Presentations

K. Ramsay^1*, J. Levy¹, P. Gobbo², K. Elvira¹

¹University of Victoria, ²Bristol University

The ability to build biological tissues from their most fundamental chemical constituents has long been a subject of interest in the evolutionary, medical and materials science communities. When these chemical constituents become a primordial form of life they are referred to as protocells. A step up from protocells are prototissues; a combination of protocells that perform a collaborative function. Here we have outlined a cutting-edge approach for the bottom-up creation of prototissues using microfluidic technology. Our research group has developed a microfluidic platform for the creation of multicompartmental droplets, which is particularly advantageous for the biochemical engineering of artificial cells and tissues as it allows us to achieve a level of precision, consistency and accuracy that cannot be accessed using conventional methods such as centrifugation or manual shaking. Some of these inner droplets are tagged with an azide-conjugated bovine serum albumin nanoconjugate and the others with a bicyclononyne nanoconjugate. The unique geometric configurations and thermoresponsivities of these interlinked prototissues were further analyzed. Overall, our microfluidic methodology opens up a unique route to the bottom-up fabrication of artificial tissue-like materials capable of collective behaviours and addresses an important gap in the fundamentals of the prototissue chemistry.

D. Yeung

University of Manitoba

In the ever expanding field of proteomics, 2D-LC MS/MS has been a staple for digging deeper in the analysis of complex proteomes. Current standards include pairing: Strong-Anion Exchange (SAX) with Reverse Phase (RP), pH 10 RP with pH 4.5 RP, Hydrophilic Interaction Liquid Chromatography (HILIC) with RP, but how do we know which has the best identifications? From our decades of experience in modeling predictive algorithms for chromatographic columns with SSRCalc, we set out to establish a standard for which proteomics practioners can refer to for their sample preparation in 2D-LC MS/MS. Assessing 16 different chromatographic columns and their pairing against RP, we quantitative measure the orthogonality between different columns to understand their differences in separation mechanisms. Does higher orthogonality lead to larger identification? 

F. L. Buguis^*, R. R. Maar, V. N. Staroverov, J. B. Gilroy

The University of Western Ontario

Chromophores that exhibit optical properties, such as absorbance and photoluminescence, in the far-red and near-infrared (NIR) spectral regions have garnered significant attention. These dyes are sought after due to their utility in material science and bioimaging applications, leading to the continuous search for new architectures. Typical challenges that need to be overcome in this research space are long synthetic routes and expensive starting materials. In our most recent efforts, the addition of tertiary amine substituents into the BF₂-formazanate architecture yielded chromophores with NIR optical properties similar to dyes with more complex structures. Cyclic voltammetry experiments revealed multiple reversible redox waves linked to the interplay between the tertiary amine and formazanate moieties. Density-functional calculations revealed  the electronic transitions to be π→π^* type between strongly delocalized molecular orbitals with an exception of one dye exhibiting charge-transfer type transitions. The insights gained in this work serve as a platform for next-generation BF₂-formazanate dyes and demonstrate the feasibility of relatively simple π-conjugated systems for NIR applications.

J. S. Dhindsa^*, R. R. Maar, S. M. Barbon, J. B. Gilroy

The University of Western Ontario

Organic π-conjugated molecular and polymeric materials exhibit sought after optical and electronic properties due to the delocalization of π-electrons within their frameworks and are often semiconducting. This leads to their use in a variety of organic electronics such as light emitting diodes, lasers, photovoltaic devices, memory devices, etc. Incorporating platinum(II) into the main chain of these systems is known to afford a variety of advantageous properties such as photoluminescence, redox activity, and optoelectronic properties. The general structure for platinum polyynes is a linear backbone comprised of the platinum(II) centre, supported by neutral phosphine ligands, and a spacer group. Herein, we introduce a readily accessible conjugated polymer and several molecular compounds that couple electron-poor boron difluoride formazanate spacers and electron-rich platinum(II)-acetylide subunits as promising candidates for use in organic electronics. We have also demonstrated advantageous thin film forming properties and stepwise, controlled chemical reduction of the polymer.

L. Porto^*, R. T. Baker

University of Ottawa

Fluorine’s high electronegativity and small size bestows unique and advantageous physical and chemical effects on its compounds. The inclusion of fluorine and fluoroalkyl groups into organic molecules enhances the bioactivity and modulates pharmacokinetics, thus representing an important class of targets for medicinal chemistry. In 2018, Baker et al. synthesized LnCu-CF(CF₃)₂ (Cu-HFIP) reagents by insertion of hexafluoropropene, F₂C=CF(CF₃), into (PPh₃)₃Cu-F. Using phenanthroline as ancillary ligand, they demonstrated efficient transfer of the HFIP group to aroyl chlorides. In this work, we describe the generation of a new RF group [-CF(OCF₃) (CF₂H)] from reaction of F₂C=CF(OCF₃) with [(PPh₃)CuH]₆ (Stryker's reagent) and PPh₃. We isolated three different complexes with one N-heterocyclic carbene (NHC), two PPh₃ and three P(OEt)₃ ligands and only that with NHC was able to transfer the RF to aroyl chlorides. Attempts using bipy or DMSO as a ligand (1 equivalent) yielded an expansion of the organic electrophile substrate scope (to aryl iodides, for example). We are currently working with a computational chemistry collaborator to better understand the ligand dependence on transfer efficiency of this RF group.

Y. Albkuri^1*, R. Baker¹, C. Bucher²

¹University of Ottawa, ²Laboratoire de Chemie,Lyon-France

In contrast to its Ni SN thiolate-imine analog, thermolysis of our Ni SNS bis(thiolate) complex (1) does not cleanly afford the Ni(N₂S₂) isomer (2). However, electrochemical studies show that reduction of 1 gives 2^- quantitatively.The latter is then readily oxidized using ferrocenium salts to give a high yield of 2. The CV of isolated 2 also shows a second reversible reduction wave, yielding the diamagnetic zerovalent Ni complex 2^2-. In this presentation, we compare the reactivity of 1 with that of the three redox states of 2.