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Professor James Crowley

james_crowleyPhD(Chicago) MSc(Well)

Tel +64 3 479 7731
Location Science II, 2n10
Email jcrowley@chemistry.otago.ac.nz

For more information about the Crowley Research Group: http://blogs.otago.ac.nz/jamescrowley

Employment History and Qualifications

Professor, University of Otago 2015–
Senior Lecturer, University of Otago 2011-2015
Lecturer, University of Otago 2008–2011
British Ramsay Memorial Postdoctoral Fellow (with Prof. D. A. Leigh, FRS), University of Edinburgh 2006–2007
Postdoctoral Fellow (with Prof. D. A. Leigh, FRS), University of Edinburgh 2005–2006
S.M and Ph.D, The University of Chicago (Prof. B Bosnich, FRS) 2000-2005
B.Sc. (Hons) and M.Sc., Victoria University of Wellington (Dr. D. C. Weatherburn) 1994-1999


Awards and Distinctions

University of Otago, Division of Sciences Research Group of the Year 2016
Royal Australian Chemical Institute (RACI), Organometallic Chemistry Award 2015
Finalist in OUSA Supervisor of the Year Awards 2015
Chemical Society of Japan (CSJ) Asian International Distinguished Lectureship Award 2015
Royal Australian Chemical Institute (RACI), Alan Sargeson Lectureship 2014
Royal Society of Chemistry/New Zealand Institute of Chemistry Easterfield Award 2013
University of Otago Early Career Award for Distinction in Research 2011
British Ramsay Memorial Fellowship (U of Ed.) 2006-2008
Joan Shiu Award for Student Service, (U of C) 2004
Curtis-Gordon Scholarship for Chemistry (VUW) 1998

Relevant Disciplines

Organic / Inorganic / Organometallic / Materials / Supramolecular Chemistry / Nanoscience

My research interests are in synthetic organic, inorganic, organometallic and supramolecular chemistry. I am interested in the design and synthesis of new functional materials. I have expertise in a wide range of synthetic and spectroscopic techniques including NMR, IR, UV-vis and X-ray crystallography. Major areas of interest include:

CuAAC “Click” coordination chemistry. The mild and modular Cu(I)-catalyzed 1,3-cycloaddition of terminal alkynes with organic azides (the CuAAC “click” reaction) allows the ready formation of functionalised 1,4-disubstituted-1,2,3-triazole scaffolds and this has led to an explosion of interest in the coordination chemistry of these heterocycles. A diverse array of mono-, bi-, tri- and polydentate ligands incorporating 1,4-disubstituted-1,2,3-triazole units have been synthesised and characterised. Easy access to readily functionalised ligand architectures is of crucial importance in a range of different areas and we are exploiting these ligands for the development of new catalysts, metallo-pharmaceuticals, bio-imaging agents, metallosupramolecular architectures, and molecular machines.

Synthetic molecular machines (nanotechnology). It is well established that the fundamental processes of life at the cellular level are governed by complex biological molecular machines which convert chemical energy into work. My research group is interested in exploiting a range of interlocked and non-interlocked molecular architectures for the development of synthetic molecular machines. These efforts are motivated by the goal of creating synthetic devices or materials that, like their far more complex biological counterparts, could carry out tasks by exploiting controlled molecular-level mechanical motion; a key requirement for the development of useable nanotechnology.

Functional metallosupramolecular architectures. I am also interested in the engineering of functional molecular architectures via self-assembly. In particular we are attempting to exploit these self-assembled cages as novel metallo-pharmaceuticals, for drug delivery and as nanoreactors for carrying out chemical transformations.

