Synthesis and electropolymerization of an ion sensing and fluorescent fluorene derivative bearing a quinoxaline moiety and its analogues with different donor units

Date

2012-09-01

Author

KIVRAK, Arif
Carbas, Buket Bezgin
Zora, Metin
Önal, Ahmet Muhtar

Metadata

Show full item record

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

Item Usage Stats

187
views

0
downloads

A series of new fluorene derivatives bearing pendant quinoxaline moieties with different donor groups, namely 5'H-spiro[fluorene-9,4'-pyrrolo[1,2-alquinoxaline] (FQ), 2,7-di(thiophen-2-yl)-5'H-spiro[fluorene-9,4'-pyrrolo[1,2-a]quinoxaline] (TQT), 2,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-5'H-spiro[fluorene-9,4'-pyrrolo[1,2-a]quinoxaline] (EQE) and 2,7-bis(3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4)dioxepin-6-yl)-5'H-spiro[fluorene-9,4'-pyrrolo[1,2-a]quinoxaline] (PQP) were synthesized. The monomers were electropolymerized via potentiodynamic methods in order to understand the effects of donor units on the electrochemical and optoelectronic properties of the resulting polymers. It was found that polymer films exhibit reversible redox behavior accompanied with a reversible electrochromic behavior (E-p(ox) = 0.95 V for poly(2,7-di(thiophen-2-yl)-5'H-spiro[fluorene-9,4'-pyrrolo[1,2-a]quinoxaline]) (PTQT), E-p(ox) = 0.90 V for poly(2,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-5'H-spiro[fluorene-9,4'-pyrrolo[1,2-a]quinoxaline]) (PEQE) and E-p(ox) = 0.67 V for poly(2,7-bis(3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepin-6-yl)-5'H-spiro[fluorene-9,4'-pyrrolo[1,2 a]quinoxaline]) (PPQP)). The band gap values (E-g) of the polymers were found to be 2.47, 1.93 and 1.66 eV for PTQT, PEQE and PPQP, respectively. Furthermore, the ion sensitivity of PQP and its polymer PPQP was also investigated by monitoring the change in the fluorescence intensity. Among various common ions, both PQP and PPQP were found to be selective towards Fe2+ ions by quenching the fluorescence efficiency with a Stern-Volmer constant (K-sv) of (5.9 x 10(3) M-1) and (2.7 x 10(4) M-1) for monomer and polymer solutions, respectively.

Subject Keywords

Materials Chemistry, Biochemistry, General Chemistry, General Chemical Engineering, Polymers and Plastics, Environmental Chemistry

URI

https://hdl.handle.net/11511/39904

Journal

REACTIVE & FUNCTIONAL POLYMERS

DOI

https://doi.org/10.1016/j.reactfunctpolym.2012.06.007

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Synthesis and mesophase properties of block and random co-polymers of electroactive and liquid crystalline monomers Yilmaz, F; Kasapoglu, F; Hepuzer, Y; Yagci, Y; Toppare, Levent Kamil; Fernandes, EG; Galli, G (Informa UK Limited, 2005-01-01) Homo-polymers and random co-polymers of electroactive and liquid crystalline monomers, namely 3-thienylmethyl methacrylate (MTM) and 6-(4-cyanobiphenyl-4'-oxy)hexyl acrylate (LC6), were prepared by conventional free radical polymerization. Block co-polymers of MTM and LC6 were also synthesized by using the 1,1-diphenylethene (DPE) method. The obtained random and block co-polymers exhibited liquid crystal behavior depending on the content of the LC6 units. It was found that microphase separation of the polym...
Synthesis, characterization and electrochromic properties of conducting copolymers of 3-[(3-thienylcarbonyl)oxy]-2,2-bis{[(3-thienylcarbonyl)oxy]}propyl 3-thiophene carboxylate with thiophene and pyrrole Bulut, U; Yilmaz, F; Yagci, Y; Toppare, Levent Kamil (Elsevier BV, 2004-01-01) 3-[(3-Thienylcarbonyl)oxy]-2,2-bis{[(3-thienylcarbonyl)oxy]}propyl 3-thiophene carboxylate (TOTPT) was synthesized by the reaction of 3-thionylcarbonyl chloride with pentaerythritol, it was electrochemically polymerized with either thiophene or pyrrole by using tetrabutylammonium tetrafluoroborate (TBAFB) as the supporting electrolyte in acetonitrile (AN). Characterization of the resulting copolymers was carried out by FTIR spectroscopy, cyclic voltammetry, thermal gravimetry analysis (TGA), differential sc...
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 ...
Synthesis and Characterization of Conducting Copolymers of Bisphenol A-Diglycidyl Ether with Thiophene Side-Groups and Pyrrole Sahmetlioglu, Ertugrul; Varol, Ramazan; Toppare, Levent Kamil; Yuruk, Huseyin (Informa UK Limited, 2009-01-01) Copolymers of bisphenol A-diglycidyl ether with thiophene side-groups and pyrrole were synthesized by electrochemical polymerization. Bisphenol A-diglycidyl ether with thiophene side-groups (DGEBATh) was obtained from the reaction between bisphenol A-diglycidyl ether (DGEBA) and thiophene-3-acetic acid. The syntheses of copolymers of DGEBATh and pyrrole were achieved electrochemically using three different supporting electrolytes, p-toluene sulfonic acid (PTSA), sodium dodecyl sulfate (SDS) and tetrabutylam...
Synthesis and photophysical property of well-defined donor-acceptor diblock copolymer based on regioregular poly(3-hexylthiophene) and fullerene LEE, Jea Uk; Çırpan, Ali; EMRICK, Todd; RUSSELL, Thomas P.; JO, Won Ho (Royal Society of Chemistry (RSC), 2009-03-04) A new, well-defined diblock copolymer (P3HT-b-C60) based on regioregular poly(3-hexylthiophene) (P3HT) and fullerene was synthesized. First, regioregular P3HT was synthesized through Grignard metathesis polymerization, and then methyl methacrylate (MMA) and 2-hydroxyethyl methacrylate (HEMA) were copolymerized by using an end-functionalized P3HT as a macroinitiator for the atom transfer radical polymerization to yield a diblock copolymer (P3HT-b-P(MMA-r-HEMA)). A fullerene derivative functionalized with car...

Citation Formats

A. KIVRAK, B. B. Carbas, M. Zora, and A. M. Önal, “Synthesis and electropolymerization of an ion sensing and fluorescent fluorene derivative bearing a quinoxaline moiety and its analogues with different donor units,” REACTIVE & FUNCTIONAL POLYMERS, pp. 613–620, 2012, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/39904.