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

Yasa, Mustafa
Toppare, Levent Kamil
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.


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...
Multipurpose selenophene containing conjugated polymers for optoelectronic applications
ONK, Ipek; HIZALAN, Gonul; CEVHER, ŞEVKİ CAN; HACIOGLU, Serife O.; Toppare, Levent Kamil; Çırpan, Ali (Informa UK Limited, 2017-03-04)
In this study, two new conjugated polymers were synthesized including benzotriazole (BTz) as the acceptor unit and selenophene as the bridge donor segment. These acceptors were coupled with fluorene and carbazole via Suzuki condensation reactions. Electrochemical band gaps were calculated as 2.45 eV for P1 and 2.40 eV for P2. Electrochemical and optical studies of polymers indicate that both polymers are promising candidates for organic solar cell (OSC) and polymer organic light emitting diode (PLED) applic...
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...
Polymerization of 2-hydroxyethyl acrylate in bulk and solution by chemical initiator and by ATRP method
Vargun, E; Usanmaz, Ali (Wiley, 2005-09-01)
In this study, 2-hydroxyethyl acrylate (HEA) was polymerized to obtain polymers that can be used as hydrogel and copolymerized for biomedical applications. Bulk, solution, and atom transfer radical polymerization (ATRP) techniques at different temperatures were applied. The polymerization in bulk form was carried out in vacuum and in open atmosphere. The polymerization curves showed autoacceleration mechanism and the limiting conversion was 100%. The polymers obtained were insoluable in most common solvents...
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: