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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dc.authoridAlgi, Fatih -- 0000-0001-9376-1770
dc.contributor.authorPamuk Algı, Melek
dc.contributor.authorÖztaş, Zahide
dc.contributor.authorTirkeş, Seha
dc.contributor.authorCihaner, Atilla
dc.contributor.authorAlgı, Fatih
dc.date.accessioned13.07.201910:50:10
dc.date.accessioned2019-07-29T19:30:08Z
dc.date.available13.07.201910:50:10
dc.date.available2019-07-29T19:30:08Z
dc.date.issued2017
dc.departmentSabire Yazıcı Fen Edebiyat Fakültesi
dc.description.abstractTwo 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 (E-g) 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.
dc.description.sponsorshipAksaray University [ASU BAP 2015-092]; Atilim University [ATU-BAP-A-1314-03, ATU-BAP-1011-05]; Scientific and Technological Research Council of Turkey (TUBITAK) [109R009]; TUBITAK
dc.description.sponsorshipWe 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.
dc.identifier.doi10.1007/s10895-016-1978-x
dc.identifier.endpage519en_US
dc.identifier.issn1053-0509
dc.identifier.issn1573-4994
dc.identifier.issue2en_US
dc.identifier.pmid27864701
dc.identifier.scopusqualityQ3
dc.identifier.startpage509en_US
dc.identifier.urihttps://doi.org/10.1007/s10895-016-1978-x
dc.identifier.urihttps://hdl.handle.net/20.500.12451/6242
dc.identifier.volume27en_US
dc.identifier.wosWOS:000395070900013
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherSpringer/Plenum Publishers
dc.relation.ispartofJournal of Fluorescence
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectChemiluminescence
dc.subjectPyridazine
dc.subjectThiophene
dc.subject2,5-di(thien-2-yl)pyrrole
dc.subjectElectrochromism
dc.titleAtomistic engineering of chemiluminogens: Synthesis, properties and polymerization of 2,3-dihydro-pyrrolo[3,4-d]pyridazine-1,4-dione scaffolds
dc.typeArticle

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