Dr Jack Chen

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Senior Lecturer - Chemistry

Email: jack.chen@aut.ac.nz

ORCID: ORCID logo  https://orcid.org/0000-0002-4662-4076

Links to relevant web pages:

www.jchenresearch.wordpress.com/

Qualifications:

BSc(Hons), PhD (University of Auckland)

Biography:

Our group is interested in the way molecules and nanoparticles self-organise into functional architectures. We are currently introducing responsive elements into systems that allow them to respond to light, transmit signals and demonstrate adaptive properties. Such systems offer exciting possibilities for the development of molecular machines, smart materials and molecular electronics.

I conducted my PhD at the University of Auckland with Prof. Margaret Brimble, working on the synthesis of spirastrellolide B - a potent protein phosphatase inhibitor with potential anti-cancer properties. I then took up a Postdoctoral Fellow appointment in the same group for 18 months, and was involved in a range of projects including the total synthesis of bioactive molecules from traditional Chinese medicines and a medicinal chemistry project to discover novel telomerase inhibitors. In 2011 I moved to Bristol, UK, for 3 years where I worked with Prof. Varinder Aggarwal developing synthetic methodology involving a novel form of activated allylboron reagents. In 2014 I took up a Postdoctoral Fellowship with Prof. Leonard Prins in Padova, Italy, where I studied the use of gold nanoparticle-based supramolecular systems for chiral catalysis. In July 2016 I joined the staff at the School of Science at AUT.

Teaching Areas:

Organic Chemistry, Molecular Design, General Chemistry

Research Areas:

*    Self-assembly and emergent properties
*    Dynamic functional nanosystems
*    Reaction kinetics and mechanism
*    Green catalysis and sustainable chemistry

Current Research Projects:

Dynamic self-assembled systems responsive to external stimuli

Our group is interested in the way molecules and nanoparticles self-organise into functional architectures. We are currently utilising self-assembly to construct dynamic structures that possess emergent properties. This is possible by utilising cooperative effects - where multiple functional groups work together to exhibit properties that are not observed in the original building blocks. Such dynamic systems allow the introduction of stimuli-responsive moieties that allow these systems to respond to chemical fuels, light and other external stimuli. Such responsive systems offer exciting possibilities for the development of molecular machines, smart materials and molecular electronics.

Sustainable chemistry in water catalysed by multi-functional gold nanoparticles

In the current battle against climate change, chemists have an even greater responsibility to conduct chemistry with low environmental impact. This means following green chemistry principles such as utilising catalysis and minimising waste. The proposed project aims to immobilise catalysts onto gold nanoparticles which are water soluble, creating catalysts which are effective in water, and which are easily recyclable. How different immobilisation methods affect the kinetics and mechanisms of different reactions will be studied. Reactions of interest include ester formation driven by phase separation, the kinetic resolution of terminal epoxides and aldol reactions catalysed by proline-based organocatalysts. The immobilisation of multiple catalysts will also enable the development of cascade reaction methodology, another important goal in green and sustainable chemistry.

Project1_Original

Publications:

Chloe Z.-J. Ren, Pablo Solís Muñana, Julien Dupont, Silvia S. Zhou, Jack L.-Y. Chen*. Reversible Formation of a Light-responsive Catalyst by Utilizing Intermolecular Cooperative Effects. Angew. Chem. Int. Ed. 2019Accepted article, DOI: 10.1002/anie.201907078. link

Pablo Solís Muñana†, Giulio Ragazzon†, Julien Dupont, Chloe Z.‐J. Ren, Leonard J. Prins*, Jack L.‐Y. Chen*. Substrate‐Induced Self‐Assembly of Cooperative Catalysts. Angew. Chem. Int. Ed. 2018, 57, 16469-16474 (†denotes equal contribution) link

C. García-Ruiz, Jack L.-Y. Chen, C. Sandford, K. Feeney, P. Lorenzo, G. Berionni, H. Mayr, and V. K. Aggarwal. Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles. J. Am. Chem. Soc. 2017, 139, 15324. link

Jack L.-Y. Chen, S. Maiti, I. Fortunati, C. Ferrante, L. J. Prins. Temporal Control over Transient Chemical Systems using Structurally Diverse Chemical Fuels. Chem. Eur. J. 201723, 11549 (Selected as a Hot Paper by the Editors ). link

