Parisa Mehrkhodavandi

Last updated
Parisa Mehrkhodavandi
Alma mater University of British Columbia B.Sc. (1998)
Massachusetts Institute of Technology Ph.D. (2002)
Scientific career
Institutions University of British Columbia (2005-present)
California Institute of Technology (2002-2005)
Thesis Living α-olefin polymerization by cationic zirconium and hafnium complexes containing chelating diamidopyridine ligands  (2002)
Doctoral advisor Richard R. Schrock
Other academic advisors Chris Orvig, John E. Bercaw and Robert H. Grubbs

Parisa Mehrkhodavandi is a Canadian chemist and Professor of Chemistry at the University of British Columbia (UBC). [1] Her research focuses on the design of new catalysts that can effect polymerization of sustainably sourced or biodegradable polymers.

Contents

Education and training

Parisa Mehrkhodavandi completed her undergraduate degree in chemistry at the University of British Columbia in 1998. During her undergraduate, she worked with Prof. Chris Orvig on the synthesis of novel sugar-containing chelating ligands, [2] and studies on the binding of these ligands to transition metal ions. [3] Mehrkhodavandi also studied cationic lanthanide coordination complexes. [4]

Mehrkhodavandi pursued graduate studies at the Massachusetts Institute of Technology under the supervision of Richard R. Schrock. Her work at MIT focused on the synthesis of cationic zirconium and hafnium complexes bearing arylated diamidopyridine ligands, [5] and the polymerization of 1-hexene with these catalysts. [6] [7] [8] Mehrkhodavandi graduated with her Ph.D. in 2002.

She conducted a post-doctoral research stint at the California Institute of Technology working together with John E. Bercaw and Robert H. Grubbs. There, she studied the mechanism of a reaction of methanol to triptane with indium(III) iodide and zinc(II) iodide as catalysts. [9] [10]

Independent career

Mehrkhodavandi returned to the University of British Columbia as faculty in 2005 and was later promoted to associate professor in 2013.

Over her career, Mehrkhodavandi has been recognized with numerous awards, including but not limited to:

Research

Mehrkhodavandi is interested in developing catalysts that are highly active and enantioselective for the polymerization of lactide. Currently, catalysts for similar polymerizations must strike a balance between activity and enantioselectivity; the highly-active catalysts have poor enantioselectivity and vice versa. Highly active and enantioselective catalysts.png
Mehrkhodavandi is interested in developing catalysts that are highly active and enantioselective for the polymerization of lactide. Currently, catalysts for similar polymerizations must strike a balance between activity and enantioselectivity; the highly-active catalysts have poor enantioselectivity and vice versa.

Mehrkhodavandi’s research focuses on catalysis, where her group is pursuing new ligand design strategies. Her work has contributed to new synthetic routes for biodegradable polymers, [11] and fundamental insights into polymerization mechanisms. Her group has a specific interest in the formation of catalysts, such as chiral dinuclear indium complexes, that allow for enantioselective organic reactions. [12] [13] [14] [15] Mehrkhodavandi is also working on the development of biodegradable polyesters using these ligands using cyclic ester monomers. This is being done in three main ways: the first of which is the use of Lewis acid metal centers with chiral ligand supports to open cyclic lactones via ring-opening polymerizations. [16] [17] The second is the use of a chiral indium salen catalyst that allows for more precise iso-selectivity similar to chiral aluminum salen catalysts, but with higher activity than aluminum catalysts. The final method utilizes an ethoxy-bridged dinuclear indium catalyst [14] that allows for the creation of diblock copolymers due to its high activity and selective control.

Mehrkhodavandi has patented salen indium catalysts for the ring-opening polymerization of cyclic ester monomers like lactides. [18] [19] [20]

Mehrkhodavandi's research interests involve developing catalysts for ring-opening polymerizations. Ring-opening polymerizations involve opening up a ring-molecule via. nucleophillic attack to form a nucleophillic monomer, which can then continue the reaction to form a polymer. For different combinations of nucleophiles and rings, different catalysts are required. Dinuclear catalysts for controlled ring opening polymerization of cyclic esters.png
Mehrkhodavandi’s research interests involve developing catalysts for ring-opening polymerizations. Ring-opening polymerizations involve opening up a ring-molecule via. nucleophillic attack to form a nucleophillic monomer, which can then continue the reaction to form a polymer. For different combinations of nucleophiles and rings, different catalysts are required.

