The synthesis, symmetry and applications of interlocked molecules

 

The synthesis, symmetry and applications of interlocked molecules

Date: 5^thDecember, 2024 (Thursday)

Time: 5 - 6 pm (HKT)

Venue: Lecture Theatre P3, Chong Yuet Ming Physics Building

 

Prof. Stephen Goldup

University of Birmingham

 

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 postdoctoral 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 and in 2019 was awarded a Royal Society Wolfson Research Fellowship. Recently, the group moved from Southampton to the University of Birmingham where Steve is Chair of Supramolecular Chemistry. Research in the Goldup Group focusses on the synthesis of novel mechanically interlocked molecules and their application as sensors, catalysts and materials. Steve has received awards from the Royal Society of Chemistry and Blavatnik Family Foundation, as well as fellowships from the Royal Society and Leverhulme Trust.

 

Threading one molecule through another to generate what is now called “the mechanical bond” was first discussed in 1912¹ but it took a further 50 years for the first synthetic example to be produced in extremely low yield.² From there, it took another 22 years for the first scalable synthesis to be reported³ and it is only recently that the synthesis of such molecules has become relatively trivial, allowing their potential applications to be studied and developed. Of these possible applications, the most famous is the use of catenanes and rotaxanes as components of molecular machines.⁴ However, the mechanical bond also augments the chemical properties of the threaded molecules.⁵

 

In the Goldup Group we develop simple methods and concepts to access challenging mechanically interlocked structures so that we can demonstrate the potential chemical applications of the mechanical bond in catalysis,⁶ sensing,⁷ coordination chemistry,⁸ chemical biology,⁹ materials science and indeed anywhere that molecules are used! We have a particular interest in how the mechanical bond leads to unusual forms of stereochemistry.¹⁰ My lecture will give an overview of our activities.

 

[1] H. L. Frisch, E. Wasserman, J. Am. Chem. Soc. 1961, 83, 3789-3795.

[2] E. Wasserman, J. Am. Chem. Soc. 1960, 82, 4433-4434.

[3] C. O. Dietrich-Buchecker, J. P. Sauvage, J. P. Kintzinger, in Tetrahedron Letters, Vol. 24, 1983, pp. 5095-5098

[4] (a) J. P. Sauvage, Angew. Chem. Int. Ed. 2017, 56, 11080-11093; (b) J. F. Stoddart, Angew. Chem. Int. Ed. 2017, 56, 11094-11125; (c) B. L. Feringa, Angew. Chem. Int. Ed. 2017, 56, 11060-11078.

[5] E. A. Neal, S. M. Goldup, Chem. Commun. 2014, 50, 5128-5142

[6] (a) M. Galli, J. E. Lewis, S. M. Goldup, Angew. Chem. Int. Ed. 2015, 54, 13545-13549 (b) A. W. Heard, S. M. Goldup, Chem 2020, 6, 994-1006 (c) R. W. Heard, J. M. Suarez, S. M. Goldup, Nat. Rev. Chem. 2022, 6, 182-196 (d) J. R. J. Maynard, B. Galmes, A. D. Stergiou, M. D. Symes, A. Frontera, S. M. Goldup, Angew. Chem. Int. Ed. 2022, 61, e202115961

[7] (a) M. Denis, J. Pancholi, K. Jobe, M. Watkinson, S. M. Goldup, Angew. Chem. Int. Ed. 2018, 57, 5310-5314; (b) M. Denis, L. Qin, P. Turner, K. A. Jolliffe, S. M. Goldup, Angew. Chem. Int. Ed. 2018, 57, 5315-5319

[8] (a) M. Cirulli, A. Kaur, J. E. M. Lewis, Z. Zhang, J. A. Kitchen, S. M. Goldup, M. M. Roessler, J. Am. Chem. Soc. 2019, 141, 879-889; (b) Z. Zhang, G. J. Tizzard, J. A. G. Williams, S. M. Goldup, Chem. Sc. 2020, 11, 1839-1847; (c) M. Cirulli, E. Salvadori, Z. H. Zhang, M. Dommett, F. Tuna, H. Bamberger, J. E. M. Lewis, A. Kaur, G. J. Tizzard, J. van Slageren, R. Crespo-Otero, S. M. Goldup, M. M. Roessler, Angew. Chem. Int. Ed. 2021, 60, 16051-16058.

[9] (a) A. Acevedo-Jake, A. T. Ball, M. Galli, M. Kukwikila, M. Denis, D. G. Singleton, A. Tavassoli, S. M. Goldup, J. Am. Chem. Soc. 2020, 142, 5985-5990; (b) A. Saady, G. Malcolm, M. Fitzpatrick, N. Pairault, G. Tizzard, S. Mohammed, A. Tavassoli, S. M. Goldup, Angew. Chem. Int. Ed. 2024, e202400344.

[10] (a) R. J. Bordoli, S. M. Goldup, J. Am. Chem. Soc. 2014, 136, 4817-4820; (b) M. A. Jinks, A. de Juan, M. Denis, C. J. Fletcher, M. Galli, E. M. G. Jamieson, F. Modicom, Z. Zhang, S. M. Goldup, Angew. Chem. Int. Ed. 2018, 57, 14806-14810; (c) M. Denis, J. E. M. Lewis, F. Modicom, S. M. Goldup, Chem 2019, 5, 1512-1520; (d) A. de Juan, D. Lozano, A. W. Heard, M. A. Jinks, J. M. Suarez, G. J. Tizzard, S. M. Goldup, Nat. Chem. 2022, 14, 179-187; (e) J. R. J. Maynard, P. Gallagher, D. Lozano, P. Butler, S. M. Goldup, Nat. Chem. 2022, 14, 1038-1044; (f) N. Pairault, F. Rizzi, D. Lozano, E. M. G. Jamieson, G. J. Tizzard, S. M. Goldup, Nat. Chem. 2023, 15, 781-786; (g) S. Zhang, A. Rodríguez-Rubio, A. Saady, G. J. Tizzard, S. M. Goldup, Chem 2023, 9, 1195-1207; (h) P. Gallagher, A. Savoini, A. Saady, J. Maynard, P. Butler, G. Tizzard, S. Goldup, J. Am. Chem. Soc. 2024, accepted; (i) A. Savoini, P. Gallagher, A. Saady, S. Goldup, J. Am. Chem. Soc. 2023, accepted.