Elucidating the Solution-Phase Structure and Behavior of 8-Hydroxyquinoline Zinc in DMSO

Grice, Kyle A.; Griffin, Graham B.; Cao, Phoebus Sun; Saucedo, Cesar; Niyazi, Aeshah H.; Aldakheel, Fatimah A.; Sterbinsky, George E.; LeSuer, Robert J.

doi:10.1021/acs.jpca.7b12632

Title: Elucidating the Solution-Phase Structure and Behavior of 8-Hydroxyquinoline Zinc in DMSO

Journal Article · Tue Mar 06 00:00:00 EST 2018 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI:https://doi.org/10.1021/acs.jpca.7b12632· OSTI ID:1461295

^[1];

^[1]; Cao, Phoebus Sun ^[1]; Saucedo, Cesar ^[1]; Niyazi, Aeshah H. ^[1]; Aldakheel, Fatimah A. ^[1]; Sterbinsky, George E. ^[2]; LeSuer, Robert J. ^[3]

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

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.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States)

Sponsoring Organization:: 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)

Grant/Contract Number:: AC02-06CH11357; DMR-1420709

OSTI ID:: 1461295

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Vol. 122, Issue 11; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 3 works

Citation information provided by
Web of Science

References (49)

Coordination complexes exhibiting room-temperature phosphorescence: Evaluation of their suitability as triplet emitters in organic light emitting diodes Evans, Rachel C.; Douglas, Peter; Winscom, Christopher J. Coordination Chemistry Reviews, Vol. 250, Issue 15-16 https://doi.org/10.1016/j.ccr.2006.02.007	journal	August 2006
New Trends in the Use of Transition Metal-Ligand Complexes for Applications in Electroluminescent Devices Holder, E.; Langeveld, B. M. W.; Schubert, U. S. Advanced Materials, Vol. 17, Issue 9 https://doi.org/10.1002/adma.200400284	journal	May 2005
Phosphorescent Dyes for Organic Light-Emitting Diodes Chou, Pi-Tai; Chi, Yun Chemistry - A European Journal, Vol. 13, Issue 2 https://doi.org/10.1002/chem.200601272	journal	January 2007
Visible light photoredox catalysis: applications in organic synthesis Narayanam, Jagan M. R.; Stephenson, Corey R. J. Chem. Soc. Rev., Vol. 40, Issue 1 https://doi.org/10.1039/B913880N	journal	January 2011
Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis Prier, Christopher K.; Rankic, Danica A.; MacMillan, David W. C. Chemical Reviews, Vol. 113, Issue 7 https://doi.org/10.1021/cr300503r	journal	March 2013
Solar Synthesis: Prospects in Visible Light Photocatalysis Schultz, D. M.; Yoon, T. P. Science, Vol. 343, Issue 6174 https://doi.org/10.1126/science.1239176	journal	February 2014
Photoelectrochemical cells Grätzel, Michael Nature, Vol. 414, Issue 6861 https://doi.org/10.1038/35104607	journal	November 2001
Dye-Sensitized Solar Cells Hagfeldt, Anders; Boschloo, Gerrit; Sun, Licheng Chemical Reviews, Vol. 110, Issue 11 https://doi.org/10.1021/cr900356p	journal	November 2010
Solar Energy Conversion by Dye-Sensitized Photovoltaic Cells Grätzel, Michael Inorganic Chemistry, Vol. 44, Issue 20 https://doi.org/10.1021/ic0508371	journal	October 2005
Photophysics, photochemistry and solar energy conversion with tris(bipyridyl)ruthenium(II) and its analogues Kalyanasundaram, K. Coordination Chemistry Reviews, Vol. 46 https://doi.org/10.1016/0010-8545(82)85003-0	journal	October 1982
Synthetically Tailored Excited States: Phosphorescent, Cyclometalated Iridium(III) Complexes and Their Applications Lowry, Michael S.; Bernhard, Stefan Chemistry - A European Journal, Vol. 12, Issue 31 https://doi.org/10.1002/chem.200600618	journal	October 2006
8-Hydroxyquinolines: a review of their metal chelating properties and medicinal applications Prachayasittikul, Virapong; Prachayasittikul, Veda; Prachayasittikul, Supaluk Drug Design, Development and Therapy https://doi.org/10.2147/DDDT.S49763	journal	October 2013
8-Hydroxyquinoline: a privileged structure with a broad-ranging pharmacological potential Song, Yu'ning; Xu, Hao; Chen, Wenmin MedChemComm, Vol. 6, Issue 1 https://doi.org/10.1039/C4MD00284A	journal	January 2015
Copper-Dependent Cytotoxicity of 8-Hydroxyquinoline Derivatives Correlates with Their Hydrophobicity and Does Not Require Caspase Activation Tardito, Saverio; Barilli, Amelia; Bassanetti, Irene Journal of Medicinal Chemistry, Vol. 55, Issue 23 https://doi.org/10.1021/jm301053a	journal	November 2012
