Anthracene Diphosphate Ligands for CdSe Quantum Dots; Molecular Design for Efficient Upconversion

De Roo, Jonathan; Huang, Zhiyuan; Schuster, Nathaniel J.; Hamachi, Leslie S.; Congreve, Daniel N.; Xu, Zihao; Xia, Pan; Fishman, Dmitry A.; Lian, Tianquan; Owen, Jonathan S.; Tang, Ming Lee

doi:10.1021/acs.chemmater.9b04294

Title: Anthracene Diphosphate Ligands for CdSe Quantum Dots; Molecular Design for Efficient Upconversion

Journal Article · 22 January 2020 · Chemistry of Materials

DOI: https://doi.org/10.1021/acs.chemmater.9b04294 · OSTI ID:1773896

^[1];

^[2]; Schuster, Nathaniel J. ^[3]; Hamachi, Leslie S. ^[3];

^[4];

^[5];

^[2]; Fishman, Dmitry A. ^[2];

^[5];

^[3];

^[2]

Columbia Univ., New York, NY (United States); Univ. of Basel (Switzerland); UC Riverside
Univ. of California, Riverside, CA (United States)
Columbia Univ., New York, NY (United States)
Harvard Univ., Cambridge, MA (United States)
Emory Univ., Atlanta, GA (United States)

Quantum dot (QD)-sensitized photon upconversion follows a multi-step energy transfer process from the QD to transmitter ligand to a soluble annihilator. Using a novel 10-R-anthracene-1,8-diphosphoric acid (R = octyl, 2- hexyldecyl, phenyl) ligand with high binding affinity for CdSe QD surfaces, we demonstrate a photon upconversion process that is limited by the transmitter to annihilator transfer efficiency. Using ¹H NMR spectroscopy, we demonstrate that these bidentate diphosphate ligands rapidly and irreversibly displace two carboxylate ligands. These ligands mediate energy transfer from the photoexcited QDs to a triplet annihilator (1,10-diphenylanthracene), producing overall photon upconversion quantum efficiencies as high as 17%, the highest for QDs with no shells. In conclusion, transient absorption spectroscopy shows that the anthracene dihydrogen phosphate (ADP) ligand supports a 3.4 fold longer triplet state lifetime compared to 9-anthracene carboxylic acid (299.9 ± 9.5 vs 88.2 ± 2.1 μs), increasing the probability of energy transfer.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Univ. of California, Riverside, CA (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: SC0008798; SC0018969

OSTI ID:: 1773896

Journal Information:: Chemistry of Materials, Journal Name: Chemistry of Materials Journal Issue: 4 Vol. 32; ISSN 0897-4756

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (35)