Publications

Mehrkhodavandi has published a significant amount of publications over her career. In recent works, Mehrkhodavandi writes about the role of the first alkoxide-bridged indium complex and the zinc analogues as important catalysts in the ring opening polymerization of lactides into polylactic acid. [12] The article pertains to how the indium complex bearing either the chiral or achiral ligand allows for the polymerization of racemic lactide into a highly heterotactic polylactic acid and how the indium complex along with the chiral ligand polymerizes meso-lactide into virtually atactic polylactic acid. Mehrkhodavandi discusses the mechanisms of these reactions in detail, along with the synthesis of the catalysts and activity of the resulting polymers. In another paper, Mehrkhodavandi writes about the use of an indium catalyst as a catalyst for lactide polymerization that has both high activity and high enantioselectivity - other lactide polymerizations feature either high activity or high enantioselectivity. [13] The results demonstrate site control as the primary factor behind the selectivity of the catalyst.

Related Research Articles

In polymer chemistry, living polymerization is a form of chain growth polymerization where the ability of a growing polymer chain to terminate has been removed. This can be accomplished in a variety of ways. Chain termination and chain transfer reactions are absent and the rate of chain initiation is also much larger than the rate of chain propagation. The result is that the polymer chains grow at a more constant rate than seen in traditional chain polymerization and their lengths remain very similar. Living polymerization is a popular method for synthesizing block copolymers since the polymer can be synthesized in stages, each stage containing a different monomer. Additional advantages are predetermined molar mass and control over end-groups.

<span class="mw-page-title-main">Michael addition reaction</span> Reaction in organic chemistry

In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor and a Michael acceptor to produce a Michael adduct by creating a carbon-carbon bond at the acceptor's β-carbon. It belongs to the larger class of conjugate additions and is widely used for the mild formation of carbon-carbon bonds.

<span class="mw-page-title-main">Olefin metathesis</span> Organic reaction involving the breakup and reassembly of alkene double bonds

In organic chemistry, olefin metathesis is an organic reaction that entails the redistribution of fragments of alkenes (olefins) by the scission and regeneration of carbon-carbon double bonds. Because of the relative simplicity of olefin metathesis, it often creates fewer undesired by-products and hazardous wastes than alternative organic reactions. For their elucidation of the reaction mechanism and their discovery of a variety of highly active catalysts, Yves Chauvin, Robert H. Grubbs, and Richard R. Schrock were collectively awarded the 2005 Nobel Prize in Chemistry.

<span class="mw-page-title-main">Hafnium tetrachloride</span> Chemical compound

Hafnium(IV) chloride is the inorganic compound with the formula HfCl4. This colourless solid is the precursor to most hafnium organometallic compounds. It has a variety of highly specialized applications, mainly in materials science and as a catalyst.

A carbometallation is any reaction where a carbon-metal bond reacts with a carbon-carbon π-bond to produce a new carbon-carbon σ-bond and a carbon-metal σ-bond. The resulting carbon-metal bond can undergo further carbometallation reactions or it can be reacted with a variety of electrophiles including halogenating reagents, carbonyls, oxygen, and inorganic salts to produce different organometallic reagents. Carbometallations can be performed on alkynes and alkenes to form products with high geometric purity or enantioselectivity, respectively. Some metals prefer to give the anti-addition product with high selectivity and some yield the syn-addition product. The outcome of syn and anti- addition products is determined by the mechanism of the carbometallation.

<span class="mw-page-title-main">Organozirconium and organohafnium chemistry</span>

Organozirconium chemistry is the science of exploring the properties, structure, and reactivity of organozirconium compounds, which are organometallic compounds containing chemical bonds between carbon and zirconium. Organozirconium compounds have been widely studied, in part because they are useful catalysts in Ziegler-Natta polymerization.

<span class="mw-page-title-main">2,2'-Bis(2-indenyl) biphenyl</span> Chemical compound

2,2′-Bis(2-indenyl) biphenyl is an organic compound with the formula [C6H4C9H7]2. The compound is the precursor, upon deprotonation, to ansa-metallocene complexes within the area of transition metal indenyl complexes.

Organogold chemistry is the study of compounds containing gold–carbon bonds. They are studied in academic research, but have not received widespread use otherwise. The dominant oxidation states for organogold compounds are I with coordination number 2 and a linear molecular geometry and III with CN = 4 and a square planar molecular geometry.

