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

2017-02-01
Isik, Ebru
Goker, Seza
Hizalan, Gonul
Hacioglu, Serife O.
Toppare, Levent Kamil
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.
JOURNAL OF ELECTROANALYTICAL CHEMISTRY

Suggestions

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...
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...
Preparation and Comparison of Two Electrodes for Supercapacitors: Pani/CNT/Ni and Pani/Alizarin-Treated Nickel
Koysuren, Ozcan; Du, Chunsheng; Pan, Ning; Bayram, Göknur (Wiley, 2009-07-15)
Polyaniline in emeraldine form was synthesized in the presence of multiwalled carbon nanotubes (CNTs), and the electrochemical capacitance performance of thus formed composite as electrode material has been Studied. The polyaniline/carbon nanotubes (Pani/CNT) composite is found to result in a higher specific capacitance than that of either composite constituent, attributable to the double-layer capacitance behavior of the nanotubes in the Pani/CNT system. However, once assembled into a two-electrode cell, l...
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.