Goldup, Stephen - University of Birmingham

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University of Birmingham School of Chemistry
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个人简介

Steve obtained an MChem degree from the University of Oxford where he began his research career with a Part II project in the group of Sir Prof. Jack Baldwin. He continued his research training with a PhD in natural product synthesis under the supervision of Prof. Tony Barrett before shifting focus to apply his synthetic skills to the realisation of mechanically interlocked non-natural products during post doctoral work with Prof. David Leigh at the University of Edinburgh where in 2007 he was appointed as Fixed Term Lecturer in Organic Chemistry. In 2008 he moved to Queen Mary with the award of a Leverhulme Trust Early Career Fellowship and in October 2009 he was awarded a Royal Society University Research Fellowship. In October 2014 the group moved to the University of Southampton where Steve took up the position of Associate Professor. In August 2017, Steve was promoted to Professor of Chemistry. Research in the Goldup Group focusses on the synthesis of novel mechanically interlocked molecules and their application as sensors, catalysts and materials. Esteem, Leadership and Prizes 2020 UK Blavatnik Young Scientist Awards Finalist Royal Society Wolfson Research Fellowship 2019 – 2024 Associate Editor for Chemical Science In the top 5% of reviewers for Angew. Chem. Int. Ed. One of the “top 10 reviewers” for Chem. Soc. Rev. 2016 – see here. Co-chair of the 2019 Gordon Research Conference on Artificial Molecular Switches & Motors Invited lecture at the 2nd Telleuride Workshop on Molecular Rotors, Motors, and Switches Royal Society of Chemistry Hickinbottom Award 2014 for “pioneering work on the synthesis of rotaxanes“. Invited Feature Article for Chem. Commun. 2014 Emerging Investigator Issue. Invited oral presentation at the Transatlantic Frontiers of Chemistry (2013), an international (UK, US, Brazil, Germany) interdisciplinary meeting for emerging leaders in the chemical sciences. Organised the Royal Society of Chemistry Macrocyclic and Supramolecular Chemistry meeting 2012. Dave Hill Cup at Gregynog Synthesis Meeting, 2012. Member of the advisory board for Chem. Soc. Rev. (2012 onwards). Thieme Journal Chemistry Award 2012. Taylor & Francis Poster Prize for Innovation in Supramolecular Chemistry 2009.

研究领域

Applications of Mechanically Interlocked Molecules Our general research focus is on the synthesis and applications of mechanically interlocked molecules such as rotaxanes (an example of which is shown in the centre on the right) and catenanes. These challenging molecules have been shown to have potential applications in catalysis, drug delivery, electronic materials and sensing. We also investigate new synthetic methods and the underlying mechanism of organic reactions in order to develop molecular machines which carry out synthetic tasks to produce novel materials that are extremely hard to access in other ways – a trick we know can be used to great effect as many such devices are found in living cells! Size Matters: Active template synthesis of functional interlocked molecules The active template approach to mechanically interlocked molecules is a versatile and powerful method for synthesising catenanes and rotaxanes which are impossible to form using other methods and the first approach capable of operating with substochiometric quantities of template. Mechanical Bonding to Stabilise Reactive Intermediates – a Stable Cu(I) Organometallic We have recently extended our small macrocycle AT-CuAAC methodology to the synthesis of a sterically protected Cu(I)-organometallic which survives column chromatography and aqueous work up. It can even be synthesised under aqueous conditions! This is only the second example of an isolated Cu-triazolide and the first to display this level of stability. This further demonstrates the potential of the mechanical bond to stabilise reactive species and we are currently investigating the properties of these extremely unusual copper complexes. Mechanically Chiral Rotaxanes Interlocked structures such as catenanes, rotaxanes and knots can display molecular asymmetry as a direct result of the mechanical bond. However, relatively few such molecules have been isolated enantiopure because the methods needed to produce them (usually chiral stationary phase HPLC) are not suited to large scale investigations. We recently demonstrate the first scalable synthesis of mechanically planar chiral rotaxanes in high enantiopurity, using a “chiral auxiliary” type approach: the AT-CuAAC reaction using a covalently chiral stopper was used to synthesise and separate mechanical diastereomers that differ only in the orientation of the macrocycle. Subsequent cleavage of the auxiliary from the separated diastereoisomers led to mechanically chiral rotaxanes in >99% ee. We are now working to extend this approach to other active template reactions and investigate the properties of this newly accesible form of molecular asymmetry.