<span class="mw-page-title-main">Organomolybdenum chemistry</span> Chemistry of compounds with Mo-C bonds

Organomolybdenum chemistry is the chemistry of chemical compounds with Mo-C bonds. The heavier group 6 elements molybdenum and tungsten form organometallic compounds similar to those in organochromium chemistry but higher oxidation states tend to be more common.

<span class="mw-page-title-main">Metal salen complex</span> Coordination complex

A metal salen complex is a coordination compound between a metal cation and a ligand derived from N,N′-bis(salicylidene)ethylenediamine, commonly called salen. The classical example is salcomine, the complex with divalent cobalt Co2+, usually denoted as Co(salen). These complexes are widely investigated as catalysts and enzyme mimics.

<span class="mw-page-title-main">Trisoxazolines</span>

Trisoxazolines are a class of tridentate, chiral ligands composed of three oxazoline rings. Despite being neutral they are able to form stable complexes with high oxidation state metals, such as rare earths, due to the chelate effect. The ligands have been investigated for molecular recognition and their complexes are used in asymmetric catalysts and polymerisation.

<span class="mw-page-title-main">1,1-Dimethylethylenediamine</span> Chemical compound

1,1-Dimethylethylenediamine is the organic compound with the formula (CH3)2NCH2CH2NH2. It is a colorless liquid with a fishy odor, featuring one primary amine and a tertiary amine. It is used to prepare chelating diamine-containing ligands for the synthesis of metal catalysts. Additionally, it is a precursor to the drug chloropyramine.

Jenny Yue-fon Yang is an American chemist. She is a Professor of chemistry at the University of California, Irvine where she leads a research group focused on inorganic chemistry, catalysis, and solar fuels.

β-Carbon elimination is a type of reaction in organometallic chemistry wherein an allyl ligand bonded to a metal center is broken into the corresponding metal-bonded alkyl (aryl) ligand and an alkene. It is a subgroup of elimination reactions. Though less common and less understood than β-hydride elimination, it is an important step involved in some olefin polymerization processes and transition-metal-catalyzed organic reactions.

2-Methylthioethylamine is the organosulfur compound with the formula CH3SCH2CH2NH2. It is a colorless liquid. It can be viewed as the product of S-methylation of cysteamine or decarboxylation of S-methylcysteine. The compound is a ligand and, via Schiff base condensations, a ligand precursor.

<span class="mw-page-title-main">2-Hexyne</span> Chemical compound

2-Hexyne is an organic compound that belongs to the alkyne group. Just like its isomers, it also has the chemical formula of C6H10.

<span class="mw-page-title-main">Paula Diaconescu</span> Inorganic chemist

Paula L. Diaconescu is a Romanian-American chemistry professor at the University of California, Los Angeles. She is known for her research on the synthesis of redox active transition metal complexes, the synthesis of lanthanide complexes, metal-induced small molecule activation, and polymerization reactions. She is a fellow of the American Association for the Advancement of Science.

<span class="mw-page-title-main">Transition metal porphyrin complexes</span>

Transition metal porphyrin complexes are a family of coordination complexes of the conjugate base of porphyrins. Iron porphyrin complexes occur widely in Nature, which has stimulated extensive studies on related synthetic complexes. The metal-porphyrin interaction is a strong one such that metalloporphyrins are thermally robust. They are catalysts and exhibit rich optical properties, although these complexes remain mainly of academic interest.

In chemistry, a redox switch is a molecular device, which has two subunits, a functional component and a control component. The "control subunit" is redox-active, meaning that it can exist in either of two redox states. The "functional" component could have a variety of readouts, such as fluorescence, the binding of a substrate, or catalytic activity. The key feature of such redox switches is that the functional component is influenced by the control subunit. One of many examples of a redox switch consists of an anthracene substituent to a copper-thiacrown ether (14-ane-4) coordination complex. When in the cupric oxidation state, the anthracene does not fluoresce. When in the cuprous state, the assembly is highly fluorescent. Several redox switches have been produced from ferrocenecarboxylic acid, which can be conjugated to a number of functional components. 1,1'-Diaminoferrocene has been incorporated into various diamide and diimine ligands, which form catalysts that exhibit redox switching.

1,1'-Diaminoferrocene is the organoiron compound with the formula Fe(C5H4NH2)2. It is the simplest diamine derivative of ferrocene. It is a yellow, air-sensitive solid that is soluble in aqueous acid. The 1,1' part of its name refers to the location of the amine groups on separate rings. Compared to the parent ferrocene, the diamine is about 600 mV more reducing.