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Publications

Lagesse, N. R., Tan, K. Y. L., Crowley, J. D., & Findlay, J. A. (2020). Planar 2-pyridyl-1,2,3-triazole derived metallo-ligands: Self-assembly with PdCl2 and photocatalysis. Chemistry: An Asian Journal, 15, 1567-1573. doi: 10.1002/asia.202000284

McNeill, S., Giles, N. M., Preston, D., Jones, P. P., Crowley, J. D., & Giles, G. I. (2020). The quadruply stranded metallo-supramolecular helicate [Pd2 (hextrz)4]4+ acts as a molecular mimic of cytolytic peptides. Chemical Research in Toxicology, 33, 1822-1834. doi: 10.1021/acs.chemrestox.0c00061

Crlikova, H., Malina, J., Novohradsky, V., Kostrhunova, H., Vasdev, R. A. S., Crowley, J. D., … Brabec, V. (2020). Antiproliferative activity and associated DNA interactions of [Co2L3]6+ cylinders derived from bis(bidentate) 2-pyridyl-1,2,3-triazole ligands. Organometallics, 39, 1448-1455. doi: 10.1021/acs.organomet.0c00146

Lisboa, L. S., Findlay, J. A., Wright, L. J., Hartinger, C. G., & Crowley, J. D. (2020). A reduced-symmetry heterobimetallic [PdPtL4]4+ cage: Assembly, guest binding, and stimulus-induced switching. Angewandte Chemie International Edition, 59, 11101-11107. doi: 10.1002/anie.202003220

Shillito, G. E., Preston, D., Traber, P., Steinmetzer, J., McAdam, C. J., Crowley, J. D., … Gordon, K. C. (2020). Excited-state switching frustrates the tuning of properties in triphenylamine-donor-ligand rhenium(I) and platinum(II) complexes. Inorganic Chemistry, 59, 6736-6746. doi: 10.1021/acs.inorgchem.9b03691

Chapter in Book - Research

Crowley, J. D., & McMorran, D. A. (2012). "Click triazole" Coordination chemistry: Exploiting 1,4-disubstituted-1,2,3-triazoles as ligands. In J. Košmrlj (Ed.), Click triazoles: Topics in heterocyclic chemistry (Vol. 28). (pp. 31-83). Berlin, Germany: Springer. doi: 10.1007/7081_2011_67

Crowley, J. D., Kilpin, K. J., & Keep, C. C. (2011). Exploiting ferrocene to develop synthetic molecular machines. In E. S. Phillips (Ed.), Ferrocenes: Compounds, properties and applications. (pp. 149-188). New York: Nova Science.

Crowley, J. D., Kay, E. R., & Leigh, D. A. (2008). Chemically driven artificial molecular machines. In M. Shahinpoor & H.-J. Schneider (Eds.), Intelligent materials. (pp. 1-47). Cambridge, UK: Royal Society of Chemistry.

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Journal - Research Article

Lagesse, N. R., Tan, K. Y. L., Crowley, J. D., & Findlay, J. A. (2020). Planar 2-pyridyl-1,2,3-triazole derived metallo-ligands: Self-assembly with PdCl2 and photocatalysis. Chemistry: An Asian Journal, 15, 1567-1573. doi: 10.1002/asia.202000284

Shillito, G. E., Preston, D., Traber, P., Steinmetzer, J., McAdam, C. J., Crowley, J. D., … Gordon, K. C. (2020). Excited-state switching frustrates the tuning of properties in triphenylamine-donor-ligand rhenium(I) and platinum(II) complexes. Inorganic Chemistry, 59, 6736-6746. doi: 10.1021/acs.inorgchem.9b03691

Lisboa, L. S., Findlay, J. A., Wright, L. J., Hartinger, C. G., & Crowley, J. D. (2020). A reduced-symmetry heterobimetallic [PdPtL4]4+ cage: Assembly, guest binding, and stimulus-induced switching. Angewandte Chemie International Edition, 59, 11101-11107. doi: 10.1002/anie.202003220

Crlikova, H., Malina, J., Novohradsky, V., Kostrhunova, H., Vasdev, R. A. S., Crowley, J. D., … Brabec, V. (2020). Antiproliferative activity and associated DNA interactions of [Co2L3]6+ cylinders derived from bis(bidentate) 2-pyridyl-1,2,3-triazole ligands. Organometallics, 39, 1448-1455. doi: 10.1021/acs.organomet.0c00146

McNeill, S., Giles, N. M., Preston, D., Jones, P. P., Crowley, J. D., & Giles, G. I. (2020). The quadruply stranded metallo-supramolecular helicate [Pd2 (hextrz)4]4+ acts as a molecular mimic of cytolytic peptides. Chemical Research in Toxicology, 33, 1822-1834. doi: 10.1021/acs.chemrestox.0c00061

Barnsley, J. E., Findlay, J. A., Shillito, G. E., Pelet, W. S., Scottwell, S. Ø., McIntyre, S. M., Tay, E. J., Gordon, K. C., & Crowley, J. D. (2019). Long-lived MLCT states for Ru(II) complexes of ferrocene-appended 2,2'-bipyridines. Dalton Transactions, 48, 15713-15722. doi: 10.1039/c9dt02025j

van Hilst, Q. V. C., Vasdev, R. A. S., Preston, D., Findlay, J. A., Scottwell, S. Ø., Giles, G. I., Brooks, H. J. L., & Crowley, J. D. (2019). Synthesis, characterisation and antimicrobial studies of some 2,6-bis(1,2,3-triazol-4-yl)pyridine ruthenium(II) “click” complexes. Asian Journal of Organic Chemistry, 8, 496-505. doi: 10.1002/ajoc.201900088

Preston, D., Inglis, A. R., Crowley, J. D., & Kruger, P. E. (2019). Self-assembly and cycling of a three-state PdxLy metallosupramolecular system. Chemistry: An Asian Journal, 14, 3404-3408. doi: 10.1002/asia.201901238

Mapley, J. I., Ross, D. A. W., McAdam, C. J., Gordon, K. C., & Crowley, J. D. (2019). Triphenylamine-substituted 2-pyridyl-1,2,3-triazole copper(I) complexes: An experimental and computational investigation. Journal of Coordination Chemistry, 72(8), 1378-1394. doi: 10.1080/00958972.2019.1593388

Preston, D., Findlay, J. A., & Crowley, J. D. (2019). Recognition properties and self-assembly of planar [M(2-pyridyl-1,2,3-triazole)2]2+ metallo-ligands. Chemistry: An Asian Journal, 14, 1136-1142. doi: 10.1002/asia.201801132

van Hilst, Q. V. C., Lagesse, N. R., Preston, D., & Crowley, J. D. (2018). Functional metal complexes from CuAAC "click" bidentate and tridentate pyridyl-1,2,3-triazole ligands. Dalton Transactions, 4, 997-1002. doi: 10.1039/c7dt04570k

Preston, D., Gordon, K. C., Sutton, J. J., & Crowley, J. D. (2018). A nona-nuclear heterometallic Pd3Pt6 "Donut" shaped cage: Molecular recognition and photocatalysis. Angewandte Chemie International Edition, 57(28), 8659-8663. doi: 10.1002/anie.201804745

Findlay, J. A., Barnsley, J. E., Gordon, K. C., & Crowley, J. D. (2018). Synthesis and light-induced actuation of photo-labile 2-pyridyl-1,2,3-triazole Ru(bis-bipyridyl) appended rerrocene rotors. Molecules, 23(8), 2037. doi: 10.3390/molecules23082037

Findlay, J. A., McAdam, C. J., Sutton, J. J., Preston, D., Gordon, K. C., & Crowley, J. D. (2018). Metallosupramolecular architectures formed with ferrocene-linked bis-bidentate ligands: Synthesis, structures, and electrochemical studies. Inorganic Chemistry, 57(7), 3602-3614. doi: 10.1021/acs.inorgchem.7b02503

Vasdev, R. A. S., Gaudin, L. F., Preston, D., Jogy, J. P., Giles, G. I., & Crowley, J. D. (2018). Anticancer activity and cisplatin binding ability of bis-quinoline and bis-isoquinoline derived Pd2L44+ metallosupramolecular cages. Frontiers in Chemistry, 6, 563. doi: 10.3389/fchem.2018.00563