近期论文

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Off Detailed Balance: Non-Equilibrium Steady States in Catalysis, Molecular Motors and Supramolecular Materials Ivan Aprahamian,* Stephen M. Goldup,* 2023 Direct Detection of Hydrogen Bonds in Supramolecular Systems Using 1H–15N Heteronuclear Multiple Quantum Coherence Spectroscopy Michael A. Jinks, Mark Howard, Federica Rizzi, Stephen M. Goldup, Andrew D. Burnett, and Andrew J. Wilson,* J. Am. Chem. Soc. 2023, 144, 23127. (ChemRXiv Preprint). A catenane whose stereochemistry is Euclidean but equivalent to that of reported topologically chiral catenanes Noel Pairault, Federica Rizzi, David Lozano, Graham J. Tizzard, Ellen M. G. Jamieson, Stephen M. Goldup,* Nat. Chem. 2023, accepted (ChemRXiv Preprint). A Chiral Macrocycle for the Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes and Catenanes Shu Zhang, Arnau Rodríguez-Rubio, Abed Saady, Graham J. Tizzard, Stephen M. Goldup,* Chem 2023, accepted (ChemRXiv Preprint). A Co-conformationally “Topologically” Chiral Catenane Arnau Rodríguez-Rubio, Andrea Savoini, Florian Modicom, Patrick Butler, Stephen M. Goldup,* J. Am. Chem. Soc. 2022, 144, 11927. (ChemRXiv Preprint). Mechanically axially chiral catenanes and noncanonical chiral rotaxanes John R. J. Maynard, Pater Gallagher, David Lozano, Patrick Butler, Stephen M. Goldup,* Nat. Chem. 2022, 14, 1038 (ChemRXiv Preprint). Anion-pi Catalysis Enabled by the Mechanical Bond John R. J. Maynard, Bartomeu Galmés, Athanasios D. Stergiou, Mark D. Symes, Antonio Frontera,* Stephen M. Goldup,* Angew. Chem. Int. Ed. 2022, 61, e202115961 (ChemRXiv Preprint). Controlling catalyst activity, chemo- and stereo-selectivity with the mechanical bond Andrew W. Heard, Jorge Meijide Suárez, and Stephen M. Goldup,* Nat. Rev. Chem. 2022, 6, 182. A Chiral Interlocking Auxiliary Strategy for the Synthesis of Mechanically Planar Chiral Rotaxanes Alberto de Juan, David Lozano, Andrew Heard, Michael Jinks, Jorge Meijide Suarez, Graham J. Tizzard, Stephen Goldup,* Nature Chem. 2022, 14, 179 (ChemRxiv preprint). 65. Spin-Labelled Mechanically Interlocked Molecules as Models for the Interpretation of Biradical EPR Spectra Lorenzo Gualandi, Paola Franchi, Elisabetta Mezzina, Stephen M. Goldup,* Marco Lucarini,* Chem. Sci. 2021, 12, 8385 (ChemRxiv preprint). Rotaxane CoII Complexes as Field-Induced Single-Ion Magnets Cirulli, Enrico Salvadori, Zhi-Hui Zhang, Michael Dommett, Floriana Tuna, Heiko Bamberger, James Lewis, Amanpreet Kaur, Graham Tizzard, Joris van Slageren, Rachel Crespo Otero,* Stephen M. Goldup,* Maxie Roessler* Angew. Chem. Int. Ed. 2021, 60, 16051. (ChemRxiv preprint). Damming a Molecular Energy Reservoir: Ion-regulated Electronic Energy Shuttling in a [2]Rotaxane Arkady Kurpryakov, James Lewis, Vicente Martí-Centelles, Stephen Goldup,* Jean-Luc Pozzo, Gediminas Jonusauskas, Nathan McClenaghan* Chem. Sci. 2021, 12, 9196 (ChemRxiv preprint). Using the Mechanical Bond to Tune the Performance of a Thermally Activated Delayed Fluorescence Emitter Pachaiyappan Rajamalli, Federica Rizzi, Wenbo Li, Michael Jinks, Abhishek Kumar Gupta, Beth Laidlaw, Ifor Samuel,* Thomas Penfold,* Steve Goldup,* Eli Zysman-Colman* Angew. Chem. Int. Ed. 2021, 60, 12066. (ChemRxiv preprint). Strategies for the Synthesis of Enantiopure Mechanically Chiral Molecules John R. J. Maynard, Stephen M. Goldup,* Chem 2020, 6, 1914. Vibrational Circular Dichroism Spectroscopy for Probing the Expression of Chirality in Mechanically Planar Chiral Rotaxanes Mark Antonius Johannes Koenis, Chima Chibueze, Michael Jinks, Valentin Nicu, Lucas Visscher, Stephen M. Goldup,* Wybren Jan Buma,* Chem. Sci. 2020, 11, 8469. Rotaxanation as a sequestering template to preclude incidental metal insertion in complex oligochromophores Huynh Thien Ngo,* James E. M. Lewis, Daniel T. Payne, Francis D’Souza, Jonathan P. Hill, Katsuhiko Ariga, Genki Yoshikawa, Stephen M. Goldup, Chem. Commun. 