Dithienobenzochalcogenodiazole-based electron donor-acceptor polymers for organic electronics

Amsalu Efrem; Yanlian Lei; Bo Wu; Mingfeng Wang; Siu Choon Ng; Beng S. Ong

doi:10.1016/j.dyepig.2016.01.035

Dithienobenzochalcogenodiazole-based electron donor-acceptor polymers for organic electronics

Amsalu Efrem, Yanlian Lei, Bo Wu, Mingfeng Wang^*, Siu Choon Ng, Beng S. Ong

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

13 Citations (Scopus)

Abstract

Appositely functionalized dithienobenzo-thiadiazole and dithienobenzo-oxadiazole-monomers were prepared and used in the synthesis of conjugated electron donor-acceptor (D-A) polymers. Detailed systematic investigations were carried out to study the effects of chalcogen atoms and three donor units on the optical and electrochemical properties as well as photovoltaic and field-effect transistor performance of the D-A polymers. All polymers displayed good thermal properties. Polymers containing benzooxadiazole moiety showed deeper LUMO levels as compared to their benzothiadiazole-containing analogues, whereas those derived from weak donor unit exhibited deeper HOMO levels than those with stronger donors. Photovoltaic power conversion efficiency of over 2% and hole field-effect mobility of 2.6 × 10^-2 cm²V^-1s^-1 and on/off ratio of over 10⁵ were obtained. These results demonstrate that dithienobenzo-chalcogenodiazole structures are potentially useful electron acceptor building blocks for the construction of D-A polymers for organic electronics applications.

Original language	English
Pages (from-to)	90-99
Number of pages	10
Journal	Dyes and Pigments
Volume	129
DOIs	https://doi.org/10.1016/j.dyepig.2016.01.035
Publication status	Published - 1 Jun 2016

Scopus Subject Areas

Chemical Engineering(all)
Process Chemistry and Technology

User-Defined Keywords

Dithienobenzochalcogenodiazole
Electron donor-acceptor polymers
Field-effect mobility
Field-effect transistors
Organic photovoltaics

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.dyepig.2016.01.035

Cite this

@article{0db88609e0164737aedd0ead340a17cd,

title = "Dithienobenzochalcogenodiazole-based electron donor-acceptor polymers for organic electronics",

abstract = "Appositely functionalized dithienobenzo-thiadiazole and dithienobenzo-oxadiazole-monomers were prepared and used in the synthesis of conjugated electron donor-acceptor (D-A) polymers. Detailed systematic investigations were carried out to study the effects of chalcogen atoms and three donor units on the optical and electrochemical properties as well as photovoltaic and field-effect transistor performance of the D-A polymers. All polymers displayed good thermal properties. Polymers containing benzooxadiazole moiety showed deeper LUMO levels as compared to their benzothiadiazole-containing analogues, whereas those derived from weak donor unit exhibited deeper HOMO levels than those with stronger donors. Photovoltaic power conversion efficiency of over 2% and hole field-effect mobility of 2.6 × 10-2 cm2V-1s-1 and on/off ratio of over 105 were obtained. These results demonstrate that dithienobenzo-chalcogenodiazole structures are potentially useful electron acceptor building blocks for the construction of D-A polymers for organic electronics applications.",

keywords = "Dithienobenzochalcogenodiazole, Electron donor-acceptor polymers, Field-effect mobility, Field-effect transistors, Organic photovoltaics",

author = "Amsalu Efrem and Yanlian Lei and Bo Wu and Mingfeng Wang and Ng, {Siu Choon} and Ong, {Beng S.}",

note = "Funding Information: M.W. is grateful for the start-up funding support of Nanyang Assistant Professorship by Nanyang Technological University . We gratefully acknowledge A*STAR , Singapore (Grant No. 102 170 0135 ) and Hong Kong Baptist University Strategic Development fund ( SDF13-0531-A02 ) for financial support. We thank Kai Wang and Marc Courte for help in AFM. ",

year = "2016",

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doi = "10.1016/j.dyepig.2016.01.035",

language = "English",

volume = "129",

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journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Elsevier BV",

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TY - JOUR

T1 - Dithienobenzochalcogenodiazole-based electron donor-acceptor polymers for organic electronics

AU - Efrem, Amsalu

AU - Lei, Yanlian

AU - Wu, Bo

AU - Wang, Mingfeng

AU - Ng, Siu Choon

AU - Ong, Beng S.

N1 - Funding Information: M.W. is grateful for the start-up funding support of Nanyang Assistant Professorship by Nanyang Technological University . We gratefully acknowledge A*STAR , Singapore (Grant No. 102 170 0135 ) and Hong Kong Baptist University Strategic Development fund ( SDF13-0531-A02 ) for financial support. We thank Kai Wang and Marc Courte for help in AFM.

PY - 2016/6/1

Y1 - 2016/6/1

N2 - Appositely functionalized dithienobenzo-thiadiazole and dithienobenzo-oxadiazole-monomers were prepared and used in the synthesis of conjugated electron donor-acceptor (D-A) polymers. Detailed systematic investigations were carried out to study the effects of chalcogen atoms and three donor units on the optical and electrochemical properties as well as photovoltaic and field-effect transistor performance of the D-A polymers. All polymers displayed good thermal properties. Polymers containing benzooxadiazole moiety showed deeper LUMO levels as compared to their benzothiadiazole-containing analogues, whereas those derived from weak donor unit exhibited deeper HOMO levels than those with stronger donors. Photovoltaic power conversion efficiency of over 2% and hole field-effect mobility of 2.6 × 10-2 cm2V-1s-1 and on/off ratio of over 105 were obtained. These results demonstrate that dithienobenzo-chalcogenodiazole structures are potentially useful electron acceptor building blocks for the construction of D-A polymers for organic electronics applications.

AB - Appositely functionalized dithienobenzo-thiadiazole and dithienobenzo-oxadiazole-monomers were prepared and used in the synthesis of conjugated electron donor-acceptor (D-A) polymers. Detailed systematic investigations were carried out to study the effects of chalcogen atoms and three donor units on the optical and electrochemical properties as well as photovoltaic and field-effect transistor performance of the D-A polymers. All polymers displayed good thermal properties. Polymers containing benzooxadiazole moiety showed deeper LUMO levels as compared to their benzothiadiazole-containing analogues, whereas those derived from weak donor unit exhibited deeper HOMO levels than those with stronger donors. Photovoltaic power conversion efficiency of over 2% and hole field-effect mobility of 2.6 × 10-2 cm2V-1s-1 and on/off ratio of over 105 were obtained. These results demonstrate that dithienobenzo-chalcogenodiazole structures are potentially useful electron acceptor building blocks for the construction of D-A polymers for organic electronics applications.

KW - Dithienobenzochalcogenodiazole

KW - Electron donor-acceptor polymers

KW - Field-effect mobility

KW - Field-effect transistors

KW - Organic photovoltaics

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U2 - 10.1016/j.dyepig.2016.01.035

DO - 10.1016/j.dyepig.2016.01.035

M3 - Journal article

AN - SCOPUS:84959440585

SN - 0143-7208

VL - 129

SP - 90

EP - 99

JO - Dyes and Pigments

JF - Dyes and Pigments

ER -

Dithienobenzochalcogenodiazole-based electron donor-acceptor polymers for organic electronics

Abstract

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