Elucidating the Solution-Phase Structure and Behavior of 8-Hydroxyquinoline Zinc in DMSO
Abstract
Here, the solution-phase structure and electronic relaxation dynamics of zinc bis-8-hydroxyquinoline [Zn(8HQ)2] in dimethyl sulfoxide (DMSO) were examined using a broad array of spectroscopic techniques, complimented by ab initio calculations of molecular structure. The ground-state structure was determined using extended X-ray absorption fine structure (EXAFS) data collected on the Zn Kedge and diffusion ordered spectroscopy (DOSY) NMR The complex was found to be monomeric and octahedral, with two bidentate 8-hydroxyquinolate ligands and two DMSO molecules coordinated to the zinc through oxygen atoms. Electronic relaxation dynamics were examined with ultrafast transient absorption spectroscopy and complementary density functional calculations. Electronic relaxation was observed to proceed through both singlet and triplet pathways. This solution-phase data provides a deeper physical understanding of the behavior of this molecule, which has a variety of uses such as sensing, OLEDs, and biological applications.
- Authors:
-
- DePaul Univ., Chicago, IL (United States). Dept. of Chemistry and Biochemistry
- Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
- State Univ. of New York (SUNY) The College of Brockport, Brockport, NY (United States). Dept. of Chemistry and Biochemistry
- Publication Date:
- Research Org.:
- Argonne National Lab. (ANL), Argonne, IL (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF); Univ. of Chicago, Chicago, IL (United States). Materials Research Science & Engineering Center (MRSEC)
- OSTI Identifier:
- 1461295
- Grant/Contract Number:
- AC02-06CH11357; DMR-1420709
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory
- Additional Journal Information:
- Journal Volume: 122; Journal Issue: 11; Journal ID: ISSN 1089-5639
- Publisher:
- American Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Zinc 8-hydroxyquinoline; Transient Absorption Spectroscopy; EXAFS; Density Functional Theory; DOSY NMR
Citation Formats
Grice, Kyle A., Griffin, Graham B., Cao, Phoebus Sun, Saucedo, Cesar, Niyazi, Aeshah H., Aldakheel, Fatimah A., Sterbinsky, George E., and LeSuer, Robert J. Elucidating the Solution-Phase Structure and Behavior of 8-Hydroxyquinoline Zinc in DMSO. United States: N. p., 2018.
Web. doi:10.1021/acs.jpca.7b12632.
Grice, Kyle A., Griffin, Graham B., Cao, Phoebus Sun, Saucedo, Cesar, Niyazi, Aeshah H., Aldakheel, Fatimah A., Sterbinsky, George E., & LeSuer, Robert J. Elucidating the Solution-Phase Structure and Behavior of 8-Hydroxyquinoline Zinc in DMSO. United States. https://doi.org/10.1021/acs.jpca.7b12632
Grice, Kyle A., Griffin, Graham B., Cao, Phoebus Sun, Saucedo, Cesar, Niyazi, Aeshah H., Aldakheel, Fatimah A., Sterbinsky, George E., and LeSuer, Robert J. Tue .
"Elucidating the Solution-Phase Structure and Behavior of 8-Hydroxyquinoline Zinc in DMSO". United States. https://doi.org/10.1021/acs.jpca.7b12632. https://www.osti.gov/servlets/purl/1461295.
@article{osti_1461295,
title = {Elucidating the Solution-Phase Structure and Behavior of 8-Hydroxyquinoline Zinc in DMSO},
author = {Grice, Kyle A. and Griffin, Graham B. and Cao, Phoebus Sun and Saucedo, Cesar and Niyazi, Aeshah H. and Aldakheel, Fatimah A. and Sterbinsky, George E. and LeSuer, Robert J.},
abstractNote = {Here, the solution-phase structure and electronic relaxation dynamics of zinc bis-8-hydroxyquinoline [Zn(8HQ)2] in dimethyl sulfoxide (DMSO) were examined using a broad array of spectroscopic techniques, complimented by ab initio calculations of molecular structure. The ground-state structure was determined using extended X-ray absorption fine structure (EXAFS) data collected on the Zn Kedge and diffusion ordered spectroscopy (DOSY) NMR The complex was found to be monomeric and octahedral, with two bidentate 8-hydroxyquinolate ligands and two DMSO molecules coordinated to the zinc through oxygen atoms. Electronic relaxation dynamics were examined with ultrafast transient absorption spectroscopy and complementary density functional calculations. Electronic relaxation was observed to proceed through both singlet and triplet pathways. This solution-phase data provides a deeper physical understanding of the behavior of this molecule, which has a variety of uses such as sensing, OLEDs, and biological applications.},
doi = {10.1021/acs.jpca.7b12632},
journal = {Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory},
number = 11,
volume = 122,
place = {United States},
year = {Tue Mar 06 00:00:00 EST 2018},
month = {Tue Mar 06 00:00:00 EST 2018}
}
Web of Science
Figures / Tables:
Works referenced in this record:
Coordination complexes exhibiting room-temperature phosphorescence: Evaluation of their suitability as triplet emitters in organic light emitting diodes
journal, August 2006
- Evans, Rachel C.; Douglas, Peter; Winscom, Christopher J.