Shillito, G. E., Hall, T. B. J., Preston, D., Traber, P., Wu, L., Reynolds, K. E. A., … Lucas, N. T., Crowley, J. D., … Gordon, K. C. (2018). Dramatic alteration of 3ILCT lifetimes using ancillary ligands in [Re(L)(CO)3(phen-TPA)]n+ complexes: An integrated spectroscopic and theoretical study. Journal of the American Chemical Society, 140(13), 4534-4542. doi: 10.1021/jacs.7b12868

Scottwell, S. Ø., Barnsley, J. E., McAdam, C. J., Gordon, K. C., & Crowley, J. D. (2017). A ferrocene based switchable molecular folding ruler. Chemical Communications, 53, 7628-7631. doi: 10.1039/C7CC03358C

Vasdev, R. A. S., Preston, D., & Crowley, J. D. (2017). Multicavity metallosupramolecular architectures. Chemistry: An Asian Journal, 12(19), 2513-2523. doi: 10.1002/asia.201700948

Ross, D. A. W., Preston, D., & Crowley, J. D. (2017). Self-Assembly with 2,6-Bis(1-(pyridin-4-ylmethyl)-1H-1,2,3-triazol-4-yl)pyridine: Silver(I) and Iron(II) Complexes. Molecules, 22(10), 1762. doi: 10.3390/molecules22101762

Kim, T. Y., Digal, L., Gardiner, M. G., Lucas, N. T., & Crowley, J. D. (2017). Octahedral [Pd6L8]12+ metallosupramolecular cages: Synthesis, structures and guest-encapsulation studies. Chemistry: A European Journal, 23, 15089-15097. doi: 10.1002/chem.201702518

Preston, D., Lewis, J. E. M., & Crowley, J. D. (2017). Multicavity [PdnL4]2n+ cages with controlled segregated binding of different guests. Journal of the American Chemical Society, 139(6), 2379-2386. doi: 10.1021/jacs.6b11982

Preston, D., White, K. F., Lewis, J. E. M., Vasdev, R. A. S., Abrahams, B. F., & Crowley, J. D. (2017). Solid state gas adsorption studies with discrete palladium(II) [Pd2(L)4]4+ cages. Chemistry: A European Journal, 23(44), 10559-10567. doi: 10.1002/chem.201701477

Vasdev, R. A. S., Preston, D., & Crowley, J. D. (2017). Functional metallosupramolecular architectures using 1,2,3-triazole ligands: It's as easy as 1,2,3 "click". Dalton Transactions, 46(8), 2402-2414. doi: 10.1039/c6dt04702e

Scottwell, S. Ø., & Crowley, J. D. (2016). Ferrocene-containing non-interlocked molecular machines. Chemical Communications, 52, 2451-2464. doi: 10.1039/c5cc09569g

Kumar, S. V., Scottwell, S. Ø., Waugh, E., McAdam, C. J., Hanton, L. R., Brooks, H. J. L., & Crowley, J. D. (2016). Antimicrobial properties of tris(homoleptic) ruthenium(II) 2-pyridyl-1,2,3-triazole "click" complexes against pathogenic bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). Inorganic Chemistry, 55(19), 9767-9777. doi: 10.1021/acs.inorgchem.6b01574

Elliott, A. B. S., Lewis, J. E. M., van der Salm, H., McAdam, C. J., Crowley, J. D., & Gordon, K. C. (2016). Luminescent cages: Pendant emissive units on [Pd2L4]4+ "click" cages. Inorganic Chemistry, 55(7), 3440-3447. doi: 10.1021/acs.inorgchem.5b02843

Preston, D., Barnsley, J. E., Gordon, K. C., & Crowley, J. D. (2016). Controlled formation of heteroleptic [Pd2(La)2(Lb)2]4+ cages. Journal of the American Chemical Society, 138(33), 10578-10585. doi: 10.1021/jacs.6b05629

