Description of the Adsorption and Exciton Delocalizing Properties of p-Substituted Thiophenols on CdSe Quantum Dots

Langmuir

Volumn 32, Issue 14, 2016, Pages 3354-3364

  Aruda, Kenneth O ^a   Amin, Victor A ^a   Thompson, Christopher M ^a   Lau, Bryan ^a   Nepomnyashchii, Alexander B ^a   Weiss, Emily A ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; BINS; CHLORINE; ELECTRONIC STRUCTURE; EXCITONS; MIXTURES; NANOCRYSTALS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CDSE QUANTUM DOTS; ELECTRONWITHDRAWING; EXCITON DELOCALIZATION; INTERFACIAL CHEMICALS; INTERFACIAL REGION; P-SUBSTITUTED THIOPHENOLS; POTENTIAL BARRIERS; QUANTITATIVE CHARACTERIZATION;

SEMICONDUCTOR QUANTUM DOTS;

EID: 84964497479     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/acs.langmuir.6b00689     Document Type: Article

References (51)

1. Frederick, M. T.; Amin, V. A.; Swenson, N. K.; Ho, A. Y.; Weiss, E. A. Control of Exciton Confinement in Quantum Dot-Organic Complexes through Energetic Alignment of Interfacial Orbitals Nano Lett. 2013, 13, 287-292 10.1021/nl304098e
2. Jin, S.; Harris, R. D.; Lau, B.; Aruda, K. O.; Amin, V. A.; Weiss, E. A. Enhanced Rate of Radiative Decay in CdSe Quantum Dots Upon Adsorption of an Exciton-Delocalizing Ligand Nano Lett. 2014, 14, 5323-5328 10.1021/nl5023699
3. Wuister, S. F.; de Mello Donegá, C.; Meijerink, A. Influence of Thiol Capping on the Exciton Luminescence and Decay Kinetics of Cdte and CdSe Quantum Dots J. Phys. Chem. B 2004, 108, 17393-17397 10.1021/jp047078c
4. Konstantatos, G.; Howard, I.; Fischer, A.; Hoogland, S.; Clifford, J.; Klem, E.; Levina, L.; Sargent, E. H. Ultrasensitive Solution-Cast Quantum Dot Photodetectors Nature 2006, 442, 180-183 10.1038/nature04855
5. Talapin, D. V.; Shevchenko, E. V.; Kornowski, A.; Gaponik, N.; Haase, M.; Rogach, A. L.; Weller, H. A New Approach to Crystallization of CdSe Nanoparticles into Ordered Three-Dimensional Superlattices Adv. Mater. 2001, 13, 1868-1871 10.1002/1521-4095(200112)13:24<1868::AID-ADMA1868>3.0.CO;2-0
6. Jarosz, M. V.; Porter, V. J.; Fisher, B. R.; Kastner, M. A.; Bawendi, M. G. Photoconductivity Studies of Treated CdSe Quantum Dot Films Exhibiting Increased Exciton Ionization Efficiency Phys. Rev. B: Condens. Matter Mater. Phys. 2004, 70, 195327 10.1103/PhysRevB.70.195327
7. Matylitsky, V. V.; Dworak, L.; Breus, V. V.; Basche, T.; Wachtveitl, J. Ultrafast Charge Separation in Multiexcited CdSe Quantum Dots Mediated by Adsorbed Electron Acceptors J. Am. Chem. Soc. 2009, 131, 2424-2425 10.1021/ja808084y
8. Tyagi, P. Multilayer Edge Molecular Electronics Devices: A Review J. Mater. Chem. 2011, 21, 4733-4742 10.1039/c0jm03291c
9. Ji, M.; Park, S.; Connor, S. T.; Mokari, T.; Cui, Y.; Gaffney, K. J. Efficient Multiple Exciton Generation Observed in Colloidal PbSe Quantum Dots with Temporally and Spectrally Resolved Intraband Excitation Nano Lett. 2009, 9, 1217-1222 10.1021/nl900103f