- Coordination Chemistry Reviews, Vol. 250, Issue 15-16
New Trends in the Use of Transition Metal-Ligand Complexes for Applications in Electroluminescent Devices
journal, May 2005
- Holder, E.; Langeveld, B. M. W.; Schubert, U. S.
- Advanced Materials, Vol. 17, Issue 9
Phosphorescent Dyes for Organic Light-Emitting Diodes
journal, January 2007
- Chou, Pi-Tai; Chi, Yun
- Chemistry - A European Journal, Vol. 13, Issue 2
Visible light photoredox catalysis: applications in organic synthesis
journal, January 2011
- Narayanam, Jagan M. R.; Stephenson, Corey R. J.
- Chem. Soc. Rev., Vol. 40, Issue 1
Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis
journal, March 2013
- Prier, Christopher K.; Rankic, Danica A.; MacMillan, David W. C.
- Chemical Reviews, Vol. 113, Issue 7
Solar Synthesis: Prospects in Visible Light Photocatalysis
journal, February 2014
- Schultz, D. M.; Yoon, T. P.
- Science, Vol. 343, Issue 6174
Dye-Sensitized Solar Cells
journal, November 2010
- Hagfeldt, Anders; Boschloo, Gerrit; Sun, Licheng
- Chemical Reviews, Vol. 110, Issue 11
Solar Energy Conversion by Dye-Sensitized Photovoltaic Cells
journal, October 2005
- Grätzel, Michael
- Inorganic Chemistry, Vol. 44, Issue 20
Photophysics, photochemistry and solar energy conversion with tris(bipyridyl)ruthenium(II) and its analogues
journal, October 1982
- Kalyanasundaram, K.
- Coordination Chemistry Reviews, Vol. 46
Synthetically Tailored Excited States: Phosphorescent, Cyclometalated Iridium(III) Complexes and Their Applications
journal, October 2006
- Lowry, Michael S.; Bernhard, Stefan
- Chemistry - A European Journal, Vol. 12, Issue 31
8-Hydroxyquinolines: a review of their metal chelating properties and medicinal applications
journal, October 2013
- Prachayasittikul, Virapong; Prachayasittikul, Veda; Prachayasittikul, Supaluk
- Drug Design, Development and Therapy
8-Hydroxyquinoline: a privileged structure with a broad-ranging pharmacological potential
journal, January 2015
- Song, Yu'ning; Xu, Hao; Chen, Wenmin
- MedChemComm, Vol. 6, Issue 1
Copper-Dependent Cytotoxicity of 8-Hydroxyquinoline Derivatives Correlates with Their Hydrophobicity and Does Not Require Caspase Activation
journal, November 2012
- Tardito, Saverio; Barilli, Amelia; Bassanetti, Irene
- Journal of Medicinal Chemistry, Vol. 55, Issue 23
Optical, Magnetic, Electrochemical, and Electrical Properties of 8-Hydroxyquinoline-Based Complexes with Al 3+ , Cr 3+ , Mn 2+ , Co 2+ , Ni 2+ , Cu 2+ , and Zn 2+
journal, April 2011
- Monzon, Lorena M. A.; Burke, Franklyn; Coey, J. M. D.
- The Journal of Physical Chemistry C, Vol. 115, Issue 18
8-Hydroxyquinolines in metallosupramolecular chemistry
journal, April 2008
- Albrecht, Markus; Fiege, Marcel; Osetska, Olga
- Coordination Chemistry Reviews, Vol. 252, Issue 8-9
Electroluminescent Zinc(II) Bis(8-hydroxyquinoline): Structural Effects on Electronic States and Device Performance
journal, May 2002
- Sapochak, Linda S.; Benincasa, Flocerfida E.; Schofield, Richard S.
