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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
Date
2023-06-29
Author
Çakal, Deniz
Demir Arabacı, Elif
Yıldırım, Erol
Cihaner, Atilla
Önal, Ahmet Muhtar
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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.
Subject Keywords
Donor-acceptor-donor (D-A-D)
,
EDOT
,
Phthalimide (PI)
,
Thieno[3,4-c]pyrrole-4,6,dione (TPD)
,
Thiophene
URI
https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85162225387&origin=inward
https://hdl.handle.net/11511/104557
Journal
Tetrahedron
DOI
https://doi.org/10.1016/j.tet.2023.133473
Collections
Department of Chemistry, Article
Citation Formats
IEEE
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BibTeX
D. Çakal, E. Demir Arabacı, E. Yıldırım, A. Cihaner, and A. M. Önal, “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,”
Tetrahedron
, vol. 140, pp. 0–0, 2023, Accessed: 00, 2023. [Online]. Available: https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85162225387&origin=inward.