Thieno[2,3-b]thiophene based polymers: Synthesis and optoelectronic properties

[Display omitted] •Cross-conjugated polymers demonstrated bathochromic shifts compared to monomers up to 203 nm.•The smallest/largest Eg were 2.18/2.65 eV for H and NMe2 units, respectively.•Low oxidation potentials of 1.10–1.31 V were recorded.•The experimental results were supported by DFT and TD-...

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Bibliographic Details
Published in:European polymer journal 2018-07, Vol.104, p.72-80
Main Authors: Cinar, M. Emin, Cankaya, Sule Taskiran, Capan, Asli, Eroglu, Mehmet S., Ozturk, Turan
Format: Article
Language:English
Subjects:
Aromatic compounds
Chemical synthesis
Computation
Cyclic voltammetry
Electric properties
Energy gap
Ketones
Nitrogen dioxide
Optical properties
Optoelectronic
Optoelectronics
Oxidation
Photonic band gaps
Polymers
Thieno[2,3-b]thiophene
Thiophenes
UV–Vis
Voltammetry
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Summary:[Display omitted] •Cross-conjugated polymers demonstrated bathochromic shifts compared to monomers up to 203 nm.•The smallest/largest Eg were 2.18/2.65 eV for H and NMe2 units, respectively.•Low oxidation potentials of 1.10–1.31 V were recorded.•The experimental results were supported by DFT and TD-DFT computational studies. Synthesis of novel thieno[2,3-b]thiophenes (TTs) possessing para substituted phenyl groups (Ph–, MeOPh–, BrPh–, NO2Ph–, NH2Ph– and NMe2Ph–) at C-3 has been achieved through ring closure reactions of mono ketones, i.e. 1-aryl-2-(thiophen-2-ylthio)ethan-1-one, and polymerizations of TTs (PhTT (10), p-MeOPhTT (11), p-NO2PhTT (13) and p-NMe2PhTT (18)) under Suzuki coupling condition are demonstrated. The optical and electronic properties of the polymers were investigated systematically. Polymers demonstrated bathochromic shift with respect to their monomers in UV–Vis investigations up to 203 nm for 23 consisting of NO2 unit. While unsubstituted phenyl possessing polymer has the smallest band gap of 2.18 eV, the largest one was noticed to be 2.65 eV for NMe2 containing polymer 24. Electrochemical studies revealed the relatively low oxidation potentials recorded between 1.10 and 1.31 V.
ISSN:0014-3057
1873-1945
DOI:10.1016/j.eurpolymj.2018.05.001