopolymers 2001, 56 (4) 257-265
28. Bjelkmar, P. R.; Larsson, P.; Cuendet, M. A.; Hess, B.; Lindahl, E. Implementation of the CHARMM force field in GROMACS: analysis of protein stability effects from correction maps, virtual interaction sites, and water models J. Chem. Theory Comput. 2010, 6 (2) 459-466
29. Zoete, V.; Cuendet, M. A.; Grosdidier, A.; Michielin, O. SwissParam: a fast force field generation tool for small organic molecules J. Comput. Chem. 2011, 32 (11) 2359-2368
30. Jadzinsky, P. D.; Calero, G.; Ackerson, C. J.; Bushnell, D. A.; Kornberg, R. D. Structure of a thiol monolayer-protected gold nanoparticle at 1.1 Å resolution Science 2007, 318 (5849) 430-433
31. Van Der Spoel, D.; Lindahl, E.; Hess, B.; Groenhof, G.; Mark, A. E.; Berendsen, H. J. C. GROMACS: fast, flexible, and free J. Comput. Chem. 2005, 26 (16) 1701-1718
32. Hess, B. P-LINCS: a parallel linear constraint solver for molecular simulation J. Chem. Theory Comput. 2007, 4 (1) 116-122
33. Essmann, U.; Perera, L.; Berkowitz, M. L.; Darden, T.; Lee, H.; Pedersen, L. G. A smooth particle mesh Ewald method J. Chem. Phys. 1995, 103 (19) 8577-8593
34. Bussi, G.; Donadio, D.; Parrinello, M. Canonical sampling through velocity rescaling J. Chem. Phys. 2007, 126 (1) 014101-1-014101-7
35. Parrinello, M.; Rahman, A. Polymorphic transitions in single crystals: a new molecular dynamics method J. Appl. Phys. 1981, 52 (12) 7182-7190
36. Humphrey, W.; Dalke, A.; Schulten, K. VMD: visual molecular dynamics J. Mol. Graphics 1996, 14 (1) 33-38
37. Tournebize, J.; Sapin-Minet, A.; Schneider, R.; Boudier, A.; Maincent, P.; Leroy, P. Simple spectrophotocolorimetric method for quantitative determination of gold in nanoparticles Talanta 2011, 83 (5) 1780-1783
38. Seelig, J.; Leslie, K.; Renn, A.; Kühn, S.; Jacobsen, V.; van de Corput, M.; Wyman, C.; Sandoghdar, V. Nanoparticle-induced fluorescence lifetime modification as nanoscopic ruler: demonstration at the single molecule level Nano Lett. 2007, 7 (3) 685-689
39. McMorrow, D.; Kasha, M. Intramolecular excited-state proton transfer in 3-hydroxyflavone. Hydrogen-bonding solvent perturbations J. Phys. Chem. 1984, 88 (11) 2235-2243
40. Shynkar, V. V.; Klymchenko, A. S.; Piémont, E.; Demchenko, A. P.; Mély, Y. Dynamics of intermolecular hydrogen bonds in the excited states of 4′-dialkylamino-3-hydroxyflavones. On the pathway to an ideal fluorescent hydrogen bonding sensor J. Phys. Chem. A 2004, 108 (40) 8151-8159
41. Svechkarev, D. A.; Bukatich, I. V.; Doroshenko, A. O. New 1,3,5-triphenyl-2-pyrazoline-containing 3-hydroxychromones as highly solvatofluorochromic ratiometric polarity probes J. Photochem. Photobiol., A 2008, 200 (2-3) 426-431
42. Kyrychenko, A.; Sevriukov, I. Y.; Syzova, Z. A.; Ladokhin, A. S.; Doroshenko, A. O. Partitioning of 2,6-bis(1H-benzimidazol-2-yl)pyridine fluorophore into a phospholipid bilayer: complementary use of fluorescence quenching studies and molecular dynamics simulations Biophys. Chem. 2011, 154 (1) 8-17
43. Kyrychenko, A.; Wu, F.; Thummel, R. P.; Waluk, J.; Ladokhin, A. S. Partitioning and localization of environment-sensitive 2-(2′-pyridyl)- and 2-(2′-pyrimidyl)-indoles in lipid membranes: a joint refinement using fluorescence measurements and molecular dynamics simulations J. Phys. Chem. B 2010, 114 (42) 13574-13584