F. della Sala, S. Neri, S. Maiti, Jack L.-Y. Chen, L. J. Prins. Transient Self-Assembly of Molecular Nanostructures Driven by Chemical Fuels. Curr. Opin. Biotechnol. 201746, 27-33. link

F. della Sala, Jack L.-Y. Chen, S. Ranallo, D. Badocco, P. Pastore, F. Ricci, L. J. Prins. Reversible Electrochemical Modulation of a Catalytic Nanosystem. Angew. Chem. Int. Ed. 201655, 10737-10740. link

C. Pezzato, Jack L.-Y. Chen, P. Galzerano, M. Salvi, L. J. Prins. Catalytic signal amplification for the discrimination of ATP and ADP using functionalised gold nanoparticles. Org. Biomol. Chem. 201614, 6811. link

Jack L.-Y. Chen, C. Pezzato, P. Scrimin, L. J. Prins, Chiral Nanozymes – Gold Nanoparticle-based Transphosphorylation Catalysts Capable of Enantiomeric Discrimination. Chem. Eur. J. 201622, 7028-7032 (Highlighted with frontispiece cover). link

A. Millan, J. R. Smith, Jack L.-Y. Chen, V. K. Aggarwal, Tandem Allylboration-Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (-)-Clavosolide A. Angew. Chem. Int. Ed. 2016, 55, 2498-2502 (selected as a Hot Paper by the Editors). link

C. Pezzato, S. Maiti, Jack L.-Y. Chen, A. Cazzolaro, C. Gobbo, L. J. Prins, Monolayer protected gold nanoparticles with metal-ion binding sites: functional systems for chemosensing applications. Chem Commun. 2015, 51, 9922-9931. link

Jack L.-Y. Chen, V. K. Aggarwal. Highly Diastereoselective and Enantiospecific Allylation of Ketones and Imines using Borinic Esters: Contiguous Quaternary Stereogenic Centers. Angew. Chem. Int. Ed. 2014, 53, 10992-10996 (designated VIP paper). link

H. M. Geng, L. A. Stubbing, Jack L.-Y. Chen, D. P. Furkert, M. A. Brimble. Synthesis of the Revised Structure of Acortatarin A. Eur. J. Org. Chem. 2014, 6227-6241. link

L. Chausset-Boissarie, K.Ghozati, E. LaBine, Jack L.-Y. Chen, V. K. Aggarwal, C. M. Crudden. Enantiospecific, Regioselective Cross-Coupling Reactions of Secondary Allylic Boronic Esters. Chem. Eur. J. 2013, 19, 17698-17701. link

Jack L.-Y. Chen, H. K. Scott, M. J. Hesse, C. L. Willis, V. K. Aggarwal. Highly Diastereo- and Enantioselective Allylboration of Aldehydes using α‑Substituted Allyl/Crotyl Pinacol Boronic Esters via in Situ Generated Borinic Esters. J. Am. Chem. Soc. 2013, 135, 5316-5319. link

T.-Y. Yuen, Y.-P. Ng, F. C. F. Ip, Jack L.-Y. Chen, D. J. Atkinson, J. Sperry, N. Y. Ip, M. A. Brimble. Telomerase Inhibition Studies of Novel Spiroketal-Containing Rubromycin Derivatives. Aust. J. Chem. 2013, 66, 530-533. link

H. M. Geng, Jack L.-Y. Chen, D. P. Furkert, S. Jiang, M. A. Brimble. A Convergent Synthesis of the 2-Formylpyrrole Spiroketal Natural Product Acortatarin A. Synlett 2012, 23, 855-858. link

D. F. Chorley, Jack L.-Y. Chen, D. P. Furkert, J. Sperry, M. A. Brimble. Total Synthesis of Danshenspiroketallactone. Synlett 2012, 23, 128. link

Jack. L.-Y. Chen, J. Sperry, N. Y. Ip. M. A. Brimble. Natural products targeting telomere maintenance. Med. Chem. Commun. 2011, 2, 229-245. link

Jack L.-Y. Chen, M. A. Brimble. Synthesis of the Bis-Spiroacetal Core of the Antimitotic Agent Spirastrellolide B. J. Org. Chem. 2011, 76, 9417-9428. link

Jack L.-Y. Chen, M. A. Brimble. Synthesis of the bis-spiroacetal C25-C40 moiety of the antimitotic agent spirastrellolide B using a bis-dithiane deprotection/spiroacetalisation sequence. Chem. Commun. 2010, 46, 3967-3969. link