Pages, B. J., Sakoff, J., Gilbert, J., Zhang, Y., Li, F., Preston, D., Crowley, J. D., & Aldrich-Wright, J. R. (2016). Investigating the cytotoxicity of platinum(II) complexes incorporating bidentate pyridyl-1,2,3-triazole “click” ligands. Journal of Inorganic Biochemistry, 165, 92-99. doi: 10.1016/j.jinorgbio.2016.06.017

Preston, D., Tucker, R. A. J., Garden, A. L., & Crowley, J. D. (2016). Heterometallic [MnPtn(L)2n]x+ macrocycles from dichloromethane-derived bis-2-pyridyl-1,2,3-triazole ligands. Inorganic Chemistry, 55(17), 8928-8934. doi: 10.1021/acs.inorgchem.6b01435

Huff, G. S., Lo, W. K. C., Horvath, R., Turner, J. O., Sun, X.-Z., Weal, G. R., Davidson, H. J., Kennedy, A. D. W., McAdam, C. J., Crowley, J. D., … Gordon, K. C. (2016). Excited states of triphenylamine-substituted 2-pyridyl-1,2,3-triazole complexes. Inorganic Chemistry, 55(23), 12238-12253. doi: 10.1021/acs.inorgchem.6b01959

Vasdev, R. A. S., Preston, D., Scottwell, S. Ø., Brooks, H. J. L., Crowley, J. D., & Schramm, M. P. (2016). Oxidatively locked [Co2L3]6+ cylinders derived from bis(bidentate) 2-Pyridyl-1,2,3-triazole "Click" ligands: Synthesis, stability, and antimicrobial studies. Molecules, 21(11), 1548. doi: 10.3390/molecules21111548

McKay, A. P., Lo, W. K. C., Preston, D., Giles, G. I., Crowley, J. D., Barnsley, J. E., Gordon, K. C., & McMorran, D. A. (2016). Palladium(II) and platinum(II) complexes of ((2-pyridyl)pyrazol-1-ylmethyl)benzoic acids: Synthesis, solid state characterisation and biological cytotoxicity. Inorganica Chimica Acta, 446, 41-53. doi: 10.1016/j.ica.2016.02.038

Preston, D., McNeill, S. M., Lewis, J. E. M., Giles, G. I., & Crowley, J. D. (2016). Enhanced kinetic stability of [Pd2L4] 4+ cages through ligand substitution. Dalton Transactions, 45, 8050-8060. doi: 10.1039/c6dt00133e

Wright, J. R., Crowley, J. D., & Lucas, N. T. (2016). Carbon-rich "click" 1,2,3-triazoles: Hexaphenylbenzene and hexa-peri-hexabenzocoronene-based ligands for Suzuki-Miyaura catalysts. Chemical Communications, 52(88), 12976-12979. doi: 10.1039/c6cc07413h

Barnsley, J. E., Scottwell, S. Ø., Elliott, A. B. S., Gordon, K. C., & Crowley, J. D. (2016). Structural, electronic, and computational studies of heteroleptic Cu(I) complexes of 6,6′-dimesityl-2,2′-bipyridine with ferrocene-appended ethynyl-2,2′-bipyridine ligands. Inorganic Chemistry, 55(16), 8184-8192. doi: 10.1021/acs.inorgchem.6b01300

Lo, W. K. C., Castillo, C. E., Gueret, R., Fortage, J., Rebarz, M., Sliwa, M., … McAdam, C. J., … McMorran, D. A., Crowley, J. D., … Blackman, A. G. (2016). Synthesis, characterization, and photocatalytic H2-evolving activity of a family of [Co(N4Py)(X)]n+ complexes in aqueous solution. Inorganic Chemistry, 55, 4564-4581. doi: 10.1021/acs.inorgchem.6b00391