Electrochemical Multiplexing: Control over Surface Functionalization by Combining a Redox-Sensitive Alkyne Protection Group with “Click”-Chemistry Hellstern, Manuel; Gantenbein, Markus; Le Pleux, Loïc Advanced Materials Interfaces, Vol. 6, Issue 5 https://doi.org/10.1002/admi.201801917	journal	January 2019
Synthesis of Metal-Selenide Nanocrystals Using Selenium Dioxide as the Selenium Precursor Chen, Ou; Chen, Xian; Yang, Yongan Angewandte Chemie International Edition, Vol. 47, Issue 45 https://doi.org/10.1002/anie.200804266	journal	October 2008
Complementary Lock-and-Key Ligand Binding of a Triplet Transmitter to a Nanocrystal Photosensitizer Li, Xin; Fast, Alexander; Huang, Zhiyuan Angewandte Chemie International Edition, Vol. 56, Issue 20 https://doi.org/10.1002/anie.201701929	journal	April 2017
PbS/CdS Core-Shell Quantum Dots Suppress Charge Transfer and Enhance Triplet Transfer Huang, Zhiyuan; Xu, Zihao; Mahboub, Melika Angewandte Chemie International Edition, Vol. 56, Issue 52 https://doi.org/10.1002/anie.201710224	journal	November 2017
Triplet Sensitization by Lead Halide Perovskite Thin Films for Efficient Solid-State Photon Upconversion at Subsolar Fluxes Wieghold, Sarah; Bieber, Alexander S.; VanOrman, Zachary A. Matter, Vol. 1, Issue 3 https://doi.org/10.1016/j.matt.2019.05.026	journal	September 2019
Nanocrystal Size and Quantum Yield in the Upconversion of Green to Violet Light with CdSe and Anthracene Derivatives Huang, Zhiyuan; Li, Xin; Yip, Benjamin D. Chemistry of Materials, Vol. 27, Issue 21 https://doi.org/10.1021/acs.chemmater.5b03731	journal	October 2015
Quantifying Ligand Exchange Reactions at CdSe Nanocrystal Surfaces Knauf, Robin R.; Lennox, J. Christian; Dempsey, Jillian L. Chemistry of Materials, Vol. 28, Issue 13 https://doi.org/10.1021/acs.chemmater.6b01827	journal	June 2016
Probing Solvent–Ligand Interactions in Colloidal Nanocrystals by the NMR Line Broadening De Roo, Jonathan; Yazdani, Nuri; Drijvers, Emile Chemistry of Materials, Vol. 30, Issue 15 https://doi.org/10.1021/acs.chemmater.8b02523	journal	July 2018
A Versatile Coordinating Ligand for Coating Semiconductor, Metal, and Metal Oxide Nanocrystals Du, Liang; Wang, Wentao; Zhang, Chengqi Chemistry of Materials, Vol. 30, Issue 20 https://doi.org/10.1021/acs.chemmater.8b03527	journal	September 2018
Synthesis of Phosphonic Acid Ligands for Nanocrystal Surface Functionalization and Solution Processed Memristors De Roo, Jonathan; Zhou, Zimu; Wang, Jiaying Chemistry of Materials, Vol. 30, Issue 21 https://doi.org/10.1021/acs.chemmater.8b03768	journal	October 2018
Nanomaterials for In Vivo Imaging Smith, Bryan Ronain; Gambhir, Sanjiv Sam Chemical Reviews, Vol. 117, Issue 3 https://doi.org/10.1021/acs.chemrev.6b00073	journal	January 2017
Delayed Molecular Triplet Generation from Energized Lead Sulfide Quantum Dots Garakyaraghi, Sofia; Mongin, Cédric; Granger, Devin B. The Journal of Physical Chemistry Letters, Vol. 8, Issue 7 https://doi.org/10.1021/acs.jpclett.7b00546	journal	March 2017
Surface Traps in Colloidal Quantum Dots: A Combined Experimental and Theoretical Perspective Giansante, Carlo; Infante, Ivan The Journal of Physical Chemistry Letters, Vol. 8, Issue 20 https://doi.org/10.1021/acs.jpclett.7b02193	journal	October 2017
Visible-to-Ultraviolet Upconversion Efficiency above 10% Sensitized by Quantum-Confined Perovskite Nanocrystals He, Shan; Luo, Xiao; Liu, Xue The Journal of Physical Chemistry Letters, Vol. 10, Issue 17 https://doi.org/10.1021/acs.jpclett.9b02106	journal	August 2019
Amino Acid-Based Stabilization of Oxide Nanocrystals in Polar Media: From Insight in Ligand Exchange to Solution ¹ H NMR Probing of Short-Chained Adsorbates De Roo, Jonathan; Coucke, Sofie; Rijckaert, Hannes Langmuir, Vol. 32, Issue 8 https://doi.org/10.1021/acs.langmuir.5b04611	journal	February 2016
Hybrid Molecule–Nanocrystal Photon Upconversion Across the Visible and Near-Infrared Huang, Zhiyuan; Li, Xin; Mahboub, Melika Nano Letters, Vol. 15, Issue 8 https://doi.org/10.1021/acs.nanolett.5b02130	journal	July 2015
Control of Energy Flow Dynamics between Tetracene Ligands and PbS Quantum Dots by Size Tuning and Ligand Coverage Kroupa, Daniel M.; Arias, Dylan H.; Blackburn, Jeffrey L. Nano Letters, Vol. 18, Issue 2 https://doi.org/10.1021/acs.nanolett.7b04144	journal	January 2018
Experimental Determination of the Extinction Coefficient of CdTe, CdSe, and CdS Nanocrystals Yu, W. William; Qu, Lianhua; Guo, Wenzhuo Chemistry of Materials, Vol. 15, Issue 14, p. 2854-2860 https://doi.org/10.1021/cm034081k	journal	July 2003
A Solution NMR Toolbox for Characterizing the Surface Chemistry of Colloidal Nanocrystals Hens, Zeger; Martins, José C. Chemistry of Materials, Vol. 25, Issue 8 https://doi.org/10.1021/cm303361s	journal	February 2013
