Synthesis of some pillar[5]arene compounds and investigation of their use in the detection of toxic anion in CBRN field and intra cellular imaging studies

This thesis aims to detect toxic anions used or likely to be used in chemical, biological, radiological, nuclear and explosions (CBRN+P) fields by using the synthesized macrocyclic compounds Pillar[5]-Bodipy and P5-click-B and to investigate the applicability of this detection process in intracellular imaging studies. Agents used or likely to be used in CBRN+P cases have toxic effects on health and ecosystems, and toxic anions are also present among these agents. Therefore, it is of great importance to detect toxic anions, which have the potential to have adverse effects on ecosystem and human health and can be used in the CBRN+P field, with an effective sensor system. In order to detect toxic anions, two different sensors, named Pillar[5]-Bodipy and P5-click-B, containing multiple Bodipy units based on the structure of the macrocyclic compound Pillar[5]arene (P[5]A), were synthesized in this study. The characterization of the synthesized unsymmetrical P[5]A derivative Pillar[5]-Bodipy and P5-click-B macrocyclic sensors was carried out by NMR (Nuclear Magnetic Resonance), FT-IR (Fourier Transform Infrared Spectroscopy), elemental analysis and melting point determination methods. During the interaction between the synthesized Pillar[5]-Bodipy probe and toxic anions, a strong emission occurs at a wavelength of 510 nm, while during the interaction between the P5-click-B probe and toxic anions, a strong emission occurs at a wavelength around 550 nm. The selectivity performance of the synthesized chemosensors against different anions was investigated using competing ion tests. As a result of these tests, a significant suppression of the fluorescence intensity was observed only for F⁻ anions in the study conducted with the Pillar[5]-Bodipy probe, and only for H2PO4⁻ anions in the study conducted with the P5-click-B probe. However, no significant change was observed in the fluorescence intensity of other test ions. The fluorescence intensity of the Pillar[5]-Bodipy macrocyclic probe decreased significantly in the presence of F− anion and the LOD was determined as 2.1x10-7 M. The fluorescence intensity of the P5-click-B macrocyclic probe decreased significantly in the presence of H2PO4⁻ anion and the LOD was determined as 4,51x10-8 M. As a result of the studies, it was determined that the Pillar[5]-Bodipy sensor had an ideal response time for the detection of F− anion, and the P5-click-B sensor had an ideal stability in various pH ranges for the detection of H2PO4⁻ anion. Intracellular imaging studies of the Pillar[5]-Bodipy and P5-click-B sensors were also performed, and the F− anion was successfully detected with the Pillar[5]-Bodipy sensor, and the H2PO4⁻ anion was successfully detected with the P5-click-B sensor in the cell. Additionally, the toxic effects of the chemosensor on identified cancer cells were also investigated. Consequently, the Pillar[5]-Bodipy and P5-click-B macrocyclic probes were found to exhibit low toxicity. The Pillar[5]-Bodipy sensor was successfully used for the recognition of F− anions in living cells, while the P5-click-B sensor was successfully used for the recognition of H2PO4⁻ anions in living cells. The probes' prominent features include their turn-off response, rapid and selective detection properties, wide pH ranges, and suitability for bioimaging studies.