The effect of the different donor units on fluorescent conjugated polymers containing 2,1,3-benzooxadiazole as the acceptor unit

Date

2015-08-15

Author

Goker, Seza
Hizalan, Gonul
Ileri, Merve
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

222
views

0
downloads

A series of monomers were synthesized via Stille coupling to obtain low-band gap conjugated polymers namely poly(5,6-bis(octyloxy)-4,7-di(thieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]oxadiazole (PTTBO)), poly(5,6-bis(octyloxy)-4,7-di(selenophen-2-yl)benzo[c][1,2,5]oxadiazole (PSBO)) and poly(5,6-bis(octyloxy)-4,7-di(furan-2-yl)benzo[c][1,2,5]oxadiazole (PFBO)) which comprise electron-rich thieno[3,2b]thiophene (TT), selenophene and furan, as the donor units in conjugation with electron-deficient 2,1,3-benzooxadiazole (BO) moiety as the acceptor unit. All three polymers were synthesized electrochemically and well characterized. These polymers exhibited broad spectral absorptions, low-lying highest occupied molecular orbital (-5.71, -5.88, -5.76 eV), and as well as low band gap ranging from 1.45 eV to 1.56 eV. Introducing different donor moieties on the polymer backbone provides to alter the optoelectronic properties.

Subject Keywords

Benzooxadiazole, Stille coupling, Fluorescence, Selenophene, Furan, Thieno[3,2-b]thiophene

URI

https://hdl.handle.net/11511/40334

Journal

JOURNAL OF ELECTROANALYTICAL CHEMISTRY

DOI

https://doi.org/10.1016/j.jelechem.2015.05.028

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

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...
The effect of para-cyclophane structure on cyclacenes Türker, Burhan Lemi (2000-02-01) Semiempirical molecular orbital treatment at the level of AMI type has been performed on the Huckel type cyclacenes having the normal and the skew type para-cyclophane moiety embedded into their structures. The cyclophane effect is found to be operative on the lower members by veiling the cryptoannulenic effect which is influential on the heats of formation values and the frontier molecular orbital energies of the higher members as well as the parent cyclacenes.
The effect of valine substitution for glycine in the dimer interface of citrate synthase from Thermoplasma acidophilum on stability and activity Kocabıyık, Semra (Elsevier BV, 2000-08-28) To determine the role of hydrophobic interactions in the dimer interface of citrate synthase (CS) from Thermoplasma (Tp) acidophilum in thermostabilization, we have used site-directed mutagenesis to replace Gly 196 by Val on the helix L of the subunit interface. Recombinant wild-type and Gly 196 mutant TpCS enzymes were largely identical in terms of substrate specificities (K-m for oxaloacetate and acetyl CoA). However, the mutation not only reduced catalytic activity (about 10-fold) (i.e., V-max, K-cat and...
The use of pyrolysis mass spectrometry to investigate polymerization and degradation processes of methyl amine-based benzoxazine Bagherifam, Shahla; Uyar, Tamer; Ishida, Hatsuo; Hacaloğlu, Jale (2010-06-01) In this study, direct pyrolysis mass spectrometry, DP-MS, was applied to investigate curing and polymerization mechanisms of phenol and methyl amine-based benzoxazine monomer, and thermal decomposition and crosslinking characteristics of the corresponding polybenzoxazine. The results indicated opposing polymerization reaction routes besides the generally accepted one. The cleavage of C-O bonds of the oxazine rings either followed by transformation into a polymer constituting ortho or para substituted phenol...
The impact of [1,2,5]chalcogenazolo[3,4-f]-benzo[1,2,3]triazole structure on the optoelectronic properties of conjugated polymers Alkan, Ecem Aydan; GÖKER, SEZA; Sarigul, Hatice; Yıldırım, Erol; Udum, Yasemin Arslan; Toppare, Levent Kamil (2020-04-01) Two novel conjugated near-infrared (NIR) absorbing donor-acceptor type copolymers comprising benzodithiophene as the donor and [1,2,5]chalcogenazolo[3,4-f]-benzo[1,2,3]triazole derivatives as the acceptors, spaced with thiophene as the pi-bridge, were designed and synthesized via Stille polycondensation reaction. The effect of acceptor strength on optoelectronic properties was targeted and investigated. Branched alkyl chains (the extended 2-octyl-1-dodecyl alkyl chain; -C8C12) were introduced to 5H-[1,2,3]t...

Citation Formats

S. Goker, G. Hizalan, M. Ileri, S. O. Hacioglu, and L. K. Toppare, “The effect of the different donor units on fluorescent conjugated polymers containing 2,1,3-benzooxadiazole as the acceptor unit,” JOURNAL OF ELECTROANALYTICAL CHEMISTRY, pp. 80–89, 2015, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/40334.