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⁺ Monzon, Lorena M. A.; Burke, Franklyn; Coey, J. M. D. The Journal of Physical Chemistry C, Vol. 115, Issue 18 https://doi.org/10.1021/jp201019c	journal	April 2011
8-Hydroxyquinolines in metallosupramolecular chemistry Albrecht, Markus; Fiege, Marcel; Osetska, Olga Coordination Chemistry Reviews, Vol. 252, Issue 8-9 https://doi.org/10.1016/j.ccr.2007.06.003	journal	April 2008
Electroluminescent Zinc(II) Bis(8-hydroxyquinoline): Structural Effects on Electronic States and Device Performance Sapochak, Linda S.; Benincasa, Flocerfida E.; Schofield, Richard S. Journal of the American Chemical Society, Vol. 124, Issue 21 https://doi.org/10.1021/ja0201909	journal	May 2002
The Crystal and Molecular Structure of Anhydrous Zinc 8-Quinolinolate Complex, [Zn(C ₉ H ₆ NO) ₂ ] ₄ Kai, Yasushi; Morita, Masahiro; Yasuoka, Noritake Bulletin of the Chemical Society of Japan, Vol. 58, Issue 6 https://doi.org/10.1246/bcsj.58.1631	journal	June 1985
Highly Luminescent Zinc(II)−Bis(8-hydroxyquinoline) Complex Nanorods: Sonochemical Synthesis, Characterizations, and Protein Sensing Pan, Hong-Cheng; Liang, Fu-Pei; Mao, Chang-Jie The Journal of Physical Chemistry B, Vol. 111, Issue 20 https://doi.org/10.1021/jp0703049	journal	May 2007
New approach to synthesize 8-hydroxyquinoline-based complexes with Zn2+ and their luminescent properties Wang, Ruifang; Cao, Yali; Jia, Dianzeng Optical Materials, Vol. 36, Issue 2 https://doi.org/10.1016/j.optmat.2013.08.032	journal	December 2013
Understanding M–ligand bonding and mer-/fac-isomerism in tris(8-hydroxyquinolinate) metallic complexes Lima, Carlos F. R. A. C.; Taveira, Ricardo J. S.; Costa, José C. S. Physical Chemistry Chemical Physics, Vol. 18, Issue 24 https://doi.org/10.1039/C6CP02608G	journal	January 2016
Diaquabis(8-quinolinolato-κ ² N , O )zinc(II) Chen, Zhen-Feng; Zhang, Ming; Shi, Shao-Ming Acta Crystallographica Section E Structure Reports Online, Vol. 59, Issue 9 https://doi.org/10.1107/S1600536803018427	journal	August 2003
The crystal structure of zinc 8-hydroxyquinolinate dihydrate Merritt, L. L.; Cady, R. T.; Mundy, B. W. Acta Crystallographica, Vol. 7, Issue 6 https://doi.org/10.1107/S0365110X54001491	journal	July 1954
Supramolecular Structures of Zinc (II) (8-Quinolinolato) Chelates ^† Sapochak, Linda S.; Falkowitz, Anna; Ferris, Kim F. The Journal of Physical Chemistry B, Vol. 108, Issue 25 https://doi.org/10.1021/jp037074s	journal	June 2004
Ligation of Bipyridyl Ligands to Metal 8-Hydroxyquinolinates - Synthesis, Crystal Structures, and TDDFT Study Yue, Fan; Zhu, Ai-Xin; Zheng, Shao-Liang European Journal of Inorganic Chemistry, Vol. 2008, Issue 32 https://doi.org/10.1002/ejic.200800507	journal	November 2008
Structural comparison of suberanilohydroxamic acid (SAHA) and other zinc-enzyme inhibitors bound to a monomeric zinc species Sun Cao, Phoebus; Sommer, Roger D.; Grice, Kyle A. Polyhedron, Vol. 114 https://doi.org/10.1016/j.poly.2016.01.029	journal	August 2016
ATHENA , ARTEMIS , HEPHAESTUS : data analysis for X-ray absorption spectroscopy using IFEFFIT Ravel, B.; Newville, M. Journal of Synchrotron Radiation, Vol. 12, Issue 4 https://doi.org/10.1107/S0909049505012719	journal	June 2005
Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F. The Journal of Physical Chemistry, Vol. 98, Issue 45, p. 11623-11627 https://doi.org/10.1021/j100096a001	journal	November 1994
Density‐functional thermochemistry. III. The role of exact exchange Becke, Axel D. The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652 https://doi.org/10.1063/1.464913	journal	April 1993
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Lee, Chengteh; Yang, Weitao; Parr, Robert G. Physical Review B, Vol. 37, Issue 2 https://doi.org/10.1103/PhysRevB.37.785	journal	January 1988
Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis Vosko, S. H.; Wilk, L.; Nusair, M. Canadian Journal of Physics, Vol. 58, Issue 8 https://doi.org/10.1139/p80-159	journal	August 1980
Self‐consistent molecular orbital methods 25. Supplementary functions for Gaussian basis sets Frisch, Michael J.; Pople, John A.; Binkley, J. Stephen The Journal of Chemical Physics, Vol. 80, Issue 7 https://doi.org/10.1063/1.447079	journal	April 1984