10. Hines, D. A.; Kamat, P. V. Quantum Dot Surface Chemistry: Ligand Effects and Electron Transfer Reactions J. Phys. Chem. C 2013, 117, 14418-14426 10.1021/jp404031s
11. Xie, Y.; Teunis, M. B.; Pandit, B.; Sardar, R.; Liu, J. Molecule-Like CdSe Nanoclusters Passivated with Strongly Interacting Ligands: Energy Level Alignment and Photoinduced Ultrafast Charge Transfer Processes J. Phys. Chem. C 2015, 119, 2813-2821 10.1021/jp510276c
12. Amin, V. A.; Aruda, K. O.; Lau, B.; Rasmussen, A. M.; Edme, K.; Weiss, E. A. The Dependence of the Bandgap of CdSe Quantum Dots on the Surface Coverage and Binding Mode of an Exciton-Delocalizing Ligand, Methylthiophenolate J. Phys. Chem. C 2015, 119, 19423-19429 10.1021/acs.jpcc.5b04306
13. Yu, W. W.; Qu, L. H.; Guo, W. Z.; Peng, X. G. Experimental Determination of the Extinction Coefficient of CdTe, CdSe, and CdS Nanocrystals Chem. Mater. 2003, 15, 2854-2860 10.1021/cm034081k
14. Shao, Y. et al. Advances in Methods and Algorithms in a Modern Quantum Chemistry Program Package Phys. Chem. Chem. Phys. 2006, 8, 3172-3191 10.1039/B517914A
15. Zhao, Y.; Truhlar, D. G. The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-Class Functionals and 12 Other Functionals Theor. Chem. Acc. 2008, 120, 215-241 10.1007/s00214-007-0310-x
16. Weigend, F.; Ahlrichs, R. Balanced Basis Sets of Split Valence, Triple Zeta Valence and Quadruple Zeta Valence Quality for H to Rn: Design and Assessment of Accuracy Phys. Chem. Chem. Phys. 2005, 7, 3297-3305 10.1039/b508541a
17. Wheeler, S. E.; Houk, K. N. Integration Grid Errors for Meta-Gga-Predicted Reaction Energies: Origin of Grid Errors for the M06 Suite of Functionals J. Chem. Theory Comput. 2010, 6, 395-404 10.1021/ct900639j
18. Schäfer, A.; Klamt, A.; Sattel, D.; Lohrenz, J. C.; Eckert, F. Cosmo Implementation in Turbomole: Extension of an Efficient Quantum Chemical Code Towards Liquid Systems Phys. Chem. Chem. Phys. 2000, 2, 2187-2193 10.1039/b000184h
19. Sahami, S.; Weaver, M. J. Entropic and Enthalpic Contributions to the Solvent Dependence of the Thermodynamics of Transition-Metal Redox Couples J. Electroanal. Chem. Interfacial Electrochem. 1981, 122, 155-170 10.1016/S0022-0728(81)80147-7
20. Morris-Cohen, A. J.; Donakowski, M. D.; Knowles, K. E.; Weiss, E. A. The Effect of a Common Purification Procedure on the Chemical Composition of the Surfaces of CdSe Quantum Dots Synthesized with Trioctylphosphine Oxide J. Phys. Chem. C 2010, 114, 897-906 10.1021/jp909492w
21. Morris-Cohen, A. J.; Frederick, M. T.; Lilly, G. D.; McArthur, E. A.; Weiss, E. A. Organic Surfactant-Controlled Composition of the Surfaces of CdSe Quantum Dots J. Phys. Chem. Lett. 2010, 1, 1078-1081 10.1021/jz100224q
22. Cass, L. C.; Swenson, N. K.; Weiss, E. A. Electronic and Vibrational Structure of Complexes of Tetracyanoquinodimethane with Cadmium Chalcogenide Quantum Dots J. Phys. Chem. C 2014, 118, 18263-18270 10.1021/jp505986c