References

  1. ↑ "Parisa Mehrkhodavandi | UBC Chemistry". www.chem.ubc.ca. Retrieved 2021-06-10.
  2. ↑ Yano, Shigenobu; Shinohara, Yoshie; Mogami, Kaoru; Yokoyama, Mika; Tanase, Tomoaki; Sakakibara, Toru; Nishida, Fumiko; Mochida, Kenichi; Kinoshita, Isamu; Doe, Matsumi; Ichihara, Kanako (2003-05-01). "General Synthesis of Useful Chelating Reagents Having a Sugar Unit, 1,3-Diamino-2-propyl β-D-Glucopyranoside and 1,3-Diamino-2-propyl α-D-Mannopyranoside". Chemistry Letters. 28 (3): 255–256. doi:10.1246/cl.1999.255.
  3. ↑ Song, Bin; Mehrkhodavandi, Parisa; Buglyó, Péter; Mikata, Yuji; Shinohara, Yoshie; Yoneda, Kazumi; Yano, Shigenobu; Orvig, Chris (2000-01-01). "Acid–base and metal ion-binding properties of diaminopropyl D-glucopyranoside and diaminopropyl D-mannopyranoside compounds in aqueous solution". Journal of the Chemical Society, Dalton Transactions (8): 1325–1333. doi:10.1039/A908384G. ISSN   1364-5447.
  4. ↑ Caravan, P.; Mehrkhodavandi, Parisa; Orvig, Chris (1997-03-01). "Cationic Lanthanide Complexes of N,N'-Bis(2-pyridylmethyl)ethylenediamine-N,N'-diacetic Acid (H2bped)". Inorganic Chemistry. 36 (7): 1316–1321. doi:10.1021/ic9613016. ISSN   0020-1669. PMID   11669707.
  5. ↑ Mehrkhodavandi, Parisa; Schrock, Richard R.; Bonitatebus, Peter J. (2002-12-01). "Synthesis and Structures of Zirconium and Hafnium Alkyl Complexes That Contain [H3CC(2-C5H4N)(CH2NAr)2]2- ([ArNpy]2-; Ar = Mesityl, Triisopropylphenyl) Ligands". Organometallics. 21 (26): 5785–5798. doi:10.1021/om0207055. ISSN   0276-7333.
  6. ↑ Mehrkhodavandi, Parisa; Bonitatebus, Peter J.; Schrock, Richard R. (2000-08-01). "A Comparison of Cationic Zirconium Methyl and Isobutyl Initiators that Contain an Arylated Diamido-Pyridine Ligand for Polymerization of 1-Hexene. Elucidation of a Dramatic "Initiator Effect"". Journal of the American Chemical Society. 122 (32): 7841–7842. doi:10.1021/ja000772v. ISSN   0002-7863.
  7. ↑ Mehrkhodavandi, Parisa; Schrock, Richard R. (2001-10-31). "Cationic Hafnium Alkyl Complexes that Are Stable toward β-Hydride Elimination below 10 °C and Active as Initiators for the Living Polymerization of 1-Hexene". Journal of the American Chemical Society. 123 (43): 10746–10747. doi:10.1021/ja0114198. ISSN   0002-7863. PMID   11674011.
  8. ↑ Mehrkhodavandi, Parisa; Schrock, Richard R.; Pryor, Lara L. (2003-10-03). "Living Polymerization of 1-Hexene by Cationic Zirconium and Hafnium Complexes that Contain a Diamido/Donor Ligand of the Type [H3CC(2-C5H4N)(CH2NMesityl)2]2-. A Comparison of Methyl and Isobutyl Initiators". Organometallics. 22 (22): 4569–4583. doi:10.1021/om030438i. ISSN   0276-7333.
  9. ↑ Bercaw, John E.; Diaconescu, Paula L.; Grubbs, Robert H.; Hazari, Nilay; Kay, Richard D.; Labinger, Jay A.; Mehrkhodavandi, Parisa; Morris, George E.; Sunley, Glenn J.; Vagner, Patrick (2007-11-30). "Conversion of Methanol to 2,2,3-Trimethylbutane (Triptane) over Indium(III) Iodide". Inorganic Chemistry. 46 (26): 11371–11380. doi:10.1021/ic7014447. ISSN   0020-1669. PMID   18047325.
  10. ↑ Bercaw, John E.; Diaconescu, Paula L.; Grubbs, Robert H.; Kay, Richard D.; Kitching, Sarah; Labinger, Jay A.; Li, Xingwei; Mehrkhodavandi, Parisa; Morris, George E.; Sunley, Glenn J.; Vagner, Patrick (2006-10-19). "On the Mechanism of the Conversion of Methanol to 2,2,3-Trimethylbutane (Triptane) over Zinc Iodide". The Journal of Organic Chemistry. 71 (23): 8907–8917. doi:10.1021/jo0617823. ISSN   0022-3263. PMID   17081022.