Quantum Mechanical Continuum Solvation Models Tomasi, Jacopo; Mennucci, Benedetta; Cammi, Roberto Chemical Reviews, Vol. 105, Issue 8 https://doi.org/10.1021/cr9904009	journal	August 2005
Soft X‐Ray Absorption Edges of Metal Ions in Complexes. III. Zinc (II) Complexes Cotton, F. Albert; Hanson, Harold P. The Journal of Chemical Physics, Vol. 28, Issue 1 https://doi.org/10.1063/1.1744085	journal	January 1958
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 Trefi, Saleh; Gilard, Véronique; Balayssac, Stéphane Magnetic Resonance in Chemistry, Vol. 47, Issue S1 https://doi.org/10.1002/mrc.2490	journal	August 2009
Polydispersity index of polymers revealed by DOSY NMR Viéville, Justine; Tanty, Matthieu; Delsuc, Marc-André Journal of Magnetic Resonance, Vol. 212, Issue 1 https://doi.org/10.1016/j.jmr.2011.06.020	journal	September 2011
Diffusion-Ordered NMR Spectroscopy as a Reliable Alternative to TEM for Determining the Size of Gold Nanoparticles in Organic Solutions Canzi, Gabriele; Mrse, Anthony A.; Kubiak, Clifford P. The Journal of Physical Chemistry C, Vol. 115, Issue 16 https://doi.org/10.1021/jp2008557	journal	April 2011
Influence of the protonation, deprotonation and transition metal ions on the fluorescence of 8-hydroxyquinoline: a computational study Elroby, Shabaan A. K.; El-Shishtawy, Reda M.; Makki, M. S. I. Molecular Simulation, Vol. 37, Issue 11 https://doi.org/10.1080/08927022.2011.578137	journal	September 2011
Potential levels of metal complexes of 8-hydroxyquinoline Nishikiori, Hiromasa; Nakamura, Shogo; Natori, Daichi Chemical Physics Letters, Vol. 662 https://doi.org/10.1016/j.cplett.2016.07.023	journal	October 2016
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 Addison, Anthony W.; Rao, T. Nageswara; Reedijk, Jan J. Chem. Soc., Dalton Trans., Issue 7 https://doi.org/10.1039/DT9840001349	journal	January 1984
Synthesis and Structural Studies of Nickel(0) Tetracarbene Complexes with the Introduction of a New Four-Coordinate Geometric Index, τ _δ Reineke, Mark H.; Sampson, Matthew D.; Rheingold, Arnold L. Inorganic Chemistry, Vol. 54, Issue 7 https://doi.org/10.1021/ic502792q	journal	March 2015
The effects of crystal structure on optical absorption/photoluminescence of bis(8-hydroxyquinoline)zinc Bing-she, Xu; Yu-ying, Hao; Hua, Wang Solid State Communications, Vol. 136, Issue 6 https://doi.org/10.1016/j.ssc.2005.08.021	journal	November 2005
Substituted Aluminum and Zinc Quinolates with Blue-Shifted Absorbance/Luminescence Bands: Synthesis and Spectroscopic, Photoluminescence, and Electroluminescence Characterization Hopkins, T. A.; Meerholz, K.; Shaheen, S. Chemistry of Materials, Vol. 8, Issue 2 https://doi.org/10.1021/cm9503442	journal	January 1996
Photolysis of Zn(8-quinolinolate)2(H2O)2 in non-aqueous solution. Photoactivation of hydrolysis Vogler, Arnd Inorganic Chemistry Communications, Vol. 45 https://doi.org/10.1016/j.inoche.2014.04.013	journal	July 2014
A Picosecond Hard X-ray Study of the Fluorescence Dynamics of Anthracene Derivatives and 8-Hydroxyquinoline Complex Microcrystals Odaka, Hideho; Miura, Toshifumi; Hatanaka, Koji The Journal of Physical Chemistry C, Vol. 113, Issue 27 https://doi.org/10.1021/jp9031332	journal	May 2009
Metal Quinolinolate−Fullerene(s) Donor−Acceptor Complexes: Evidence for Organic LED Molecules Acting as Electron Donors in Photoinduced Electron-Transfer Reactions D’Souza, Francis; Maligaspe, Eranda; Zandler, Melvin E. Journal of the American Chemical Society, Vol. 130, Issue 50 https://doi.org/10.1021/ja805027r	journal	November 2008
Characterization of the Triplet State of Tris(8-hydroxyquinoline)aluminium(III) in Benzene Solution Burrows, Hugh D.; Fernandes, Mariana; Seixas de Melo, J. Journal of the American Chemical Society, Vol. 125, Issue 50 https://doi.org/10.1021/ja037254f	journal	December 2003
Triplet photosensitizers: from molecular design to applications Zhao, Jianzhang; Wu, Wanhua; Sun, Jifu Chemical Society Reviews, Vol. 42, Issue 12 https://doi.org/10.1039/c3cs35531d	journal	January 2013
Stabilizing triplet excited states for ultralong organic phosphorescence An, Zhongfu; Zheng, Chao; Tao, Ye Nature Materials, Vol. 14, Issue 7 https://doi.org/10.1038/nmat4259	journal	April 2015