McNeill, S. M., Preston, D., Lewis, J. E. M., Robert, A., Knerr-Rupp, K., Graham, D. O., Wright, J. R., Giles, G. I., & Crowley, J. D. (2015). Biologically active [Pd2L4]4+ quadruply-stranded helicates: Stability and cytotoxicity. Dalton Transactions, 44, 11129-11136. doi: 10.1039/c5dt01259g

Preston, D., Fox-Charles, A., Lo, W. K. C., & Crowley, J. D. (2015). Chloride triggered reversible switching from a metallosupramolecular [Pd2L4]4+ cage to a [Pd2L2Cl4] metallo-macrocycle with release of endo- and exo-hedrally bound guests. Chemical Communications, 51, 9042-9045. doi: 10.1039/C5CC02226F

Lo, W. K. C., McAdam, C. J., Blackman, A. G., Crowley, J. D., & McMorran, D. A. (2015). The pentadentate ligands 2PyN2Q and N4Py, and their Cu(II) and Zn(II) complexes: A synthetic, spectroscopic and crystallographic structural study. Inorganica Chimica Acta, 426, 183-194. doi: 10.1016/j.ica.2014.11.036

Kumar, S. V., Lo, W. K. C., Brooks, H. J. L., & Crowley, J. D. (2015). Synthesis, structure, stability and antimicrobial activity of a ruthenium(II) helicate derived from a bis-bidentate "click" pyridyl-1,2,3-triazole ligand. Inorganica Chimica Acta, 425, 1-6. doi: 10.1016/j.ica.2014.10.011

Scottwell, S. Ø., Elliott, A. B. S., Shaffer, K. J., Nafady, A., McAdam, C. J., Gordon, K. C., & Crowley, J. D. (2015). Chemically and electrochemically induced expansion and contraction of a ferrocene rotor. Chemical Communications, 51, 8164. doi: 10.1039/c5cc01973g

Lo, W. K. C., Huff, G. S., Preston, D., McMorran, D. A., Giles, G. I., Gordon, K. C., & Crowley, J. D. (2015). A dinuclear platinum(II) N4Py complex: An unexpected coordination mode for N4Py. Inorganic Chemistry, 54(14), 6671-6673. doi: 10.1021/acs.inorgchem.5b01032

Cubanski, J. R., Reish, M. E., Blackman, A. G., Steel, P. J., Gordon, K. C., McMorran, D. A., & Crowley, J. D. (2015). Hybrid pyrazolyl-1,2,3-triazolyl tripodal tetraamine ligands: Click synthesis and cobalt(III) complexes. Australian Journal of Chemistry, 68(7), 1160-1170. doi: 10.1071/CH14700

Kim, T. Y., Lucas, N. T., & Crowley, J. D. (2015). A diaryl-linked [Pd2L4]4+ metallosupramolecular architecture: Synthesis, structures and cisplatin binding studies. Supramolecular Chemistry, 27(11-12), 734-745. doi: 10.1080/10610278.2015.1063633

Noor, A., Maloney, D. L., Lewis, J. E. M., Lo, W. K. C., & Crowley, J. D. (2015). Acid–base driven ligand exchange with palladium(II) "click" complexes. Asian Journal of Organic Chemistry, 4(3), 208-211. doi: 10.1002/ajoc.201402197

Lo, W. K. C., Huff, G. S., Cubanski, J. R., Kennedy, A. D. W., McAdam, C. J., McMorran, D. A., Gordon, K. C., & Crowley, J. D. (2015). Comparison of inverse and regular 2-pyridyl-1,2,3-triazole "click" complexes: Structures, stability, electrochemical, and photophysical properties. Inorganic Chemistry, 54(4), 1572-1587. doi: 10.1021/ic502557w

Noor, A., Lo, W. K. C., Moratti, S. C., & Crowley, J. D. (2014). CuAAC "click" active-template synthesis of functionalised [2]rotaxanes using small exo-substituted macrocycles: How small is too small? Chemical Communications, 50, 7044-7047. doi: 10.1039/c4cc03077j

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