Selenophene-bearing low-band-gap conjugated polymers: tuning optoelectronic properties via fluorene and carbazole as donor moieties

Date

2020-05-01

Author

Yasa, Mustafa
GÖKER, SEZA
Toppare, Levent Kamil

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

147
views

136
downloads

In this study, two donor-acceptor (D-A)-type conjugated polymers, namely PQSeCz and PQSeFl, were designed and synthesized. Selenophene was incorporated as the pi-bridge and quinoxaline as an acceptor unit, while carbazole and fluorene were used as the donor units. Polymers were synthesized via palladium-catalyzed Suzuki polymerization reaction. All molecules were characterized by H-1 and C-13 NMR spectroscopy. The weight and number average molecular weights of the two polymers were determined by gel permeation chromatography. Electrochemical and spectroelectrochemical characterizations of the polymers were performed to investigate their optoelectronic properties. Oxidation potentials were 1.15 V/0.82 V and 1.11 V/0.82 V for PQSeCz and PQSeFl, respectively, while reduction potentials were - 1.26 V/- 1.14 V and - 1.48 V/- 1.20 V, respectively. In the visible region, maximum absorption wavelengths for the two polymers were 551 nm and 560 nm, respectively. Optical band gaps (Egop) were found from the lowest energy pi-pi* transition onsets as 1.67 eV for PQSeCz and 1.51 eV for PQSeFl, respectively. Both polymers showed good solubility in common solvents.

Subject Keywords

Materials chemistry, General chemistry, Polymers and plastics, Condensed matter physics, Conjugated polymer, Quinoxaline, Selenophene, Fluorene, Carbazole, Band gap, Suzuki coupling

URI

https://hdl.handle.net/11511/38299

Journal

POLYMER BULLETIN

DOI

https://doi.org/10.1007/s00289-019-02872-2

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Silafluorene-based polymers for electrochromic and polymer solar cell applications ERLIK, Ozan; UNLU, Naime A.; HIZALAN, Gonul; HACIOGLU, Serife O.; COMEZ, Seda; Yildiz, Esra D.; Toppare, Levent Kamil; Çırpan, Ali (Wiley, 2015-07-01) In this study, four novel silafluorene (SiF) and benzotriazole (Btz) bearing conjugated polymers are synthesized. In the context of electrochemical and optical studies, these polymers are promising materials both for electrochromic device (ECD) and polymer solar cell (PSC) applications. All of the polymers are ambipolar (both p- and n-dopable) and multichromic. Electrochemistry experiments indicate that incorporation of selenophene instead of thiophene unit increases the HOMO energy level of the polymers. P...
Fused structures in the polymer backbone to investigate the photovoltaic and electrochromic properties of donoracceptor-type conjugated polymers CEVHER, ŞEVKİ CAN; UNLU, Naime Akbasoglu; OZELCAGLAYAN, Ali Can; APAYDIN, Dogukan Hazar; Udum, Yasemin Arslan; Toppare, Levent Kamil; Çırpan, Ali (Wiley, 2013-05-01) In this study, two new benzotriazole (BTz) and dithienothiophene (DTT) containing conjugated polymers were synthesized. After successful characterizations of the monomers by proton-nuclear magnetic resonance (1H NMR) and carbon-NMR (13C NMR) techniques, poly(4-(dithieno[3, 2-b:2,3-d]thiophen-2-yl)-2-(2-octyldodecyl)-2H-benzo[d][1,2,3] triazole) P1 and poly(4-(5-(dithieno[3,2-b:2,3-d]thiophen-2-yl)thiophen-2-yl)-2-(2-octyldodecyl)-7-(thiophen-2-yl)-2H-benzo[d][1,2,3]triazole) P2 were synthesized via a typica...
Electrochemical synthesis of new conjugated polymers based on carbazole and furan units Oguzturk, H. Esra; TİRKEŞ, SEHA; Önal, Ahmet Muhtar (2015-08-01) In this study, synthesis of four new monomers; 3,6-di(2-furyl)-9H-carbazole (M1), 3,6-di(2-furyl)-9-ethyl-carbazole (M2), 2,7-di(2-furyl)-9-H-carbazole (M3), 2,7-di(2-furyl)-9-(tridecan-7-yl)-9H-carbazole (M4), was achieved via Stifle cross-coupling reaction. The monomers were electrochemically polymerized, via repetitive cycling in acetonitrile-tetrabutylammonium hexafluorophosphate electrolytic medium. Optical and electrochemical properties of the monomers and their corresponding polymers were investigate...
Alkyl end group Modification of Benzotriazole and Thiophene Containing Conjugated Polymers Cevher, Şevki Can; Keleş, Duygu; Özdemir Hacıoğlu, Şerife; Toppare, Levent Kamil; Çırpan, Ali (null; 2016-07-21) This study focused on modifying the alkyl‐end‐group of benzotriazole and thiophene containing conjugated polymers. Introducing a moiety with struc‐turally rigid and tendency to enhance the π‐π stacking and also absorption in the high energetic region, influence the both electronic and optic properties of the conjugated polymers. Stille cross coupling chemical polymerization method was performed to synthesize the polymer contains: benzotriazole and bisthiophene. Characterizations of polymers were done in ter...
Immobilization of invertase and glucose oxidase in conducting H-type polysiloxane/polypyrrole block copolymers Gursel, A; Alkan, S; Toppare, Levent Kamil; Yagci, Y (Elsevier BV, 2003-01-01) In this study, immobilizations of enzymes, invertase and glucose oxidase, were achieved in conducting copolymers of N-pyrrolyl terminated polydimethylsiloxane/polypyrrole (PDMS/PPy) matrices via electrochemical polymerization. The kinetic parameters, v(max) (maximum reaction rate) and K-m (substrate affinity), of both free and immobilized enzymes were determined. The effect of supporting electrolytes, p-toluene sulfonic acid and sodium dodecyl sulfate, on enzyme activity and film morphologies was examined. ...

Citation Formats

M. Yasa, S. GÖKER, and L. K. Toppare, “Selenophene-bearing low-band-gap conjugated polymers: tuning optoelectronic properties via fluorene and carbazole as donor moieties,” POLYMER BULLETIN, pp. 2443–2459, 2020, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/38299.