  11. ↑ Xu, Cuiling; Yu, Insun; Mehrkhodavandi, Parisa (2012-06-12). "Highly controlled immortal polymerization of β-butyrolactone by a dinuclear indium catalyst". Chemical Communications. 48 (54): 6806–6808. doi:10.1039/C2CC33114D. ISSN   1364-548X. PMID   22669203.
  12. 1 2 Kremer, Alexandre B.; Osten, Kimberly M.; Yu, Insun; Ebrahimi, Tannaz; Aluthge, Dinesh C.; Mehrkhodavandi, Parisa (2016-06-06). "Dinucleating Ligand Platforms Supporting Indium and Zinc Catalysts for Cyclic Ester Polymerization". Inorganic Chemistry. 55 (11): 5365–5374. doi:10.1021/acs.inorgchem.6b00358. ISSN   0020-1669. PMID   27187767.
  13. 1 2 Aluthge, Dinesh C.; Patrick, Brian O.; Mehrkhodavandi, Parisa (2013-04-19). "A highly active and site selective indium catalyst for lactide polymerization". Chemical Communications. 49 (39): 4295–4297. doi:10.1039/C2CC33519K. ISSN   1364-548X. PMID   22729290.
  14. 1 2 Osten, Kimberly M.; Yu, Insun; Duffy, Ian R.; Lagaditis, Paraskevi O.; Yu, Joey C.-C.; Wallis, Christopher J.; Mehrkhodavandi, Parisa (2012-06-15). "Effects of ligand tuning on dinuclear indium catalysts for lactide polymerization". Dalton Transactions. 41 (26): 8123–8134. doi:10.1039/C2DT30148B. ISSN   1477-9234. PMID   22481250.
  15. ↑ Douglas, Amy F.; Patrick, Brian O.; Mehrkhodavandi, Parisa (2008). "A Highly Active Chiral Indium Catalyst for Living Lactide Polymerization". Angewandte Chemie International Edition. 47 (12): 2290–2293. doi: 10.1002/anie.200705033 . ISSN   1521-3773. PMID   18273846.
  16. ↑ Broderick, Erin M.; Guo, Neng; Vogel, Carola S.; Xu, Cuiling; Sutter, Jörg; Miller, Jeffrey T.; Meyer, Karsten; Mehrkhodavandi, Parisa; Diaconescu, Paula L. (2011-06-22). "Redox Control of a Ring-Opening Polymerization Catalyst". Journal of the American Chemical Society. 133 (24): 9278–9281. doi:10.1021/ja2036089. ISSN   0002-7863. PMID   21604745.
  17. ↑ Wang, Xinke; Thevenon, Arnaud; Brosmer, Jonathan L.; Yu, Insun; Khan, Saeed I.; Mehrkhodavandi, Parisa; Diaconescu, Paula L. (2014-08-13). "Redox Control of Group 4 Metal Ring-Opening Polymerization Activity toward l-Lactide and ε-Caprolactone". Journal of the American Chemical Society. 136 (32): 11264–11267. doi:10.1021/ja505883u. ISSN   0002-7863. PMID   25062499. S2CID   22098566.
  18. ↑ US 9777023,Mehrkhodavandi, Parisa; Yu, Insun& Acosta-Ramirez, J. Alberto,"Dinuclear indium catalysts and their use for (Co)polymerization of cyclic esters",published 2017-10-03, assigned to University of British Columbia
  19. ↑ USapplication 20150018493,Mehrkhodavandi, Parisa; Aluthge, Dinesh C.& Clark, Timothy Jameset al.,"Salen indium catalysts and methods of manufacture and use thereof",published 2015-01-15, assigned to Greencentre Canada and University of British Columbia , now abandoned.
  20. ↑ US 10280185,Mehrkhodavandi, Parisa&Aluthge, Dinesh C.,"Mononuclear salen indium catalysts and methods of manufacture and use thereof",published 2019-05-07, assigned to University of British Columbia
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.