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

M. Emin Cinar; Sule Taskiran Cankaya; Asli Capan; Mehmet S. Eroglu; Turan Ozturk

doi:10.1016/j.eurpolymj.2018.05.001

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

M. Emin Cinar^*
, Sule Taskiran Cankaya
, Asli Capan
, Mehmet S. Eroglu
, Turan Ozturk

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University
University of Siegen
Marmara University
Scientific and Technological Research Council of Turkey

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	72-80
Number of pages	9
Journal	European Polymer Journal
Volume	104
DOIs	https://doi.org/10.1016/j.eurpolymj.2018.05.001
Publication status	Published - Jul 2018

Bibliographical note

Publisher Copyright:
© 2018 Elsevier Ltd

Funding

We thank The Scientific and Technological Research Council of Turkey ( TUBITAK ) for supporting this work ( 111T075 ). M. Emin Cinar is grateful to TUBITAK for Postdoctoral Research Fellowships BIDEB 2216 program. We are indebted to National Center for High Performance Computing (UYBHM) (tvddvb) and the High-Performance-Computing (HPC) Linux Cluster HorUS of University of Siegen for the computer time provided. Unsped Global Logistic is gratefully acknowledged for financial support. Appendix A

Funders	Funder number
TUBITAK	111T075
National Council for Scientific Research

Keywords

Computation
Cyclic voltammetry
Optoelectronic
Thieno[2,3-b]thiophene
UV–Vis

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10.1016/j.eurpolymj.2018.05.001

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@article{4111e0254cf74295a8ca982ac831fa3f,

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

abstract = "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.",

keywords = "Computation, Cyclic voltammetry, Optoelectronic, Thieno[2,3-b]thiophene, UV–Vis",

author = "Cinar, \{M. Emin\} and Cankaya, \{Sule Taskiran\} and Asli Capan and Eroglu, \{Mehmet S.\} and Turan Ozturk",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

month = jul,

doi = "10.1016/j.eurpolymj.2018.05.001",

language = "English",

volume = "104",

pages = "72--80",

journal = "European Polymer Journal",

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TY - JOUR

T1 - Thieno[2,3-b]thiophene based polymers

T2 - Synthesis and optoelectronic properties

AU - Cinar, M. Emin

AU - Cankaya, Sule Taskiran

AU - Capan, Asli

AU - Eroglu, Mehmet S.

AU - Ozturk, Turan

PY - 2018/7

Y1 - 2018/7

N2 - 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.

AB - 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.

KW - Computation

KW - Cyclic voltammetry

KW - Optoelectronic

KW - Thieno[2,3-b]thiophene

KW - UV–Vis

UR - https://www.scopus.com/pages/publications/85046760154

U2 - 10.1016/j.eurpolymj.2018.05.001

DO - 10.1016/j.eurpolymj.2018.05.001

M3 - Article

AN - SCOPUS:85046760154

SN - 0014-3057

VL - 104

SP - 72

EP - 80

JO - European Polymer Journal

JF - European Polymer Journal

ER -

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

Abstract

Bibliographical note

Funding

Keywords

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