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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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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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Acknowledgments

We are grateful to Aksaray University (ASU BAP 2015-092), Atilim University (ATU-BAP-A-1314-03, ATU-BAP-1011-05) and the Scientific and Technological Research Council of Turkey (TUBITAK, Grant No. 109R009) for partial financial support of our projects. European Cooperation in Science and Technology (COST) and Turkish Academy of Sciences (TUBA) are also gratefully acknowledged. Z. O. is indebted to TUBITAK for a graduate fellowship.

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Authors and Affiliations

  1. Health Services Vocational School & ASUBTAM BioNanoTech Lab, Aksaray University, 68100, Aksaray, TR, Turkey

    Melek Pamuk Algi

  2. Department of Biotechnology and Molecular Biology & ASUBTAM BioNanoTech Lab, Aksaray University, 68100, Aksaray, TR, Turkey

    Zahide Oztas & Fatih Algi

  3. Chemical Engineering and Applied Chemistry, Atilim University, 06836, Ankara, TR, Turkey

    Seha Tirkeş

  4. Atilim Optoelectronic Materials and Solar Energy Laboratory (ATOMSEL), Chemical Engineering and Applied Chemistry, Atilim University, 06836, Ankara, TR, Turkey

    Atilla Cihaner

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  1. Melek Pamuk Algi
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  2. Zahide Oztas
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Correspondence to Atilla Cihaner or Fatih Algi.

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Supplementary information associated with this article (copies of 1H, 13C NMR and HRMS spectra) can be found in the online version.

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Algi, M.P., Oztas, Z., Tirkeş, S. et al. Atomistic Engineering of Chemiluminogens: Synthesis, Properties and Polymerization of 2,3-Dihydro-Pyrrolo[3,4-d]Pyridazine-1,4-Dione Scaffolds. J Fluoresc 27, 509–519 (2017). https://doi.org/10.1007/s10895-016-1978-x

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