23. Buckley, J. J.; Couderc, E.; Greaney, M. J.; Munteanu, J.; Riche, C. T.; Bradforth, S. E.; Brutchey, R. L. Chalcogenol Ligand Toolbox for CdSe Nanocrystals and Their Influence on Exciton Relaxation Pathways ACS Nano 2014, 8, 2512-2521 10.1021/nn406109v
24. Harris, R. D.; Amin, V. A.; Lau, B.; Weiss, E. A. The Role of Inter-Ligand Coupling in Determining the Interfacial Electronic Structure of Colloidal CdS Quantum Dots ACS Nano 2016, 10, 1395-1403 10.1021/acsnano.5b06837
25. Badia, A.; Gao, W.; Singh, S.; Demers, L.; Cuccia, L.; Reven, L. Structure and Chain Dynamics of Alkanethiol-Capped Gold Colloids Langmuir 1996, 12, 1262-1269 10.1021/la9510487
26. Badia, A.; Lennox, R. B.; Reven, L. A Dynamic View of Self-Assembled Monolayers Acc. Chem. Res. 2000, 33, 475-481 10.1021/ar9702841
27. Hassinen, A.; Moreels, I.; De Nolf, K.; Smet, P. F.; Martins, J. C.; Hens, Z. Short-Chain Alcohols Strip X-Type Ligands and Quench the Luminescence of PbSe and CdSe Quantum Dots, Acetonitrile Does Not J. Am. Chem. Soc. 2012, 134, 20705-20712 10.1021/ja308861d
28. Hens, Z.; Martins, J. C. A Solution Nmr Toolbox for Characterizing the Surface Chemistry of Colloidal Nanocrystals Chem. Mater. 2013, 25, 1211-1221 10.1021/cm303361s
29. Hostetler, M. J. et al. Alkanethiolate Gold Cluster Molecules with Core Diameters from 1.5 to 5.2 nm: Core and Monolayer Properties as a Function of Core Size Langmuir 1998, 14, 17-30 10.1021/la970588w
30. Kohlmann, O.; Steinmetz, W. E.; Mao, X.-A.; Wuelfing, W. P.; Templeton, A. C.; Murray, R. W.; Johnson, C. S. Nmr Diffusion, Relaxation, and Spectroscopic Studies of Water Soluble, Monolayer-Protected Gold Nanoclusters J. Phys. Chem. B 2001, 105, 8801-8809 10.1021/jp011123o
31. Liu, X.; Yu, M.; Kim, H.; Mameli, M.; Stellacci, F. Determination of Monolayer-Protected Gold Nanoparticle Ligand-Shell Morphology Using NMR Nat. Commun. 2012, 3, 1182 10.1038/ncomms2155
32. Moreels, I.; Martins, J. C.; Hens, Z. Solution NMR Techniques for Investigating Colloidal Nanocrystal Ligands: A Case Study on Trioctylphosphine Oxide at InP Quantum Dots Sens. Actuators, B 2007, 126, 283-288 10.1016/j.snb.2006.12.026
33. Sachleben, J. R.; Colvin, V.; Emsley, L.; Wooten, E. W.; Alivisatos, A. P. Solution-State Nmr Studies of the Surface Structure and Dynamics of Semiconductor Nanocrystals J. Phys. Chem. B 1998, 102, 10117-10128 10.1021/jp9820121
34. Song, Y.; Harper, A. S.; Murray, R. W. Ligand Heterogeneity on Monolayer-Protected Gold Clusters Langmuir 2005, 21, 5492-5500 10.1021/la0503606
35. Terrill, R. H.; Postlethwaite, T. A.; Chen, C.-h.; Poon, C.-D.; Terzis, A.; Chen, A.; Hutchison, J. E.; Clark, M. R.; Wignall, G. Monolayers in Three Dimensions: Nmr, Saxs, Thermal, and Electron Hopping Studies of Alkanethiol Stabilized Gold Clusters J. Am. Chem. Soc. 1995, 117, 12537-12548 10.1021/ja00155a017
36. Zhang, B.; Yan, B. Analytical Strategies for Characterizing the Surface Chemistry of Nanoparticles Anal. Bioanal. Chem. 2010, 396, 973-982 10.1007/s00216-009-2996-1
