Abdurrahman, Nuraddeen
(2024)
Bis-, Tris-, And Tetrakisbenzimidazolium
Salts And Their
Silver(I) Complexes: Synthesis,
Characterization And Biological
Applications.
PhD thesis, Universiti Sains Malaysia.
Abstract
This research describes the synthesis, characterization, crystal structure and
cytotoxicity activity of several new bis-, tris- and tetrakis-benzimidazolium salts, (1-
24) and their respective silver(I)-benzimidazol-2-ylidene complexes, (Ag1-Ag24).
All the compounds synthesized were new based on literature reviewed, it was
achieved by changing the either the alkyl or aryl substituents on the benzimidazolium
systems and or the bridging ligands related to the previously reported compounds.
The salts were synthesized by nucleophilic substitution reaction and were
categorized into five series. The salts were 1-5, 6-9, 10-14, 15-19, 20-24 as first,
second, third, fourth and fifth series respectively. The synthesized salts were utilized
for the synthesis of their respective silver(I)-benzimidazol-2-ylidene complexes, by
in-situ deprotonation method in the presence of silver(I)oxide. The cytotoxicity
potential of the synthesized compounds was carried out by MTT assay method, in
which the breast and cervical cancer cell lines were used. Salt 1-5, 6-9, 15-19, and
their silver(I)-benzimidazol-2-ylidene complexes, (Ag1-Ag5, Ag6 -Ag9, Ag15-Ag19)
were tested against breast cancer cell lines, while salts, 10-14, 20-24, and their
silver(I)-benzimidazol-2-ylidene complexes, (Ag10-Ag14, Ag20-Ag24) were tested
against cervical cancer cell lines. The positive control used for the breast cancer cell
was tamoxifen and etoposide for the cervical cancer cell. All the salts and their
respective silver(I)-benzimidazol-2-ylidene complexes synthesized were
characterized using various characterization techniques including FTIR, 1H, 13C NMR, elemental analysis, and single crystal X-ray diffraction method. Physical
properties were accessed by melting point analysis, and solubility tests in various
organic solvents. From structural elucidation, it was confirmed that Ag2 was
dinuclear silver(I)-benzimidazol-2-ylidene complex, with two PF6 anions as
counterions balancing the charges of the entire molecule. Complex Ag13 confirmed
to be a cylinder-like trinuclear silver(I)-benzimidazol-2-ylidene complex containing
three silver(I) ions bridged by two disc-like ligands.
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