Random copolymers of 1,2,3-benzotriazole and alkoxy-modified naptho[2,3-b:3,4-b ']dithiophene: Syntheses, characterization and optoelectronic properties

Date

2017-02-01

Author

Isik, Ebru
Goker, Seza
Hizalan, Gonul
Hacioglu, Serife O.
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

80
views

0
downloads

Naphthodithiophene is a thiophene fused naphthalene with a rigid and planar structure with extended pi-conjugation system and due its electron rich nature it has been recently employed in donor -acceptor type conducting polymers. In this study, alkoxy functionalized naphthodithiophene bearing two new random copolymers namely poly4-(5 ''-(5,6-bis(dodecyloxy)naphtho[2,1-b:3,4-b']dithiophen-2-yl)-[2,2':5',2 ''-terthiophen]-5-yl)-2-dode-cyl-7-(thiophen-2-yl)-2H-benzo[d] [1,2,3]triazole (P1) and poly4-(5 ''-(5,6-bis(dodecyloxy)naphtho[2,1-6:3,4b']dithiophen-2-yl)-[2,2':5',2 '':5 '',2 '':5"',2 ''''-guinguethiophen]-5-yl)-2-dodecy1-7-(thiophen-2-yl)-2H-benzo[d] [1,2,3]triazole (P2) were synthesized via Stille coupling reaction in order to monitor the effect of thiophene and bithiophene bridge units on electrochemical and optical properties of the corresponding polymers. As the acceptor moiety in the polymer backbone electron deficient benzotriazole moiety was used. Thiophene and bithiophene units were used as pi-linkers to enhance electron delocalization through polymer chain. Via alkoxy modification, synthesized polymers were highly soluble in common solvents like THF, chloroform, chlorobenzene. Altering it bridge from thiophene bridge to bithiophene, kinetic properties of the polymers were improved. Electrochemical studies revealed that while P1 has only p-dopable nature, P2 has ambipolar character. Change of pi-bridge from thiophene to bithiophene has affected the optoelectronic properties of the polymers in a favorable manner for different application areas. The polymers exhibited low lying highest occupied molecular orbital (-5.40 eV for P1 and -5.30 eV for P2) and moderate band gaps which are 2.05 eV and 2.02 eV for P1 and P2, respectively.

Subject Keywords

Naphthodithiophene, Benzotriazole, pi-Bridge, Random copolymer, Optoelectronic properties

URI

https://hdl.handle.net/11511/33348

Journal

JOURNAL OF ELECTROANALYTICAL CHEMISTRY

DOI

https://doi.org/10.1016/j.jelechem.2017.01.010

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Syntheses, spectroelectrochemical and electrochemical characterizations of naphthodithiophene containing polymers for solar cell applications Işık, Ebru; Toppare, Levent Kamil; Department of Chemistry (2016) Naphthodithiophene is a thiophene fused naphthalene with a rigid and planar structure with extended π-conjugation system. Due its electron rich nature it has been recently employed in donor-acceptor type conducting polymers which are used as active layers in organic solar cells and organic field effect transistors. In this study alkoxy functionalized naphthodithiophene bearing two new random copolymers were designed and synthesized. As acceptor moiety in the polymer backbone electron deficient benzotriazole...
Novel poly(2,5-dithienylpyrrole) (PSNS) derivatives functionalized with azobenzene, coumarin and fluorescein chromophore units: spectroelectrochemical properties and electrochromic device applications Yigit, Deniz; Hacioglu, Serife O.; GÜLLÜ, Mustafa; Toppare, Levent Kamil (2015-01-01) Three novel 2,5-dithienylpyrrole (SNS) derivatives containing strong chromophore units such as azobenzene, coumarin and fluorescein were synthesized to investigate the effects of chromophore substituents on the electrochemical and spectroelectrochemical properties of resulting polymers. Electrochemical and optoelectronic characteristics of the homopolymers, poly(1-(2-(4-(phenyldiazenyl)phenoxy)ethyl)-2,5di(thiophen-2-yl)-1H-pyrrole) (PTPTAz), poly(4-(2-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)ethoxy)-2H-chrome...
Photo- and electroluminescent properties of a π-conjugated copolymer containing 2,2′-bipyridyl units Deichmann, Vitor Angelo Fonseca; Çırpan, Ali; KARASZ, Frank E.; AKCELRUD, Leni (Wiley, 2007-02-01) The synthesis, structural characteristics, and photo- and electroluminescent properties of a soluble light-emitting copolymer built up of regularly alternating segments of 1,4-dihexyloxybenzene and 2,2'-bipyridyl (PBPyDHB) are described and discussed. Optical properties of the polymer were investigated in solution and solid-state conditions, demonstrating that in film form the predominant emission centers are inter-macromolecular aggregates, either in photo- or electroluminescence. Thermogravimetric analysi...
Sensitivity improvement for antimony determination by using in-situ atom trapping in a slotted quartz tube and flame atomic absorption spectrometry TİTRETİR DURAN, SERAP; Sik, Ahmet Inanc; ARSLAN, YASİN; Ataman, Osman Yavuz (2012-11-01) Significant improvement has been achieved for antimony determination using a slotted quartz tube (SQT) as an atom trap (AT) for in situ preconcentration and flame atomic absorption spectrometry (FAAS). The suggested technique consists of trapping analyte species during ordinary nebulization followed by releasing the collected analyte via introducing organic solvent. Procedures and analytical figures of merit have been presented for the techniques called FAAS. SQT-FAAS and finally SQT-AT-FMS with the relevan...
Synthesis of a novel fluorescent and ion sensitive monomer bearing quinoxaline moieties and its electropolymerization Carbas, Buket Bezgin; KIVRAK, Arif; Zora, Metin; Önal, Ahmet Muhtar (Elsevier BV, 2011-05-01) A novel terthienyl based fluorescent polymer bearing pendant quinoxaline moieties directly attached to the 3-positions of the central thiophene ring was synthesized by electrochemical polymerization of 4-((2,5-dithiophen-2-yl)thiophen-3-yl)pyrrolo[1,2-a]quinoxaline (TT-Q). The corresponding polymer was characterized by cyclic voltammetry, FT-IR and UV-vis spectroscopy. The polymer exhibits a reversible redox behavior (Ep(1/2) = 1.05 V) accompanied with a reversible electrochromic behavior; yellowish orange ...

Citation Formats

E. Isik, S. Goker, G. Hizalan, S. O. Hacioglu, and L. K. Toppare, “Random copolymers of 1,2,3-benzotriazole and alkoxy-modified naptho[2,3-b:3,4-b ’]dithiophene: Syntheses, characterization and optoelectronic properties,” JOURNAL OF ELECTROANALYTICAL CHEMISTRY, pp. 50–57, 2017, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/33348.