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

^*Bu çalışma için yazışmadan sorumlu yazar

Kimya Bölümü

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

Araştırma sonucu: Dergiye katkı › Makale › bilirkişi

14 Atıf (Scopus)

Özet

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.

Orijinal dil	İngilizce
Sayfa (başlangıç-bitiş)	72-80
Sayfa sayısı	9
Dergi	European Polymer Journal
Hacim	104
DOI'lar	https://doi.org/10.1016/j.eurpolymj.2018.05.001
Yayın durumu	Yayınlandı - Tem 2018

Bibliyografik not

Publisher Copyright:
© 2018 Elsevier Ltd

Finansman

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

Finansörler	Finansör numarası
TUBITAK	111T075
National Council for Scientific Research

Belgeye Erişim

10.1016/j.eurpolymj.2018.05.001

Diğer Dosyalar ve Linkler

Link to publication in Scopus

Alıntı Yap

@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",

issn = "0014-3057",

publisher = "Elsevier Ltd",

}

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

Özet

Bibliyografik not

Finansman

Belgeye Erişim

Diğer Dosyalar ve Linkler

Parmak izi

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