- Journal of the American Chemical Society, Vol. 124, Issue 21
The Crystal and Molecular Structure of Anhydrous Zinc 8-Quinolinolate Complex, [Zn(C 9 H 6 NO) 2 ] 4
journal, June 1985
- Kai, Yasushi; Morita, Masahiro; Yasuoka, Noritake
- Bulletin of the Chemical Society of Japan, Vol. 58, Issue 6
Highly Luminescent Zinc(II)−Bis(8-hydroxyquinoline) Complex Nanorods: Sonochemical Synthesis, Characterizations, and Protein Sensing
journal, May 2007
- Pan, Hong-Cheng; Liang, Fu-Pei; Mao, Chang-Jie
- The Journal of Physical Chemistry B, Vol. 111, Issue 20
New approach to synthesize 8-hydroxyquinoline-based complexes with Zn2+ and their luminescent properties
journal, December 2013
- Wang, Ruifang; Cao, Yali; Jia, Dianzeng
- Optical Materials, Vol. 36, Issue 2
Understanding M–ligand bonding and mer-/fac-isomerism in tris(8-hydroxyquinolinate) metallic complexes
journal, January 2016
- Lima, Carlos F. R. A. C.; Taveira, Ricardo J. S.; Costa, José C. S.
- Physical Chemistry Chemical Physics, Vol. 18, Issue 24
Diaquabis(8-quinolinolato-κ 2 N , O )zinc(II)
journal, August 2003
- Chen, Zhen-Feng; Zhang, Ming; Shi, Shao-Ming
- Acta Crystallographica Section E Structure Reports Online, Vol. 59, Issue 9
The crystal structure of zinc 8-hydroxyquinolinate dihydrate
journal, July 1954
- Merritt, L. L.; Cady, R. T.; Mundy, B. W.
- Acta Crystallographica, Vol. 7, Issue 6
Supramolecular Structures of Zinc (II) (8-Quinolinolato) Chelates †
journal, June 2004
- Sapochak, Linda S.; Falkowitz, Anna; Ferris, Kim F.
- The Journal of Physical Chemistry B, Vol. 108, Issue 25
Ligation of Bipyridyl Ligands to Metal 8-Hydroxyquinolinates - Synthesis, Crystal Structures, and TDDFT Study
journal, November 2008
- Yue, Fan; Zhu, Ai-Xin; Zheng, Shao-Liang
- European Journal of Inorganic Chemistry, Vol. 2008, Issue 32
Structural comparison of suberanilohydroxamic acid (SAHA) and other zinc-enzyme inhibitors bound to a monomeric zinc species
journal, August 2016
- Sun Cao, Phoebus; Sommer, Roger D.; Grice, Kyle A.
- Polyhedron, Vol. 114
ATHENA , ARTEMIS , HEPHAESTUS : data analysis for X-ray absorption spectroscopy using IFEFFIT
journal, June 2005
- Ravel, B.; Newville, M.
- Journal of Synchrotron Radiation, Vol. 12, Issue 4
Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields
journal, November 1994
- Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.
- The Journal of Physical Chemistry, Vol. 98, Issue 45, p. 11623-11627
Density‐functional thermochemistry. III. The role of exact exchange
journal, April 1993
- Becke, Axel D.
- The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
journal, January 1988
- Lee, Chengteh; Yang, Weitao; Parr, Robert G.
- Physical Review B, Vol. 37, Issue 2
Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis
journal, August 1980
- Vosko, S. H.; Wilk, L.; Nusair, M.
- Canadian Journal of Physics, Vol. 58, Issue 8
Self‐consistent molecular orbital methods 25. Supplementary functions for Gaussian basis sets
journal, April 1984
- Frisch, Michael J.; Pople, John A.; Binkley, J. Stephen
- The Journal of Chemical Physics, Vol. 80, Issue 7
Quantum Mechanical Continuum Solvation Models
journal, August 2005
- Tomasi, Jacopo; Mennucci, Benedetta; Cammi, Roberto
- Chemical Reviews, Vol. 105, Issue 8
Soft X‐Ray Absorption Edges of Metal Ions in Complexes. III. Zinc (II) Complexes
journal, January 1958
- Cotton, F. Albert; Hanson, Harold P.
