article.page.titleprefix Effect of phthalimide and thieno[3,4-c]pyrrole-4,6,dione acceptors on π-conjugated donor-acceptor-donor monomers: Experimental and theoretical investigations of photophysical and electrochemical properties
| dc.contributor.author | Çakal, Deniz | |
| dc.contributor.author | Demir Arabacı, Elif | |
| dc.contributor.author | Yıldırım, Erol | |
| dc.contributor.author | Cihaner, Atilla | |
| dc.contributor.author | Önal, Ahmet M. | |
| dc.date.accessioned | 2024-01-16T13:34:16Z | |
| dc.date.available | 2024-01-16T13:34:16Z | |
| dc.date.issued | 2023-06-29 | |
| dc.description | Published by Tetrahedron; https://doi.org/10.1016/j.tet.2023.133473; Deniz Çakal, Elif Demir Arabacı, Erol Yildirim, Ahmet M. Önal, Department of Chemistry, Middle East Technical University, Ankara, 06800, Turkey; Deniz Çakal, Erol Yildirim, Department of Micro and Nanotechnology, Middle East Technical University, Ankara, 06800, Turkey; Erol Yildirim, Department of Polymer Science and Technology, Middle East Technical University, 06800, Ankara, Turkey; Atilla Cihaner, Atilim Optoelectronic Materials and Solar Energy Laboratory (ATOMSEL), Department of Chemical Engineering, Atilim University, TR-06830 Ankara, Turkey. | |
| dc.description.abstract | In this study, two novel donor-acceptor-donor monomers were synthesized by coupling a phthalimide (PI) acceptor unit with thiophene (T) and ethylenedioxythiophene (EDOT (E)) donor units. These two novel PI-based monomers, namely 2-(2-ethylhexyl)-4,7-di(thiophen-2-yl)isoindoline-1,3-dione (T-PI) and 4,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-2-(2-ethylhexyl)isoindoline-1,3-dione (E-PI), were fully characterized via UV-vis and fluorescence spectroscopy as well as electrochemical methods, and the results were directly compared with those of previously synthesized thieno[3,4-c]pyrrole-4,6-dione (TPD)-based analogues to report the results for four classes of monomers. In this regard, the effects of different donor groups and structural modifications in the acceptor unit as changed from PI to TPD have been investigated to reveal the precise effect of the donor and acceptor on the optical and electrochemical properties of the monomers. All monomers exhibits an intramolecular charge transfer band in the low energy region due to strong donor and acceptor interactions. The oxidation and reduction potentials of the monomers are found to vary depending on the strengths of both donor and acceptor units. PI-based monomers show more positive oxidation and less negative reduction potentials than TPD-based analogues. Similarly, thiophene-based analogues reveal the same trend in their oxidation and reduction potentials as compared to EDOT-based analogues. Lastly, PI-based monomers could not undergo polymerization via electrochemical method, unlike TPD-based monomers, since the dihedral angle arising between donor and PI acceptor disturbs molecular planarity significantly, as demonstrated by first principle calculations. | |
| dc.description.sponsorship | 2232 International Fellowship for Outstanding Researchers Program of TÜBİTAK (Project No: 118C251). The calculations reported in this paper were partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA) and National Center for High Performance Computing of Turkey (UHeM) under grant number 1008192020. | |
| dc.identifier.citation | http://hdl.handle.net/20.500.14411/1964 | |
| dc.identifier.issn | 1464-5416 | |
| dc.identifier.uri | https://doi.org/10.1016/j.tet.2023.133473 | |
| dc.language.iso | en | |
| dc.publisher | Tetrahedron | |
| dc.relation.ispartofseries | 140 | |
| dc.subject | Thieno[3,4-c]pyrrole-4,6,dione (TPD); Phthalimide (PI); Donor-acceptor-donor (D-A-D) Thiophene; EDOT | |
| dc.title | Effect of phthalimide and thieno[3,4-c]pyrrole-4,6,dione acceptors on π-conjugated donor-acceptor-donor monomers: Experimental and theoretical investigations of photophysical and electrochemical properties | |
| dc.type | Article | |
| dspace.entity.type | Article |