Effect of fluorine substituted benzothiadiazole on electro-optical properties of donor-acceptor-donor type monomers and their polymers

A series of trimeric monomers bearing thiophene donor units and fluorinated analogues of benzothiadiazole acceptor units was synthesized via donor-acceptor-donor approach and polymerized electrochemically in order to investigate the effect of fluorine atom on electro-optical properties of both monomers and their corresponding polymers. All monomers exhibited solvatochromic and fluorescent properties. The introduction of fluorine atom into the conjugated backbone increased the oxidation potentials. Upon moving from nonfluorinated to fully fluorinated analogues, the oxidation potential shifts anodically from 1.30 V to 1.7 V. As in the case of monomers, the fluorine atom substitution also resulted in a decrease in the HOMO energy level of the corresponding polymers, leading to an increase in the electrochemical band gap energy (1.71-1.97 eV). This result can be attributed to deviations from planarity and also to decrease in the effective conjugation length. The polymeric film also exhibited electrochromic properties under various external potentials. Switching time and coloration efficiency values decreased with increasing number of fluorine atom substitution.


Synthesis and electrochemical polymerization of D-A-D type monomers with thieno [3,4-c] pyrrole-4,6-dione acceptor unit
Çakal, Deniz; Cihaner, Atilla; Önal, Ahmet Muhtar (Elsevier BV, 2018-11-01)
In this study, three new donor-acceptor-donor type monomers bearing 1,3-dibromo-5-(2-ethylhexyl)-4H-thieno [3,4-c]pyrrole- 4,6(5H)-dione (A) as an acceptor unit and thiophene, 3,4-ethylenedioxythiophene (EDOT) and 3,3-didecy1-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine (didecyl-ProDOT) as donor units were synthesized via Stille cross-coupling reaction and their electrochemical polymerization by repetitive cycling was reported. The electrochemical and optical properties of the monomers ((5-(2-ethyl-liexyl)-1,...
BATTAL, T; BAC, N; Yılmaz, Levent (Informa UK Limited, 1995-01-01)
An emerging membrane morphology with future potential is mixed matrix membranes composed of two interpenetrating matrices of different materials. In this study, mixed matrix membranes of an amorphous glassy polymer(polyethersulfone) and hydrophilic zeolite (4A) were prepared. An elaborate membrane preparation technique that enables incorporation of high zeolite loading into the membrane was developed. Performance of membranes was tested by using a laboratory-scale gas separation apparatus. The permeation ra...
Effect of the donor units on the properties of fluorinated acceptor based systems
Önal, Ahmet Muhtar; Akdağ, Akın; Çakal, Deniz (Elsevier BV, 2020-10-01)
A new series of monomers in the donor-acceptor-donor array, namely 5-fluoro-4,7-di(furan-2-yl)benzo[c][1,2,5]thiadiazole (F2BT-F), and 5-fluoro-4,7-di(selenophen-2-yl)benzo[c][1,2,5] thiadiazole (S2BT-F), bearing 5-fluorobenzo[c][1,2,5]-thiadiazole as the acceptor moiety and furan and selenophene as the electron donating groups was synthesized and polymerized electrochemically. To compare heteroatom effect, thiophene analogue of newly synthesized F2BT-F and S2BT-F namely, (5-fluoro-4,7-di(thiophen-2-yl)benz...
Effect of Alkyl Derivatization on Several Properties of N-Halamine Antimicrobial Siloxane Coatings
Kocer, Hasan B.; Akdağ, Akın; Ren, Xuehong; Broughton, R. M.; Worley, S. D.; Huang, T. S. (American Chemical Society (ACS), 2008-10-01)
Variation of alkyl substitution at position 5 on the hydantoin ring of a series of N-halamine siloxane derivatives has been employed to better understand the biocidal activities of these compounds for use in preparing antimicrobial coatings. The alkyl derivatization of the hydantoin ring at its 5 position, while an essentially constant chlorine loading is maintained at the I position, has shown that there is little dependence of the antimicrobial efficacy against Escherichia coli O157:H7 on the alkyl chain ...
Electrochemical and optical properties of substituted phthalimide based monomers and electrochemical polymerization of 3,4-ethylenedioxythiophene-polyhedral oligomeric silsesquioxane (POSS) analogue
Çakal, Deniz; Cihaner, Atilla; Önal, Ahmet Muhtar (Elsevier BV, 2019-02-01)
A new series of donor-acceptor-donor type trimeric monomers bearing substituted phthalimide units as acceptor units and thiophene and 3,4-ethylenedioxythiophene (EDOT) as donor units was synthesized and characterized. The strength of acceptor units and intramolecular charge transfer between donor and acceptor units were investigated by using electrochemical and optical methods. The main advantage of phthalimide unit over other acceptor units is the ease of its functionalizability. Thus, utilizing this prope...
Citation Formats
D. Çakal and A. M. Önal, “Effect of fluorine substituted benzothiadiazole on electro-optical properties of donor-acceptor-donor type monomers and their polymers,” DYES AND PIGMENTS, pp. 0–0, 2020, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/47897.