Reaction Chemistry and Ligand Exchange at Cadmium−Selenide Nanocrystal Surfaces Owen, Jonathan S.; Park, Jungwon; Trudeau, Paul-Emile Journal of the American Chemical Society, Vol. 130, Issue 37 https://doi.org/10.1021/ja804414f	journal	September 2008
Designing Transmitter Ligands That Mediate Energy Transfer between Semiconductor Nanocrystals and Molecules Huang, Zhiyuan; Tang, Ming L. Journal of the American Chemical Society, Vol. 139, Issue 28 https://doi.org/10.1021/jacs.6b08783	journal	June 2017
Finding and Fixing Traps in II–VI and III–V Colloidal Quantum Dots: The Importance of Z-Type Ligand Passivation Kirkwood, Nicholas; Monchen, Julius O. V.; Crisp, Ryan W. Journal of the American Chemical Society, Vol. 140, Issue 46 https://doi.org/10.1021/jacs.8b07783	journal	October 2018
Enhanced Near-Infrared-to-Visible Upconversion by Synthetic Control of PbS Nanocrystal Triplet Photosensitizers Huang, Zhiyuan; Xu, Zihao; Mahboub, Melika Journal of the American Chemical Society, Vol. 141, Issue 25 https://doi.org/10.1021/jacs.9b03385	journal	June 2019
Triplet Sensitization by “Self-Trapped” Excitons of Nontoxic CuInS ₂ Nanocrystals for Efficient Photon Upconversion Han, Yaoyao; He, Shan; Luo, Xiao Journal of the American Chemical Society, Vol. 141, Issue 33 https://doi.org/10.1021/jacs.9b07033	journal	August 2019
A Citric Acid-Derived Ligand for Modular Functionalization of Metal Oxide Surfaces via “Click” Chemistry Bishop, Lee M.; Yeager, Joseph C.; Chen, Xin Langmuir, Vol. 28, Issue 2 https://doi.org/10.1021/la204145t	journal	December 2011
Synthesis and Micrometer-Scale Assembly of Colloidal CdSe/CdS Nanorods Prepared by a Seeded Growth Approach Carbone, Luigi; Nobile, Concetta; De Giorgi, Milena Nano Letters, Vol. 7, Issue 10 https://doi.org/10.1021/nl0717661	journal	October 2007
Thermally activated delayed photoluminescence from pyrenyl-functionalized CdSe quantum dots Mongin, Cédric; Moroz, Pavel; Zamkov, Mikhail Nature Chemistry, Vol. 10, Issue 2 https://doi.org/10.1038/nchem.2906	journal	December 2017
Photoredox catalysis using infrared light via triplet fusion upconversion Ravetz, Benjamin D.; Pun, Andrew B.; Churchill, Emily M. Nature, Vol. 565, Issue 7739 https://doi.org/10.1038/s41586-018-0835-2	journal	January 2019
Liquid crystals containing a 2,6-disubstituted anthracene core—mesomorphism, charge transport and photochemical properties Méry, Stéphane; Haristoy, Denis; Nicoud, Jean-François J. Mater. Chem., Vol. 13, Issue 7 https://doi.org/10.1039/b211867j	journal	January 2003
Low power, non-coherent sensitized photon up-conversion: modelling and perspectives Monguzzi, Angelo; Tubino, Riccardo; Hoseinkhani, Sajjad Physical Chemistry Chemical Physics, Vol. 14, Issue 13 https://doi.org/10.1039/c2cp23900k	journal	January 2012
Ligand enhanced upconversion of near-infrared photons with nanocrystal light absorbers Huang, Zhiyuan; Simpson, Duane E.; Mahboub, Melika Chemical Science, Vol. 7, Issue 7 https://doi.org/10.1039/c6sc00257a	journal	January 2016
Triplet sensitization by perovskite nanocrystals for photon upconversion Mase, Kazuma; Okumura, Keisuke; Yanai, Nobuhiro Chemical Communications, Vol. 53, Issue 59 https://doi.org/10.1039/c7cc03087h	journal	January 2017
Effect of substituent on the behaviour of the excited singlet and triplet states in carbonyl derivatives of anthracene of the type 9-X·CO·A Hirayama, Satoshi Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, Vol. 78, Issue 8 https://doi.org/10.1039/f19827802411	journal	January 1982
SYNTHESIS OF HYDROLYTICALLY STABLE tert -BUTYLDIMETHYLSILYL ETHERS OF HYDROXYANTHRAQUINONES Bakola-christianopoulou, Maria N.; Apazidou, Katerina K. Phosphorus, Sulfur, and Silicon and the Related Elements, Vol. 113, Issue 1-4 https://doi.org/10.1080/10426509608046395	journal	June 1996
Direct observation of triplet energy transfer from semiconductor nanocrystals Mongin, C.; Garakyaraghi, S.; Razgoniaeva, N. Science, Vol. 351, Issue 6271 https://doi.org/10.1126/science.aad6378	journal	January 2016

Similar Records

Photon Upconversion at Organic-Inorganic Interfaces

Journal Article · 2024 · Annual Review of Physical Chemistry · OSTI ID:2568388

Huang, Zhiyuan; Miyashita, Tsumugi; Tang, Ming Lee

Quantifying the Ligand-Induced Triplet Energy Transfer Barrier in a Quantum Dot-Based Upconversion System

Journal Article · 2022 · Journal of Physical Chemistry Letters · OSTI ID:2568385

Miyashita, Tsumugi; Jaimes, Paulina; Lian, Tianquan; +2 more

Direct triplet sensitization of oligothiophene by quantum dots

Journal Article · 2019 · Chemical Science · OSTI ID:1514725

Xu, Zihao; Jin, Tao; Huang, Yiming; +4 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Cadmium selenide
Energy transfer
Ligands
Luminescence
Quantum dots

Title: Anthracene Diphosphate Ligands for CdSe Quantum Dots; Molecular Design for Efficient Upconversion

Citation Formats

References (35)

Similar Records

Related Subjects