Atomistic Engineering of Chemiluminogens: Synthesis,Properties and Polymerization of 2,3-Dihydro-Pyrrolo[3,4-d]Pyridazine-1,4-Dione Scaffolds |
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| Authors: | Melek Pamuk Algi Zahide Oztas Seha Tirkeş Atilla Cihaner Fatih Algi |
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| Affiliation: | 1.Health Services Vocational School & ASUBTAM BioNanoTech Lab,Aksaray University,Aksaray,Turkey;2.Department of Biotechnology and Molecular Biology & ASUBTAM BioNanoTech Lab,Aksaray University,Aksaray,Turkey;3.Chemical Engineering and Applied Chemistry,Atilim University,Ankara,Turkey;4.Atilim Optoelectronic Materials and Solar Energy Laboratory (ATOMSEL), Chemical Engineering and Applied Chemistry,Atilim University,Ankara,Turkey |
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| Abstract: | Two chemiluminescent compounds containing 2,5-di(thien-2-yl)pyrrole and pyridazine units, namely 5,7-di(thiophen-2-yl)-2,3-dihydro-1H-pyrrolo[3,4-d]pyridazine-1,4(6H)-dione (5) and 6-phenyl-5,7-di(thiophen-2-yl)-2,3-dihydro-1H-pyrrolo[3,4-d]pyridazine-1,4(6H)-dione (6), were successfully synthesized and electrochemically polymerized. The compounds have chemiluminescent properties and glow in the presence of hydrogen peroxide in basic medium. The intensity of the glow can be increased dramatically by using Fe3+ ions, hemin (1.0 ppm) or blood samples (1.0 ppm) as catalyst. The compounds 5 and 6 have one well-defined irreversible oxidation peak at 1.08 V and 1.33 V vs Ag/AgCl, respectively. Electrochemical polymerization of both 5 and 6 were carried out successfully by repeating potential scanning in the presence of BF3. Et2O in an electrolyte solution of 0.1 M LiClO4 dissolved in acetonitrile. The electronic band gaps (Eg) of the polymers P5 and P6 were found to be 2.02 eV and 2.16 eV, respectively. On the other hand, the corresponding polymers are electroactive and exhibited electrochromic features. |
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