2020, 56, 7447. AT-CuAAC Synthesis of Mechanically Interlocked Oligonucleotides Amanda Acevedo-Jake, Andrew T. Ball, Marzia Galli, Mikiembo Kukwikila, Mathieu Denis, Daniel G. Singleton, Ali Tavassoli,* Stephen M. Goldup,* J. Am. Chem. Soc. 2020, 142, 5985 (ChemRrxiv preprint). Simplicity in the Design, Operation and Applications of Mechanically Interlocked Molecular Machines Andrew W. Heard, Stephen M. Goldup,* ACS Cent. Sci. 2020, 6, 117. Rotaxane Pt(II)-complexes: mechanical bonding for chemically robust luminophores and stimuli responsive behaviour Zhihui Zhang, Graham J. Tizzard, J .A. Gareth Williams,* Stephen M. Goldup,* Chem. Sci. 2020, 11, 1839. A Mechanically Planar Chiral Rotaxane Ligand for Enantioselective Catalysis Andrew W. Heard, Stephen M. Goldup,* Chem 2020, 6, 1914 (ChemRxiv preprint) Chirality makes a move Ellen M. G. Jamieson, Stephen M. Goldup,* Nature Chem. (N&V) 2019, 765. An Auxiliary Approach for the Stereoselective Synthesis of Topologically Chiral Catenanes Mathieu Denis, James E. M. Lewis, Florian Modicom, Stephen M. Goldup,* Chem. 2019, 5, 1357. Chemical Consequences of the Mechanical Bond: A Tandem Active Template-Rearrangement Reaction Florian Modicom, Ellen M. G. Jamieson, Elise Rochette, and Stephen M. Goldup,* Angew. Chem. Int. Ed. 2019, 58, 3875. Rotaxane-Based Transition Metal Complexes: Effect of the Mechanical Bond on Structure and Electronic Properties Martina Cirulli, Amanpreet Kaur, James E. M. Lewis, Zhihui Zhang, Jonathan A. Kitchen, Stephen M. Goldup,* and Maxie M. Roessler,* J. Am. Chem. Soc. 2018, 141, 879. Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes Michael A. Jinks, Alberto de Juan, Mathieu Denis, Catherine J. Fletcher, Marzia Galli, Ellen M. G. Jamieson, Florian Modicom, Zhihui Zhang, and Stephen M. Goldup,* Angew. Chem. Int. Ed. 2018, 57, 14806. Molecular Machines Swap Rings (Invited N&V) Stephen M. Goldup,* Nature 2018, 557, 39. Chirality in Rotaxanes and Catenanes Ellen M. G. Jamieson, Florian Modicom, Stephen M. Goldup,* Chem. Soc. Rev. 2018, 47, 5266. A [3]Rotaxane Host Selects Between Stereoisomers (Invited highlight)Mathieu Denis, Stephen M. Goldup,* Angew. Chem. Int. Ed 2018, 57, 4462. Efficient Multi-Component Active Template Synthesis of Catenanes James E. M. Lewis, Florian Modicom, Stephen M. Goldup,* J. Am. Chem. Soc. 2018, 140, 4787. Chelating Rotaxane Ligands as Fluorescent Metal Ion Sensors Mathieu Denis, Jessica Pancholi, Kajally Jobe, Michael Watkinson,* Stephen M. Goldup,* Angew. Chem. Int. Ed. 2018, 57, 5310. A Fluorescent Ditopic Rotaxane Ion-Pair Host Mathieu Denis, Lei Qin, Peter Turner, Katrina A. Jolliffe,* Stephen M. Goldup,* Angew. Chem. Int. Ed. 2018, 57, 5315. Synthesis and Characterisation of a Paramagnetic [2]Rotaxane Based on a Crown Ether-Like Wheel Incorporating a Nitroxide Motif Valentina Bleve, Paola Franchi, Evangelia Konstanteli, Lorenzo Gualandi, Stephen M. Goldup, Elisabetta Mezzina,* Marco Lucarini,* Chem. Eur. J. 2018, 24, 1198.

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