Cited By (1)

The nature of binding of quinolate complex on the surface of ZnS quantum dots Roy, Shilaj; Bhandari, Satyapriya; Manna, Mihir Physical Chemistry Chemical Physics, Vol. 21, Issue 2 https://doi.org/10.1039/c8cp06235h	journal	January 2019

Figures / Tables (9)

Similar Records

Solution Chemistry of Copper(II) Binding to Substituted 8-Hydroxyquinolines

Journal Article · Wed Sep 16 00:00:00 EDT 2020 · Inorganic Chemistry · OSTI ID:1461295

Summers, Kelly L.; Pushie, M. Jake; Sopasis, George J.; +7 more

PBT2 acts through a different mechanism of action than other 8-hydroxyquinolines: an X-ray fluorescence imaging study

Journal Article · Tue Nov 10 00:00:00 EST 2020 · Metallomics · OSTI ID:1461295

Summers, Kelly L.; Dolgova, Natalia V.; Gagnon, Kenneth B.; +8 more

AS-2, a novel inhibitor of p53-dependent apoptosis, prevents apoptotic mitochondrial dysfunction in a transcription-independent manner and protects mice from a lethal dose of ionizing radiation

Journal Article · Fri Aug 08 00:00:00 EDT 2014 · Biochemical and Biophysical Research Communications · OSTI ID:1461295

Morita, Akinori; Ariyasu, Shinya; Wang, Bing; +9 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Zinc 8-hydroxyquinoline
Transient Absorption Spectroscopy
EXAFS
Density Functional Theory
DOSY NMR