37. Marbella, L. E.; Millstone, J. E. Nmr Techniques for Noble Metal Nanoparticles Chem. Mater. 2015, 27, 2721-2739 10.1021/cm504809c
38. Schapotschnikow, P.; Hommersom, B.; Vlugt, T. J. H. Adsorption and Binding of Ligands to CdSe Nanocrystals J. Phys. Chem. C 2009, 113, 12690-12698 10.1021/jp903291d
39. Munro, A. M.; Jen-La Plante, I.; Ng, M. S.; Ginger, D. S. Quantitative Study of the Effects of Surface Ligand Con-Centration on CdSe Nanocrystal Photoluminescence J. Phys. Chem. C 2007, 111, 6220-6227 10.1021/jp068733e
40. Gomes, R.; Hassinen, A.; Szczygiel, A.; Zhao, Q.; Vantomme, A.; Martins, J. C.; Hens, Z. Binding of Phosphonic Acids to CdSe Quantum Dots: A Solution Nmr Study J. Phys. Chem. Lett. 2011, 2, 145-152 10.1021/jz1016729
41. Kim, H. J.; Yoon, J. H.; Yoon, S. Photooxidative Coupling of Thiophenol Derivatives to Disulfides J. Phys. Chem. A 2010, 114, 12010-12015 10.1021/jp1077483
42. Teunis, M. B.; Dolai, S.; Sardar, R. Effects of Surface-Passivating Ligands and Ultrasmall CdSe Nanocrystal Size on the Delocalization of Exciton Confinement Langmuir 2014, 30, 7851-7858 10.1021/la501533t
43. Knowles, K. E.; Tice, D. B.; McArthur, E. A.; Solomon, G. C.; Weiss, E. A. Chemical Control of the Photoluminescence of CdSe Quantum Dot-Organic Complexes with a Series of Para-Substituted Aniline Ligands J. Am. Chem. Soc. 2010, 132, 1041-1050 10.1021/ja907253s
44. 13C NMR Spectroscopy and Ab Initio Calculations: Relations to the Hammett Parameters and Atomic Charges New J. Chem. 2003, 27, 1115-1123 10.1039/b300048f
45. Bordwell, F. G.; Zhang, X.-M.; Satish, A. V.; Cheng, J. P. Assessment of the Importance of Changes in Ground-State Energies on the Bond Dissociation Enthalpies of the O-H Bonds in Phenols and the S-H Bonds in Thiophenols J. Am. Chem. Soc. 1994, 116, 6605-6610 10.1021/ja00094a015
46. Jasieniak, J.; Califano, M.; Watkins, S. E. Size-Dependent Valence and Conduction Band-Edge Energies of Semiconductor Nanocrystals ACS Nano 2011, 5, 5888-5902 10.1021/nn201681s
47. Bryant, M. A.; Joa, S. L.; Pemberton, J. E. Raman Scattering from Monolayer Films of Thiophenol and 4-Mercaptopyridine at Pt Surfaces Langmuir 1992, 8, 753-756 10.1021/la00039a002
48. 2 Inorg. Chem. 1988, 27, 2781-2785 10.1021/ic00289a008
49. Anderson, N. C.; Hendricks, M. P.; Choi, J. J.; Owen, J. S. Ligand Exchange and the Stoichiometry of Metal Chalcogenide Nanocrystals: Spectroscopic Observation of Facile Metal-Carboxylate Displacement and Binding J. Am. Chem. Soc. 2013, 135, 18536-18548 10.1021/ja4086758
50. Fritzinger, B.; Capek, R. K.; Lambert, K.; Martins, J. C.; Hens, Z. Utilizing Self-Exchange to Address the Binding of Carboxylic Acid Ligands to CdSe Quantum Dots J. Am. Chem. Soc. 2010, 132, 10195-10201 10.1021/ja104351q
51. Taylor, J.; Kippeny, T.; Rosenthal, S. J. Surface Stoichiometry of CdSe Nanocrystals Determined by Rutherford Back-Scattering Spectroscopy J. Cluster Sci. 2001, 12, 571-582 10.1023/A:1014246315331