You are cordially invited to attend the seminar organized by the Department of Chemistry.
Title: Fluorogenic Tetrazines and Chiral Fluorophores: Synthesis, Structure, and (Chir)Optical Behavior
Speaker: Prof. Murat Işık
Date: 28/10/2025, Tuesday
Time: 12:30 (Turkiye Time)
This is an online seminar. To request event details please send a message to department.
Fluorogenic Tetrazines and Chiral Fluorophores: Synthesis, Structure, and (Chir)Optical Behavior
Fluorophores bearing a 1,2,4,5-tetrazine (s-tetrazine, Tz) motif have become invaluable tools for visualizing and tracking biomolecules. However, complex syntheses and challenging purifications have limited their accessibility. To address these issues, we developed a straightforward nucleophilic aromatic substitution (SNAr) approach that couples commercially available amino-tetrazines (TzH, TzMe) with several halo-fluorophores. The resulting charge-neutral, color-tunable Tz-fluorophores exhibit high fluorogenicity, large Stokes shifts, and moderate environmental sensitivity. Upon reaction with bicyclononyne (BCN)—a strained dienophile used in bioorthogonal chemistry—they display up to a 193-fold fluorescence enhancement. Successful labeling of BCN-modified human serum albumin yielded bright blue–green emission, demonstrating their strong potential as accessible and high-contrast fluorogenic probes for bioconjugation.
The second part of the talk focuses on our recent works toward chiral fluorophores. First, a serendipitious discovery of a boron dipyrromethene chiral at boron and carbon (BC–BODIPY), accessed through an interrupted Knoevenagel condensation, will be presented. Next, a multicomponent synthesis leading to a new family of boron-stereogenic BOSPYR fluorophores is going to be shortly discussed. Cumulative data from X-ray crystallography, fluorescence lifetime, and viscosity-dependent emission experiments, among others, were used to gain insight into the fluorescence and chiroptical behavior of these dyes in relation to their molecular structures.
Short Biography:
Dr. Murat Işık received his B.S., M.S., and Ph.D. degrees in Chemistry from Middle East Technical University (METU). Following his doctoral studies under the supervision of Prof. Dr. Cihangir Tanyeli, he conducted postdoctoral research at UNAM—Institute of Materials Science and Nanotechnology, Bilkent University, working with Prof. Dr. Engin U. Akkaya. He joined Bingöl University in 2014, where he is currently a Professor in the Department of Food Engineering and serves as the Coordinator of the Scientific Research Projects (BAP) Unit. His research interests include molecular recognition, organocatalytic enantioselective synthesis, and new reaction development, with a particular focus on the design of fluorescent probes for bioconjugation and food safety, chiral catalysts, and chiral dyes. He is also a member of the American Chemical Society (ACS).