- The Journal of Chemical Physics, Vol. 28, Issue 1
The usefulness of 2D DOSY and 3D DOSY-COSY 1 H NMR for mixture analysis: application to genuine and fake formulations of sildenafil (Viagra): Detection of counterfeit Viagra with 2D DOSY and 3D DOSY-COSY 1 H NMR
journal, August 2009
- Trefi, Saleh; Gilard, Véronique; Balayssac, Stéphane
- Magnetic Resonance in Chemistry, Vol. 47, Issue S1
Polydispersity index of polymers revealed by DOSY NMR
journal, September 2011
- Viéville, Justine; Tanty, Matthieu; Delsuc, Marc-André
- Journal of Magnetic Resonance, Vol. 212, Issue 1
Diffusion-Ordered NMR Spectroscopy as a Reliable Alternative to TEM for Determining the Size of Gold Nanoparticles in Organic Solutions
journal, April 2011
- Canzi, Gabriele; Mrse, Anthony A.; Kubiak, Clifford P.
- The Journal of Physical Chemistry C, Vol. 115, Issue 16
Influence of the protonation, deprotonation and transition metal ions on the fluorescence of 8-hydroxyquinoline: a computational study
journal, September 2011
- Elroby, Shabaan A. K.; El-Shishtawy, Reda M.; Makki, M. S. I.
- Molecular Simulation, Vol. 37, Issue 11
Potential levels of metal complexes of 8-hydroxyquinoline
journal, October 2016
- Nishikiori, Hiromasa; Nakamura, Shogo; Natori, Daichi
- Chemical Physics Letters, Vol. 662
Synthesis, structure, and spectroscopic properties of copper( II ) compounds containing nitrogen–sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2′-yl)-2,6-dithiaheptane]copper( II ) perchlorate
journal, January 1984
- Addison, Anthony W.; Rao, T. Nageswara; Reedijk, Jan
- J. Chem. Soc., Dalton Trans., Issue 7
Synthesis and Structural Studies of Nickel(0) Tetracarbene Complexes with the Introduction of a New Four-Coordinate Geometric Index, τ δ
journal, March 2015
- Reineke, Mark H.; Sampson, Matthew D.; Rheingold, Arnold L.
- Inorganic Chemistry, Vol. 54, Issue 7
The effects of crystal structure on optical absorption/photoluminescence of bis(8-hydroxyquinoline)zinc
journal, November 2005
- Bing-she, Xu; Yu-ying, Hao; Hua, Wang
- Solid State Communications, Vol. 136, Issue 6
Substituted Aluminum and Zinc Quinolates with Blue-Shifted Absorbance/Luminescence Bands: Synthesis and Spectroscopic, Photoluminescence, and Electroluminescence Characterization
journal, January 1996
- Hopkins, T. A.; Meerholz, K.; Shaheen, S.
- Chemistry of Materials, Vol. 8, Issue 2
Photolysis of Zn(8-quinolinolate)2(H2O)2 in non-aqueous solution. Photoactivation of hydrolysis
journal, July 2014
- Vogler, Arnd
- Inorganic Chemistry Communications, Vol. 45
A Picosecond Hard X-ray Study of the Fluorescence Dynamics of Anthracene Derivatives and 8-Hydroxyquinoline Complex Microcrystals
journal, May 2009
- Odaka, Hideho; Miura, Toshifumi; Hatanaka, Koji
- The Journal of Physical Chemistry C, Vol. 113, Issue 27
Metal Quinolinolate−Fullerene(s) Donor−Acceptor Complexes: Evidence for Organic LED Molecules Acting as Electron Donors in Photoinduced Electron-Transfer Reactions
journal, November 2008
- D’Souza, Francis; Maligaspe, Eranda; Zandler, Melvin E.
- Journal of the American Chemical Society, Vol. 130, Issue 50
Characterization of the Triplet State of Tris(8-hydroxyquinoline)aluminium(III) in Benzene Solution
journal, December 2003
- Burrows, Hugh D.; Fernandes, Mariana; Seixas de Melo, J.
- Journal of the American Chemical Society, Vol. 125, Issue 50
Triplet photosensitizers: from molecular design to applications
journal, January 2013
- Zhao, Jianzhang; Wu, Wanhua; Sun, Jifu
- Chemical Society Reviews, Vol. 42, Issue 12
Stabilizing triplet excited states for ultralong organic phosphorescence
journal, April 2015
- An, Zhongfu; Zheng, Chao; Tao, Ye
- Nature Materials, Vol. 14, Issue 7
Works referencing / citing this record:
The nature of binding of quinolate complex on the surface of ZnS quantum dots
journal, January 2019
- Roy, Shilaj; Bhandari, Satyapriya; Manna, Mihir
- Physical Chemistry Chemical Physics, Vol. 21, Issue 2