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Instruments / Technical Area	Publication Details	Published
I19-Small Molecule Single Crystal Diffraction	Lithium half-salen complexes: Synthesis, structural characterization and studies as catalysts for rac-lactide ring-opening polymerization Yali Zhou , Gary S. Nichol , Jennifer A. Garden European Journal Of Organic Chemistry 2021, 5557 - 5568 DOI: 10.1002/ejoc.202100981 Diamond Proposal Number(s): [22240] Open Access Show Abstract ▼ Abstract: Seven lithium complexes supported by sterically and electronically diverse phenoxyimine ligands were synthesized and characterized by X-ray diffraction, NMR spectroscopy and elemental microanalysis. These complexes show high activity (kobs ≤7.43×10−2 s−1) for rac-lactide ring-opening polymerization (ROP) in the presence of co-initiator benzyl alcohol (BnOH), with the exception of Li4 which features an unusual polymeric ladder structure. Overall, the catalyst activity correlates to the aggregation state; the catalysts with low aggregation states display increased propagation rates attributed to improved metal accessibility and kinetic mobility. The nature of the ligand substituents and solvent influence the catalyst aggregation in both the solid- and solution-state. While the lithium complexes can initiate rac-lactide ROP without BnOH, the addition of this co-initiator significantly increases the polymerization rate by switching the mechanism from a coordination-insertion to an activated monomer pathway, changing the resultant poly(lactic acid) architecture from cyclic to linear.	Oct 2021
I19-Small Molecule Single Crystal Diffraction	Synchronized “click” and templated synthesis of a fluorescent pyrene crown ether Yvonne Choo , Paul Waddell , Andrew Benniston European Journal Of Organic Chemistry DOI: 10.1002/ejoc.201900125 Show Abstract ▼ Abstract: The reaction of 6,8‐bisethynylpyrene‐2‐carboxylic acid methyl ester with 1‐azido‐2‐(2‐(2‐azidoethoxy)ethoxy)ethoxy)ethane using standard “click” chemistry produced a 1+1 crown ether (CPYR). The copper ions used both catalyse the reaction and provide a template for ensuring smooth cyclisation. The X‐ray crystal structure of the compound reveals the two triazole groups are non‐coplanar with the pyrene moiety. The triazole groups are more co‐planar with the pyrene subunit in the first‐excited singlet state as revealed by a DFT calculated molecular structure (B3LYP, 6‐311G). Partially structured emission observed in acetonitrile is consistent with the calculation result. In acetonitrile solution the macrocycle CPYR interacts with a Na+ ion to form a complex in which the ion binds with the crown and the pyrene residue.	Feb 2019
B23-Circular Dichroism	Self-assembled porphyrazine-nucleoside on DNA templates: highly fluorescent chromophore arrays and sizing forensic tandem repeat sequences Mariia V. Ishutkina , Alice R. Berry , Rohanah Hussain , Olga G. Khelevina , Giuliano Siligardi , Eugen Stulz European Journal Of Organic Chemistry DOI: 10.1002/ejoc.201800683 Diamond Proposal Number(s): [13158] Open Access Show Abstract ▼ Abstract: The formation of chromophore arrays using a DNA templating approach leads to the creation of supramolecular assemblies, where the optical properties of the overall system can be fine‐tuned to a large extent. In particular porphyrin derivatives have shown to be versatile building blocks; mostly covalent chemistry was used for embedding the units into DNA strands. Self‐assembly of porphyrin modified nucleosides, on the other hand, has not been investigated as a simplified approach. We report on the synthesis of a magnesium(II) tetraaza porphine (MgTAP) coupled to deoxy‐uridine, and array formation on DNA templates which contain well‐defined oligo(dA) segments showing strong fluorescence enhancement which is significantly larger than with a Zn‐porphyrin. The use of the deep‐eutectic solvent glycholine is essential for successful assembly formation. The system allows for sizing of short tandem repeat markers with multiple adenosines, thus the concept could be adaptable to in vitro forensic DNA profiling with a suitable set of different chromophores on all nucleosides.	May 2018
I19-Small Molecule Single Crystal Diffraction	Highly diastereo- and enantioselective synthesis of α-spiro-δ-lactams by an organocascade reaction Kaiheng Zhang , Marta Meazza , Vojtěch Dočekal , Mark Light , Jan Veselý , Ramon Rios European Journal Of Organic Chemistry 2017, 1749 - 1756 DOI: 10.1002/ejoc.201700193 Diamond Proposal Number(s): [8521] Show Abstract ▼ Abstract: An asymmetric synthesis of α-spiro-δ-lactams by an organocascade reaction of easily accessible starting materials has been accomplished. The catalytic sequence begins with enantioselective Michael addition of a β-ketoamide to an α,β-unsaturated aldehyde, catalyzed by a secondary amine catalyst, and is followed by hemiaminal annulation. Optically enantiopure compounds with three stereogenic centres are obtained in good yields and excellent selectivities (up to >20:1 dr and up to >99 % ee).	Apr 2017
I19-Small Molecule Single Crystal Diffraction	Highly enantioselective synthesis of alkyl-pyridines derivatives through a Michael-Michael-aldol cascade reaction Marta Meazza , Michael Potter , Mateusz Pitak , Simon Coles , Andrea Mazzanti , Ramon Rios Torres European Journal Of Organic Chemistry DOI: 10.1002/ejoc.201601491 Diamond Proposal Number(s): [8521] Show Abstract ▼ Abstract: A new methodology for the synthesis of pyridine derivatives based on a triple cascade reaction catalyzed by chiral secondary amines. The resulting cyclohexenes (3 C-C bond were formed) were obtained in good yields, good diastereoselectivities and excellent enantioselectivity	Nov 2016

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