Orlando De Azevedo

The main project, within Prof. Olalla Vázquez Research Group, involved the synthesis, characterization and spectroscopic evaluation of structurally diverse rhodamines for application as triplet photosensitizers. I was involved in a second project regarding the multi-step synthesis and characterization of a photoswitchable Peptide Nucleic Acid (PNA) monomer. Other side projects included the preparation of a photoswitchable peptide for a Collaborator and the multi-step synthesis of Si-DMA to be used within the Research Group. Projects were target-focused, involving milligram to gram scale multi-step organic synthesis intercalated with characterization techniques including Multidimensional Nuclear Magnetic Resonance (NMR), High-Resolution Mass Spectrometry (HRMS) and UV-Vis Spectroscopy. Routine purification was performed by Column Chromatography, Preparative Thin-Layer Chromatography and Büchi Normal- and Reverse-Phase Chromatography systems. Schlenk line techniques were commonly used for air-sensitive reactions.

Other job responsibilities included:

• Project planning based on the overall project scope, budget, timelines, available resources and risks.
• Keeping up to date records of laboratory progress, presenting biweekly presentations in Group Seminars, preparing quarterly reports and communicating regularly the project progress to the Project Manager either through person-to-person meetings or through Slack.
• Management of a project run with one MSc undergraduate student. This included the design of a project plan. Variables considered included project scope, objectives/goals, existing budget, scheduling, available resources and, also importantly, the student’s motivation and availability. Monitor and supervise the project in a daily basis. Identification of gaps and potential problems in the on-going project to optimize and increase the probability of its success. Assistance on the reporting of the project.
• Laboratory management: a) Purchasing chemicals, glassware and other laboratory equipment for on-going projects; b) Assisting on routine tasks in the laboratory.
• Lecturer in OC-MPR - Masterpraktikum Organische Chemie class.

Project entitled "Multifunctional wound healing peptide hydrogels’ was funded through the "GO-Bio-initial" grant sponsored by the German Federal Ministry of Education and Research (BMBF) under supervision of Dr. Chaitanya Thota at Freie Universität Berlin. I was hired to perform the synthesis and characterization of structurally diverse peptides for the preparation of hydrogels for medicinal applications. Project was mainly target-focused, involving milligram to gram scale multi-step organic synthesis intercalated with characterization techniques including Multidimensional Nuclear Magnetic Resonance (NMR), High-Resolution Mass Spectrometry (HRMS) and Elemental Analysis (EA). Solid-Phase Peptide Synthesis (SPPS) was performed occasionally. Bench-scale hydrogelation was accomplished and preliminary evaluation of the physical properties of the hydrogels was performed.

Project funded by Hoya Corporation (Japan) that involved the multi-step synthesis and characterization of photochromic organic molecules with potential mesogenic properties (Patents: EP4067353A1,EP4067362A1, US20220315831A1, US20220325171A1). Projects were mainly target-focused, involving small (50 – 100 mg) and large scale (100 – 200 g) multi-step organic synthesis intercalated with characterization techniques including Multidimensional Nuclear Magnetic Resonance Spectroscopy (NMR), High-Resolution Mass Spectrometry (HRMS), X-Ray Crystallography, Infrared Spectroscopy (FT-IR) and Elemental Analysis (EA). Photophysical characterization of final targets was achieved using a bespoke UV-Vis Spectrophotometer irradiation system, Fluorescence Spectroscopy and Time-Correlated Single-Photon Counting. Routine purification was performed by Column Chromatography and Preparative Thin-Layer Chromatography. Schlenk line techniques were commonly used for air-sensitive reactions.

Job responsibilities included:

• Development of a comprehensive research plan to organise and conduct multiple projects while fulfilling tight deadlines.
• Multi-step synthesis and characterization of photochromic heterocycles.
• Keeping up to date records of laboratory progress and preparing quarterly reports.
• Set-up regular meetings to share and review the progress of the project with the key Stakeholders.
• Laboratory management: a) Laboratory Health & Safety officer; b) Responsible for the regular update of laboratory catalogues of chemical reagents and solvents; c) Purchasing chemicals, glassware and other laboratory equipment for personal and undergraduate projects; d) Assisting on routine equipment repair/maintenance.
• Direct supervision of up to three undergraduate research projects.
• Providing training and instruction to MSc and PhD students regarding theoretical concepts, laboratory skills and techniques.
• · Writing scientific papers to publish in peer-reviewed scientific journals with high impact factors.
• · Presenting research output at national and international conferences/meetings.
• · Keeping abreast of the scientific literature (particularly synthetic methodology, photochromism and materials chemistry).
• · Lecturer in charge (demonstrating and marking) of Year 1 Practical Organic Chemistry classes (2021).

In this short commercially focused project, several novel metalloporphyrin salts were prepared for biological / agrochemical testing. Methodological breakthroughs were accomplished, which offered savings in reactants, reaction time and processing time. Additionally, various methods of ion exchange of the counterions of the metal porphyrins salts were developed.

A novel N-linked porphyrin-flavone conjugate, connected through the para position of the mesophenyl group, was synthesized from a Buchwald-Hartwig amination reaction between 4’-bromoflavone and 5-(4-aminophenyl)-10,15,20-triphenylporphyrin.